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Volume 25, Issue 11
Displaying 1-50 of 57 articles from this issue
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KAZUHIKO JUNI, MASAHIRO NAKANO, TAKAICHI ARITA1977 Volume 25 Issue 11 Pages 2807-2811
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPermeation of butamben through a silicone membrane was investigated for up to 120 hours in the presence of three complexing agents. The complexes formed between these agents and the drug, each having different stability constants, were considered to serve as reservoirs of the drug. Release-sustaining behavior was evaluated for the three cases in permeation experiments. The rank order of the sustaining power was in agreement with the order of stability of each complex. By employing an agent which forms a stable complex, much drug can be introduced to the solution system. A desired release profile of drug can therefore be achieved by proper choice of a complexing agent. Surfactant micelles are also expected to function as reservoirs of the drug. Among the three surfactants examined, dodecyltrimethylammonium chloride solubilized butamben to a significant extent and showed excellent sustained-release of the drug. Possible application of surfactants to sustained-release systems was indicated.View full abstractDownload PDF (583K) -
SHIKIFUMI KITAZAWA, IKUO JOHNO, HAJIME ITO1977 Volume 25 Issue 11 Pages 2812-2820
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe exsorption of sulfanilamide into the small intestinal lumen after intravenous administration of the drug was studed with perfusion solution without any drugs having three different tonicities such as hypotonicity (0.45%), isotonicity (0.90%), and hypertonicity (1.35%) with sodium chloride employing an in situ single perfusion method devised by Schanker and his co-workers. The intraluminal single perfusion was conducted principally at a rate of 1 ml/min. The exsorption rate of the drug into the isotonic perfusate was dose-dependent and the rate was decreased with time obeying the first-order kinetics as well as the decrease in blood level of the drug. The amount of the drug exsorbed in the isotonic perfusate for 180 min represented as the percentage of dose was almost constant (about 17%) in the dose rangs from 10 mg/kg to 50 mg/kg used in the present study. The effect of tonicity of perfusion solution on the exsorption was examined and it was found that the exsorption rate and the amount exsorbed in the perfusate of the drug were increased with increasing the tonicity of the perfusate. Although the exsorption rate and the amount exsorbed in the lumen were changed by different experimental conditions, the existence of the drug in the perfusate was not negligible. These evidences suggest that the small intestinal lumen may be an important organ in the distribution of the drug. Moreover, the excretion of the drug in the bile juice was remarkably smaller than the exsorption of the drug into perfusate. Hence it is able to conclude that the distribution of the drug in the small intestinal lumen might be conducted across the intestinal membrane rather than through the agency of bile juice.View full abstractDownload PDF (1067K) -
TAKAHARU MIZUTANI, POFENG KUO, AKIRA MIZUTANI1977 Volume 25 Issue 11 Pages 2821-2826
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCircular dichroism (CD) of the hypocalcemic protein purified from bovine parotid gland was studied under various conditions. The CD spectra and hypocalcemic activity were measured after incubation of the sample in 6.6 M urea or 6 M guanidine hydrochloride (Gdn-HCl) and subsequent removal of the denaturants by dialysis. The sample dialyzed after incubation in 6.6 M urea retained the hypocalcemic activity and its CD spectra were very similar to that of the native protein. The sample treated in the same way with 6 M Gdn-HCl had no activity, though its CD pattern was similar to that of the native protein. The pattern of thermal transition at [θ]222 of the urea-treated sample resembled that of the native protein but that of the Gdn-HCl-treated sample was slightly different from that of the navive protein. The CD pattern of the sample reduced with mercaptoethanol showed a slightly low α-helix content and the hypocalcemic activity was also low compared to the native protein. Scission of the peptide bond was not found from the results of polyacrylamide gel disc electrophoresis of these samples.View full abstractDownload PDF (948K) -
HIDETAKA YUKI, HIDEKI KAWASAKI, TOSHIKO KOBAYASHI, AKIRA YAMAJI1977 Volume 25 Issue 11 Pages 2827-2830
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA sensitive and selective analytical method for cytosine, 3-methylcytosine, and 5-methylcytosine in nucleic acids by high performance liquid chromatography was developed. This method involves hydrolysis of deoxyribonubleic acid (DNA) or ribonucleic acid (RNA) with perchloric acid at 100°for 1 hr, removal of the acid by weakly basic anion exchange resin (CG-4B, OH-form), separation of cytosine, 3-methylcytosine, and 5-methylcytosine from other bases by treatment with Dowex 1×2 column (HCOO-form), and the analysis of the eluate by high performance liquid chromatography. Recoveries were more than ninety percent. This method was applied to several nucleic acids, and molar ratio of 3-, and 5-methylcytosine to cytosine was obtained.View full abstractDownload PDF (574K) -
YASUHIRO YAMANE, HIDEKI FUKINO, YUKIO AIDA, MASAYOSHI IMAGAWA1977 Volume 25 Issue 11 Pages 2831-2837
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInteraction of methylmercury and selenium was studied in order to examine the mechanism of protective effects of selenium against the toxicity of methylmercury, mainly using methylmercuric chloride labeled with carbon-14. It was found that discharge of 14C into respiratory excretion was markedly accelerated by the concurrent administration of sodium selenite and 14C-labeled methylmercuric chloride, as compared with control of a sigle administration of 14C-labeled methylmercuric chloride. That is, the total amount of 14C discharged during 48 hr after the concurrent administration, was about 5.5 times as much as that in a single administration of 14C-labeled methylmercury. The acceleration of demethylation of methylmercury seemed to be more responsible for the action of selenium. Secodly, the uptake of methylmercury into erythrocytes, was examined and then, the amount of mercury in erythrocytes showed a tendency to become lower in the group given selenium. It was found that the uptake of methylmercury into erythrocytes was inhibited by about 30% with the administration of selenite.View full abstractDownload PDF (802K) -
TAKASHI HIROTA, TAKAJI KOYAMA, TETSUTO NANBA, MASATOSHI YAMATO1977 Volume 25 Issue 11 Pages 2838-2843
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Vilsmeier reaction of phenylacetonitriles to obtain intermediates of isoquinoline cyclization was described (refer to Chart 1). Phenylacetonitrile (I) gave β-dimethylamino-α-phenylacrylonitrile (II), α-formyl-(III) and α, N-diformyl- (IV) α-phenylacetamide, and 5, 7-dioxo-2, 6-diphenyl-4-aza-2-heptenamide (VI). m-Methoxyphenylacetonitrile (VII) gave α-(m-methoxyphenyl)-β-dimethylaminoacrylonitrile (VIII) and 3, 5-bis (m-methoxyphenyl)-6-(N, N-dimethylaminomethyleneamino)-2(1H)-pyridone (IX). p-Methoxyphenylacetonitrile (XI) gave 2-[α-(β-carbamoyl)-p-methoxystyryl) amino]-6-chloro-3, 5-bis(p-methoxyphenyl) pyridine (XII). 3, 5-Dimethoxyphenylacetonitrile (XIV) gave 3-chloro-6, 8-dimethoxyisoquinoline (XV) and 3-chloro-5-hydroxymethyl-6, 8-dimethoxyisoquinoline (XVI). Phenylacetamides (V, X, XIII, XVII) were also obtained from respective nitriles (I, VII, XI, XIV).View full abstractDownload PDF (712K) -
EIKO OHTSUKA, HISAYO TSUJI, TETSUO MIYAKE, MORIO IKEHARA1977 Volume 25 Issue 11 Pages 2844-2849
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious protecting groups were introduced to the phosphate of 2'-O-benzoyluridine 3'-phosphate. Stability and selective removal of these groups from the trisubstituted phosphate were investigated and nucleotides with trisubstituted phosphate were uesd for the synthesis of dinucleotides by condensation with a properly protected mononucleotide.View full abstractDownload PDF (824K) -
AKIRA MIZUTANI, TAKAHARU MIZUTANI, P-FENG KUO1977 Volume 25 Issue 11 Pages 2850-2855
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hypocalcemic protein purified from bovine parotid gland was modified with chemical reagents or by digestion with carboxypeptidase A, the hypocalcemic activities of the treated samples were assayed, and the effect of treatments was examined statistically. Cleavage of the tryptophanyl and tyrosyl residues in the sample was oxidatively done with N-bromosuccinimide, and tyrosyl residues were acetylated with N-acetylimidazole. In both treatmets, the hypocalcemic activities of the treated samples were somewhat low compared to the controls but the effect of the treatments was not significant. However, both treatments in the presence of urea became effective. Oxidation of methionyl residues of the sample with hydrogen peroxide resulted in the retention of the activity, and the effect of oxidation in the presence of urea was not significant. In the modification of free amino groups, the treatment was ineffective when 51.6% of lysyl free amino groups was blocked with trinitrobenzenesulfonic acid, but the effect appeared when free amino groups were eliminated with nitrous acid. After the reduction of disulfide bonds of the sample with 2-mercaptoethanol, the resulting SH residues were modified with 5, 5'-dithiobis (2-nitrobenzoic acid), and the histidyl residues of the sample were acylated with ethoxyformic anhydride, by which effect of these treatments became significant. The sample was digested with carboxypeptidase A at 25°for 4 hr failed to show effect of the treatment. From these results, tryptophanyl, tyrosyl, free amino, disulfide, and histidyl residues may play a role in appearance of the hypocalcemic activity.View full abstractDownload PDF (830K) -
NOBUO MOCHIZUKI, SHOJI OKADA, OSAMU TAMEMASA1977 Volume 25 Issue 11 Pages 2856-2861
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of DNA-interacting aminoquinones, 2-amino-1, 4-naphthoquinone imine (ANQI), 2, 5-diamino-1, 4-naphthoquinone imine (DANQI) and 2-hydroxyamino-1, 4-naphthoquinone (HANQ), which had been reported to cellular DNA synthesis in Ehrlich ascites carcinoma and E. coli, was studied on cell-free DNA and RNA syntheses catalyzed by E. coli DNA polymerase I and RNA polymerase, respectively. These aminoquinones inhibited both the polymerase reactions to a similar degree (30-56% at 1×10-3M). The inhibition of DNA synthesis was in nearly the same extent as that observed in E. coli whole cells, but lower than that found in intact cells of Ehrlich ascites carcinoma. The inhibition of the DNA polymerase reaction by the aminoquinones was competitive with calf thymus DNA used as the template. Any of the aminoquinones received higher spectral change by the native DNA than by the heat-denatured, and also more inhibited the DNA synthesis directed by the double-stranded DNA than that by the single-stranded. These results suggest that the inhibition is due to the interaction between the DNA and the aminoquinones.View full abstractDownload PDF (658K) -
HIROSHI KOBAYASHI, YUJI MIYOSHI, KOICHI KITAMURA, YAEKO YOSHIZAKI, SHO ...1977 Volume 25 Issue 11 Pages 2862-2869
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of ethanol on the intramuscular absorption of water-soluble drugs from the rat thigh muscle was investigated. The presence of ethanol caused a pronounced decrease in the absorption rate of drugs, and the reduction was reflected by the decrease in plasma concentrations. It was also found that the absorption rate of drugs from the site of injection depends mainly on the concentration rather than the absolute amount of ethanol. A direct relationship between the relative viscosity of the injectable solution and the inhibitory absorption was demonstrated at lower concentrations of ethanol, but not at higher concentration. This shows that the inhibitory absorption effect of ethanol cannot be adequately explained by simple physicochemical factors, such as viscosity, but the existence of other factors must be acting. A constant intravenous infusion of ethanol showed no effect on the intramuscular absorption of drug. Furthermore, ethanol did not significantly change the permeability of the isolated mesentery to drug molecules. On the other hand, the connective tissue permeability was significantly decreased by the presence of ethanol and had a good correlation to the inhibitory effect of ethanol on the intramuscular absorption of drugs. From these observations, it can be concluded that the mechanism of the inhibitory effect of ethanol is mainly due to its influence on the extracellular spaces and the connective tissues permeability.View full abstractDownload PDF (838K) -
ATSUSHI MURAKAMI, YUKIO AKAHORI1977 Volume 25 Issue 11 Pages 2870-2874
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe computer experiments were carried out on the physiologically active compounds of prostaglandins : PGE1, 15-epi PGE1, 11-epi PGE1, 11, 15-epi PGE1, PGA1, 15-epi PGA1, PGF1α, PGF1β, and PGB1. Sterically allowed conformations and their conformational energies were calculated, and correlation between the conformation and biological potencies of the prostaglandins was examined. The pair of isomers, PGE1 and 15-epi PGE1, has equal number of sterically allowed conformations and similar range of conformational energies, but the distribution of conformational energies and the conformation near the five-membered ring are quite different. Data on 11-epi PGE1, and 11, 15-epi PGE1 or PGA1 and 15-epi PGA1 were also in the same pattern. The conformation near the five-membered ring are restricted except in PGB1. Orientation of the hydroxyl group bonded to C15 affects orientation of the side chain of prostaglandins. Importance of the orientation of the hydroxyl group and of the conformation near the five-membered ring was suggested.View full abstractDownload PDF (556K) -
SHINZO KANO, TSUTOMU YOKOMATSU, SHIROSHI SHIBUYA1977 Volume 25 Issue 11 Pages 2875-2881
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 1-(2-bromo-4, 5-dimethoxyphenethyl)-2, 3, 4, 5-tetrahydro-7, 8-dimethoxy-2-methyl-1H-2-benzazepine (7a) with dimsylsodium afforded 5, 6, 7, 8, 13, 14-hexahydrotrans-13, 14-methano-2, 3, 10, 11-tetramethoxy-5-methyldibenzo [b, f] azecine (8) and its cisisomer (9). The structure of the former was confirmed by direct comparison with the authentic sample prepared by the Simmons-Smith reaction of the 13, 14-trans-5, 6, 7, 8-tetrahydrodibenzo [b, f] azecine (11). 5, 6, 7, 8, 13, 14-Hexahydro-11-hydroxy-cis-13, 14-methano-2, 3, 10-trimethoxy-5-methyldibenzo [b, f] azecine (15) was obtained by the reaction of 1-(2-bromo-4, 5-dimethoxyphenethyl)-2, 3, 4, 5-tetrahydro-8-hydroxy-7-methoxy-2-methyl-1H-2-benzazepine (7b) with dimsylsodium. The same reaction by the use of 1-(2-bromo-4, 5-dimethoxyphenethyl)-2, 3, 4, 5-tetrahydro-7-hydroxy-8-methoxy-2-methyl-1H-2-benzazepine (7e) afforded the 13-(methylsulfinyl) methyl-5H-dibenzo [b, g] azacycloundecine (16).View full abstractDownload PDF (735K) -
AKIRA KONO1977 Volume 25 Issue 11 Pages 2882-2886
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCobalt chelate of bleomycin (Co-BLM) bound deoxyribonucleic acid (DNA) was purified from Ehrlich solid tumor of mice administered with Co-BLM by the extraction from the purified nuclei. In both 57Co-BLM and Co-BLM (14C), the DNA was taken in 99% purity, and the decrease in the specific radioactivity of the Co-BLM=DNA complex was minimized in the course of the purification procedure. The complex was stable in the Sephadex G-100, hydroxyapatite columns and neutral sucrose gradient solution. Moreover, this was stable in the electrophoretic conditions. However, Co-BLM dissociated from DNA by acid, alkaline or heat treatment.View full abstractDownload PDF (645K) -
TOZO FUJII, MASASHI OHBA, SHIGEYUKI YOSHIFUJI, MAKOTO KIRISAWA1977 Volume 25 Issue 11 Pages 2887-2894
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the alkaline ferricyanide oxidation at 32°of 3-substituted 1-(3, 4-dimethoxyphenethyl) pyridinium bromides (type 3), the hydroxymethyl, N, N-dimethylaminomethyl, carbamoyl, and 1, 1-ethylenedithioethyl groups at the 3-position have been found to orient the oxidation to both the 2-(type 4) and the 6-position (type 5) in ratios of 70 : 30, 26 : 74, 50 : 50, and 4 : 96. The carboxyl or 1, 1-ethylenedioxyethyl group at the 3-position has oriented the oxidation to the 6-position exclusively, and possible factors in determining the regioselectivity in the ferricyanide oxidation of the 1, 3-disubstituted pyridinium salts are discussed. For preparation of additional pyridone derivatives, 1-(3, 4-dimethoxyphenethyl)-5-carboxy-2(1H)-pyridone (5d) was esterified with methanolic hydrogen chloride to the methyl ester (5h), and 1-(3, 4-dimethoxyphenethyl)-5-(1, 1-ethylenedioxyethyl)-2 (1H)-pyridone (5e) was converted into the methyl ketone (5i) by acid hydrolysis. The structures of the pyridones (4a, b, c, f, 5a-i) thus prepared have assigned on the basis of their ultraviolet, infrared, and nuclear magnetic resonance spectra.View full abstractDownload PDF (1027K) -
KAZUO YAMASAKI, HIROSHI KOHDA, TOSHIKO KOBAYASHI, NORITO KANEDA, RYOJI ...1977 Volume 25 Issue 11 Pages 2895-2899
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the aerial part of Stevia paniculata (Compositae), five new diterpene glucosides, named paniculosides I-V (5-9) were isolated. On comparison of 13C nuclear magnetic resonance spectra of these glucosides with those of the aglycones, ent-15α-hydroxykaur-16-en-19-oic acid (1) [as methyl ester (17)], ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid (2), ent-11α, 15α-dihydroxykaur-16-en-19-oic acid (3), and ent-16β, 17-dihydroxykauran-19-oic acid (4) as well as some model glucosides, paniculosides I-IV (5-8) can be formulated as β-glucopyranosyl ester of 1, 3, 2, and 4, respectively and paniculoside-V (9) can be represented by 15-O-β-glucopyranoside of 5.View full abstractDownload PDF (682K) -
AKIRA TAKAMIZAWA, TSUYOSHI IWATA, SAICHI MATSUMOTO1977 Volume 25 Issue 11 Pages 2900-2909
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInvestigations on the urinary metabolites of isophosphamide, 4-hydroxyisophosphamide and 4-hydroxyisophosphamide including stereoisomers of the C4-oxidized derivatives in rabbits revealed that their metabolic behaviors were different from each other and also form those of cyclophosphamide. Administration of isophosphamide to rabbits resulted in the urinary excretion of carboxyisophosphamide and two N-dechloroethylated metabolites besides considerable amount of unchanged isophosphamide, while 4-hydroxyisophosphamide was metabolized principally into carboxyisophosphamide. In the case of 4-hydroxyisophosphamide, carboxyisophosphamide was excreted as a major metabolite, but considerable amount of a new metabolite which might be produced from 4-ketoisophosphamide via a hitherto unknown pathway was also excreted besides small amount of 4-ketoisophosphamide. Mechanism of the formation of this new metabolite was proposed based on the chemical conversion of a suggested intermediate into the metabolite. PHosphorus configuration of the C4-oxidized isophosphamides was found to have no significant effect upon their metabolism. It was suggested that the results of the present studies could account for the great differences in in vivo antitumor activities between isophosphamide and its pre-activated derivatives and also between isophosphamide and cyclophosphamide.View full abstractDownload PDF (1216K) -
MASASHI TOMODA, NORIKO SATOH1977 Volume 25 Issue 11 Pages 2910-2916
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPartial acid hydrolysis of paniculatan, the mucous polysaccharide isolated from the inner barks of Hydrangea panculata SIEB., has led to the isolation of five oligosaccharides. Analysis of components, reduction and methylation, and partial degradation studies provided the evidences that they are O-α-(4-O-methyl-D-glucopyranosyluronic acid)-(1→4)-D-galactopyranose, O-α-(D-galactopyranosyluronic acid)-(1→2)-L-rhamnopyranose, O-α-(D-galactopyranosyluronic acid)-(1→2)-O-α-L-rhamnopyranosl-(1→2)-L-rhamnopyranose, O-α-(D-galactopyranosyluronic acid)-(1→2)-O-α-L-rhamnopyranosyl-(1→4)-O-α-(D-galactopyranosyluronic acid)-(1→2)-L-rhamnopyranose, and O-α-(D-glucopyranosyluronic acid)-(1→3)-O-α-(D-galactopyranosyluronic acid)-(1→2)-L-rhamnopyranose. From the accumulated evidence, a possible structure of the polysaccharide was proposed.View full abstractDownload PDF (791K) -
KATSUMI ITOH, MICHIO MOTOHASHI, HISASHI KURIKI, HIROSADA SUGIHARA, NOB ...1977 Volume 25 Issue 11 Pages 2917-2928
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of N-substituted 2-amino-5, 6-dihydroxy-1, 2, 3, 4-tetrahydro-1-naphthalenols (1), which are comformationally rigid derivatives of adrenergic catecholamine, were synthesized via three routes ; namely, the synthetic route in which the final step is 1) the reduction of 1-carbonyl group, 2) N-substitution by reductive alkylation of 2-amino group, or 3) removal of protecting groups of the catechol moiety. Several pairs of 1, 2-cis and trans isomers of 1 were prepared by stereoselective reactions or by separation of each stereoisomer with column chromatography or fractional crystallization. Thus, transamino alcohol (9-trans) was afforded by reduction of 2-amino-5, 6-dibenzyloxy-3, 4-dihydro-1 (2H)-naphthalenone (13) with sodium borohydride, while the cis isomer (9-cis) was obtained from 7, 8-dibenzyloxy-1, 2-dihydronaphthalene (19) via an aziridine intermediate. Several of 1 exhibited excellent β2-adrenoceptor activity superior to l-isoproterenol, the trans derivative being more potent than the cis isomer.View full abstractDownload PDF (1423K) -
HIROSHI IRIE, NOBUTAKA FUJII, HIROSHI OGAWA, HARUAKI YAJIMA, MASAHIKO ...1977 Volume 25 Issue 11 Pages 2929-2934
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAromatic ethers, such as anisole or phenetole, were cleaved smoothly with methanesulphonic acid (MSA) or trifluoromethanesulphonic acid in the presence of Met to form methionine-S-methyl (or ethyl) sulphonium salt (I). When the protecting group of Z-Met-OH or Boc-Met-OH was cleaved in the MSA-anisole system, (I) was found as a major product, besides a samll amount of S-benzyl or S-tert-butyl derivative. Thus a Met-containing peptide, H-Tyr-Gly-Gly-Gly-Lys-Met-Gly-OH named endorphin, was synthesized after deprotection of Z (OMe)-Tyr-Gly-Gly-Gly-Lys (Z)-Met (O)-Gly-OH by the MSA-anisole procedure followed by reduction of the Met (O) moiety to the parent amino acid residue with dithiothreitol.View full abstractDownload PDF (832K) -
MASAYUKI ONDA, YOSHIHIRO HARIGAYA, TSUTOMU SUZUKI1977 Volume 25 Issue 11 Pages 2935-2941
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to obtain the 11-oxygenated benzo [c] phenanthridines photolyses of the 1, 2-dihydroisoquinoline (1), the isocarbostyril (3) and its enol acetates (7) and (8) are examined. The 1, 2-dihydroisoquinoline (1) and the isocarbostyril (3) do not give the expected compounds. The enol acetates (7) and (8) afford the 11-acetoxybenzo [c] phenanthridines (10) and (11). On hydrolysis and successive oxidation, 10 affords the quinone (13) which is thought to be an intermediate for synthesis of the chelidonine-like compound.View full abstractDownload PDF (787K) -
NAOKI SHIMIDZU, TOYOZO UNO1977 Volume 25 Issue 11 Pages 2942-2947
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe acid dissociation constants of 2-, 4-and 7-substituted benzothiazole derivatives and the formation constants of the complexes formed by these ligands with Mg2+, Cu2+, Ni2+, Co2+, Zn2+, Mn2+ and Cd2+ were determined potentiometrically at 25°in 2/1 (v/v) dioxane/water solution. The order of the basicity of the ligands is 4-substituted > 7-substituted > 2-substituted benzothiazole derivatives. Also the basicity of the benzothiazole derivatives, substituted at the same position, is in the order : aminomethyl > azomethine > azo compounds. Except for the azonaphthol derivatives, a linear relationship exists between the basicity and the π electron density of the hydroxyl group of the ligands, which may suggest that hydrazone form is predominant in the azo-hydrazone tautomerism of the benzothiazolylazonaphthol derivatives. The stability of the metal complexes corresponds to the basicity of the ligands and the log KML values approximately follow the Mellor-Maley stability sequence. It is expected that the benzothiazolylazo derivatives would be good metallochromic indicators in chelatometric titrations with ethylenediaminetetraacetic acid as titrant.View full abstractDownload PDF (663K) -
KIYOSHI TATSUMI, SHIGEYUKI KITAMURA, HIDETOSHI YOSHIMURA1977 Volume 25 Issue 11 Pages 2948-2952
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1) The in vitro reduction of 14C-2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide (AF-2) and 14C-nitrofurazone by xanthine oxidase-hypoxanthine resulted in the formation of their active metabolites capable of binding to desoxyribonucleic acid (DNA), ribonucleic acid (RNA) and protein. 2) The distribution and excretion of radioactivity in various tissues, gastrointestinal contents, feces and urine were examined after oral administration of 14C-AF-2 to rats. 3) The in vivo binding of 14C-AF-2 and 14C-nitrofurazone to liver protein, DNA and ribosomal RNA, and to kidney protein was demonstrated in rats given orally these drugs.View full abstractDownload PDF (687K) -
TADAO FUJITA, TAKEICHI SAKAGUCHI1977 Volume 25 Issue 11 Pages 2953-2958
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mixed ligand complexes, Cu22+ (AdeH)2 (phen)2X2·2H2O, where X is Cl, Br and ClO4, have been prepared from aqueous solution. The complexes were characterized by elementary and infrared spectroscopic analyses. In this paper, the IR spectra of these compounds were discussed in some detail and compared to those of binary parent complexes. It was supposed that N9 of adenine ligand coordinated to Cu2+ from infrared (IR) spectra. The electron paramagnetic resonance (EPR) spectra of the mixed ligand complexes were recorded on polycrystalline samples at room temperature and g-values of the compounds were obtained.View full abstractDownload PDF (664K) -
HIDENARI SHIGEMATSU, YUKIO KUROIWA, HIDETOSHI YOSHIMURA1977 Volume 25 Issue 11 Pages 2959-2963
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFollowing the previous studies, the present investigation was undertaken to obtain definite evidence suporting the participation of cytochrome b5 in reduced nicotinamide adenine dinucleotide (NADH)-dependent deethylation of p-nitrophenetole with rabbit liver microsomes in vitro. The results obtained are as follows : 1) Treatment of liver microsomes with trypsin resulted in decrease of cytochrome b5 concentration in parallel with decrease of the activity of NADH-dependent of p-nitrophenetole with rabbit liver microsomes. 2) The oxidation of rduced cytochrome b5 was stimulated by the presence of p-nitrophenetole. 3) The NADH-dependent deethylation of p-nitrophenetole with rabbit liver microsomes was strongly inhibited by a rabbit antiserum which was prepared against rat liver microsomal cytochrome b5. From these observations, it was concluded that cytochrome b5 was an obligatory component in the NADH-dependent deethylation of p-nitrophenetole.View full abstractDownload PDF (672K) -
YOSHIYASU TERAO, KOJI MATSUNAGA, MINORU SEKIYA1977 Volume 25 Issue 11 Pages 2964-2968
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new route to the preparation of α-alkyl (or aryl) thiosubstituted nitrosamines has been provided by nitrosation of alkylaminomethyl alkyl (or aryl) sulfides obtained simply from primary amine hydrochlorides, formaldehyde, and alkyl (or aryl) thioalcohols. By oxidation with metaperiodate and permanganate the corresponding sulfoxides and sulfones have been obtained, respectively. Compositions of the syn and anti isomers of the nitrosamines are determined by NMR technique.View full abstractDownload PDF (590K) -
TOSHIO NAMBARA, HIROSHI HOSODA, KYOICHI TADANO, KOUWA YAMASHITA, NORIK ...1977 Volume 25 Issue 11 Pages 2969-2973
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to obtain the specific antiserum used for radioimmunoassay of testosterone a new hapten-carrier conjugate was prepared from 15α-hydroxytestosterone 15-hemisuccinate by coupling with bovine serum albumin employing the mixed anhydride technique. The specificity of anti-testosterone antiserum elicited in the rabbit by immunization with this antigen was tested by cross-reaction studies with the related steroids. The results indicated that specific antiserum which is capable of differentiating testosterone from 5α-dihydrotestosterone and androstenedione to a certain extent would be produced by antigen whose steroidal moiety is coupled ot a coupled to a protein through the position remote from the inherent functional groups.View full abstractDownload PDF (660K) -
RYUJI MARUMOTO, YOSHIYASU FURUKAWA1977 Volume 25 Issue 11 Pages 2974-2982
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDie Umsetzung von 4-Hydroxyamino-uracilen (2) mit Saureanhydriden sowie Orthocarbonsaureestern in Gegenwart von Basen ergibt in guter Ausbeute Isoxazolo [3, 4-d]-pyrimidin-4, 6 (5H, 7H)-dione (3). Das intermediar gebildete 5-Acyl-4-acyloxyaminouracil (8) wurde isoliert und in 3 ubergefuhrt. Bei der Umsetzung von 4-Hydroxyamino-1, 3-dimethyl-uracil (2b) mit Chlorameisensaureester in Gegenwart von Pyridin entsteht Pyrido [1', 2' : 2, 3] pyrazolo [5, 4-d] pyrimidin (10), deren Konstitution an Hand spektroskopischer Methoden aufgeklart wird.View full abstractDownload PDF (931K) -
HIROSHI SHIMENO, SHINJI SOEDA, ATSUO NAGAMATSU1977 Volume 25 Issue 11 Pages 2983-2987
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1) Anti-inflammatory activities of pyridylalanine analogues were more potent than phenylbutazone (PB) in the carrageenin-induced rat paw edema test. dl-3-Pyridylalanine (3-PA) was 3 times more active than dl-2-pyridylalanine (2-PA) and 4 times more active than dl-4-pyridylalanine (4-PA) in this test. 2) The effects of PA analogues on the development of granuloma were studed in adrenalectomized rats by the cotton pellet medthod. 2-PA reduced the development of granuloma when given singly to rats. A simultaneous administration of 2-PA with cortisone clearly enhanced the anti-granulomatous action of cortisone. A single administration of 3-PA did not affect the development of granuloma, while a simultaneous administration of 3-PA with cortisone inhibited the action of cortisone. 4-PA had no effect on the action of cortisone and it did not affect the granuloma formation when administered alone. 3) The effects of PA analogues on the exudation were examined by the granuloma pouch method, using non-adrenalectomized rats. Among the PA analogues, only 2-PA showed a significant anti-exudative action when given singly to rats. The action of 2-PA was more active than that of PB, but less active than cortisone. The action of cortisone was enhanced by 2-PA, however, hardly affected by simultaneous administration of 3-PA or 4-PA.View full abstractDownload PDF (610K) -
HIROSADA SUGIHARA, KIYOSHI UKAWA, HISASHI KURIKI, MASAO NISHIKAWA, YAS ...1977 Volume 25 Issue 11 Pages 2988-3002
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn connection with our earlier studies on β-adrenergic-stimulating activities of ringclosed analogs of β-hydroxycatecholamines, a series of 2-amino-and 2-alkylamino-1, 2, 3, 4-tetrahydro-1-naphthalenols was synthesized with the aim of finding new bronchodilators with minimal cardiovascular side effects. The present paper includes compounds possessing a hydroxy group at the 6-position and a hydroxymethyl, cyano or ureidomethyl group at the 5-position. As starting materials, 6-methoxy-3, 4-dihydro-1 (2H)-naphthalenone and methyl 2-hydroxy-1-naphthoate were used. The latter was more advantageous for the synthesis of 5-hydroxymethyl derivatives. Stereoselective reduction of the 1-ketone to give cis-or trans-2-amino-1-hyroxy compounds was also discussed.View full abstractDownload PDF (1624K) -
TAKEKI OKUMOTO, NORIKO SUGIMOTO, HIROSHI IMAMURA1977 Volume 25 Issue 11 Pages 3003-3008
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the cross-resistance studies in vitro and in vivo, three sublines of Yoshida sarcoma with high resistance to nitrogen mustard (HN2) were highly susceptible to improsulfan, and there was no significant difference in the extent of improsulfan uptake and its binding to desoxyribonucleic acid between the original and HN2-resistant cells. The results obtained by the transport study of improsulfan at a dose range of 0.01 to 1 mM suggest that improsulfan uptake is non-active by Yoshida sarcoma cells. The factors of resistance to HN2 demonstrated in these resistant cells may not serve as factors of resistance to improsulfan.View full abstractDownload PDF (668K) -
YOSHIRO KOBAYASHI, ITSUMARO KUMADAKI, YUJI HANZAWA1977 Volume 25 Issue 11 Pages 3009-3012
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2- and 3-(Trifluorometyl) benzofurans (III and V) were synthesized by the reaction of 2-and 3-bromobenzofurans with trifluoromethyliodide in the presence of copper powder. Reaction of III and V with alcoholic sodium hydroxide, lithium aluminum hydride, and sodium amide showed that the trifluoromethyl group on the benzofuran ring is much less reactive than that on the indole ring. The remarkable point of reactions of the (trifluoromethyl) benzofurans is the addition of the nucleophile of C2, C3-double bond, which might be ascribed to the localization of the double bond.View full abstractDownload PDF (543K) -
EIICHI FUJITA, MASAHITO OCHIAI1977 Volume 25 Issue 11 Pages 3013-3017
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy the two successive oxidative rearrangements using thallium trinitrate, ent-16-kaurene (1) was stereoselectively converted into ent-16α-kauran-17-oic acid (30). Further application of these reactions led to a convenient transformation of ent-16-kauren-19-oic aicd (31) into ent-16α-kaurane-17, 19-dioci acid (32).View full abstractDownload PDF (653K) -
NARUHITO MASAI, MICHIO KIMURA, MICHIHIRO YAMAMOTO, TOSHIYUKI HIROHASHI ...1977 Volume 25 Issue 11 Pages 3018-3022
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 13C NMR spectra of twelve 1-cyclopropylmethyl-4-phenyl-2 (1H)-quinazolinones including a potent anti-inflammatory agent SL-573 were investigated, and the all carbon resonances were assigned mainly by the off-resonance technique, substituent effects on the 4-phenyl groups and 13C -19F couplings. It is noteworthy that the good correlations were found between Hammett parameters δp and the 13C chemical shifts of the para-substituted quinazolinone (1 and 7-12)-frame carbons in spite in spite of the large dihedral angles between the quinazolinone and phenyl ring planes (42.8°for SL-573).View full abstractDownload PDF (568K) -
TATSUO NAGASAKA, SADAO OHKI1977 Volume 25 Issue 11 Pages 3023-3033
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA convenient synthetic method for cycloalkanon [c, d] indoles (1 and 8) and some of their reactions were examined. The Friedel-Crafts reaction of 1-acetylindol-3-ylpropionic acids (4b and 4c) gave cyclopent [b] indoles (5b and 5c). This result indicates the general tendency of cyclization of 1-acetylindol-3-ylalkanoic acid, different from only one example reported previously by Szmuszkovicz, who prepared benz [c, d] indole derivative (3) from 1-acetylindol-3-ylsuccinic anhydride (2). The Friedel-Crafts reaction of 2-ethoxycarbonylindol-3-ylalkanoic acids (7b, 7c, and 7b), which were obtained in a good yield from easily available starting materials, gave cycloalkanon [c, d] indoles (8a, 8c, and 8e) in 24, 66, and 73% yield, respectively. Saponification and decarboxylation of 8a and 8e gave Uhle's ketone (1a) and a new ketone (1b), respectively. The Beckmann rearrangement of oximes (9a and 9b) with polyphosphoric acid gave lactams (10a and 10b) resulting from aryl migration. This is different from Bowman's example, in which lactams (11a and 11b) resulting from alkyl migration are obtained by the Beckmann rearrangement of oximes (9c and 9b) with thionyl chloride. Saponification and decarboxylation of 10a and 10b gave azepino [c, d] indolone (10c) and azocino-[c, d] indolone (10d) in 50 and 55% yield, respectively. 5-(3-Ethoxycarbonyl-5-oxo-2-pyrrolin-1-yl)-6 (1H)-oxo-3, 4, 5, 6-tetrahydrocyclohept-[c, d] indole (15b) was obtained from 1b by Stoll's method and its structure was elucidated from its nuclear magnetic resonance and mass spectra.View full abstractDownload PDF (1378K) -
TARO OGISO, SANAE OUE, HIROYUKI MASUDA1977 Volume 25 Issue 11 Pages 3034-3041
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn attempt has been made to prevent drug-induced hemolysis and to clarify the mechanism of the protective effective of chondroitin sulfate. As a result of these studies, it was found that chondroitin sulfate (10-4 and 5×10-4M) had a protective effect on chlorpromazine-induced hemolysis and K+ efflux. Scanning electron microscopic observations indicated that chondroitin sulfate reduced the cell swelling at relatively lower concentrations of chlorpromazine and significantly prevented the shrinking and sinking of the cells at higher concentrations. The erythrocytes pretreated with chondroitin sulfate, however, had little protective effect against osmotic and heat-induced hemolysis. The experiment on 1-anilinonaphthalene-8-sulfonate bindig to the ghosts pretreated with chondroitin showed that the hydrophobic environment of the membrane was not significantly affected by the exposure. The cells aggregated in the medium with chondroitin sulfate added, probably due to electrostatic repulsion. The aggregation appears partially to protect the cells from contact with the drug, as indicated by the data that chondroitin sulfate at 10-4 and 5×10-4M slightly blocked the binding of the cell membrane, and to decrease drug-induced hemolysis. Another protecting effect is ascribed to the inhibitory effect of the compound on hemoglobin diffusion.View full abstractDownload PDF (1490K) -
TOZO FUJII, MASASHI OHBA, SHIGEYUKI YOSHIFUJI1977 Volume 25 Issue 11 Pages 3042-3048
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-(3, 4-Dimethyoxyphenyl)-2-(3-substituted piperidino) ethanols (3a-d), which carry the carbamoyl, methoxycarbonyl, acetyl, and 1, 1-ethylenedioxyethyl group as the 3-substituent in the piperidine ring, have been prepared from 3-substituted pyridines (type 1) through 1-(3, 4-dimethoxyphenacyl) pyridinium bromides (type 2). In the mercuric acetate-EDTA oxidation of 3a-d, these 3-substituents have been found to orient the lactam carbonyl formation to the 6-position almost exclusively. It is suggested that the 3-substituents exert both steric and electronic effects.View full abstractDownload PDF (951K) -
YOSHIAKI WATANABE, SHUICHI SANADA, AKIHIRO TADA, JUNZO SHOJI1977 Volume 25 Issue 11 Pages 3049-3055
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOphiopogonin A, B', C, C', and D', the minor oligosides of Ophiopogonis tuber (tuber of Ophiopogon japonicus KER-GAWLER var. genuinus MAXIM.), have been isolated. The structures of these oligosides have been established as follows : ophiopogonin A (III) : ruscogenin 1-O-[(3-O-acetyl)-α-L-rhamnopyranosyl (1→2)]-β-D-fucopyranoside, ophiopogonin B'(IV) : diosgenin 3-O-[(4-O-acetyl)-α-L-rhamnopyranosyl (1→2)] [β-D-xylopyranosyl (1→3)]-β-D-glucopyranoside, ophiopogonin C (V) : mono-O-acetylophiopogonin D, ophiopogonin C'(VI) : diosgenin 3-O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranoside (=prosapogenin A of dioscin), ophiopogonin D'(VII) : diosgenin 3-O-[α-L-rhamnopyranosyl-(1→2)] [β-D-xylopyranosyl (1→3)]-β-D-glucopyranoside.View full abstractDownload PDF (888K) -
TAKASHI HIROTA, TAKAJI KOYAMA, CHIZUKO BASHO, TETSUTO NANBA, KENJI SAS ...1977 Volume 25 Issue 11 Pages 3056-3060
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyrimidine formation from active methyl group on heterocycles is described. 2-Methyl-pyridine (I), -quinoline (III), -pyrazine (IX), -benzothiazole (XX), 2, 4-dimethylquinoline (VII), and-thiazole (XIII) were successful in pyrimidine formation. 2-Methylimidazole (XI), -benzimidazole (XV), -benzoxazole (XVI), and 2, 4-dimethyloxazole (XII) were unsuccessful. Compound (III) gave pyrazine (V) and pyridine (VI) derivatives and pyridine formation occurred also in XX.View full abstractDownload PDF (648K) -
MASASHI TOMODA, YOKO SUZUKI1977 Volume 25 Issue 11 Pages 3061-3065
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA representative mucilage, named Abelmoschus-mucilage M, has been isolated from the roots of Abelmoschus manihot MEDICUS. It was homogeneous by ultracentrifugal analysis and on cellulose acetate membrane electrophoresis, and its water solution gave the high intrinsic viscosity value of 33.0. It was composed of 82% of polysaccharide and approximately 17% of protein, and molecular weight of its ammonium salt was estimated to be 25300. Its carbohydrate part was composed of L-rhamnose : D-galacturonic acid : D-glucuronic acid in the molar ratio of 1.2 : 1.0 : 1.0. The mucilage has been subjected to the reduction of carboxyl groups, and the result of methylation analysis of the product revealed the structural feature of the polysaccharide moiety in it.View full abstractDownload PDF (764K) -
AKIO MIYAKE, HISASHI KURIKI, NORIO TADA, MASAO NISHIKAWA, YOSHIKAZU OK ...1977 Volume 25 Issue 11 Pages 3066-3074
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 2-substituted amino-5-amino-6-hydroxy-1, 2, 3, 4-tetrahydro-1-naphthalenols (2) was synthesized starting with 6-methoxy-3, 4-dihydro-1 (2H)-naphthalenone (3). Thus, 6-hydroxy-tetralone (4), prepared by demethylation of 3, was nitrated to give a mixture of 5-nitro (5) and 7-nitro (6) derivatives. Compound 5 was led to the oxime tosylate (9) via compounds 7, 8. Neber rearrangement of 9 into α-amino ketone (10) followed by reduction with sodium borohydride afforded trans-2-amino-6-benzyloxy-5-nitro-1, 2, 3, 4-tetrahydro-1-naphthalenol (11), from which compounds 2a, 2b and 2d-r were derived. The 2-methylamino derivative (2c) was prepared via two alternative routes. Most of the compounds 2 exhibited potent β-adrenoceptor agonistic activity with considerable β2-selectivity. However, compound 24, a position isomer of 2d which was prepared from 6 by the similar procedures, showed no β-adrenoceptor activity.View full abstractDownload PDF (1078K) -
KIYOKAZU TAKAISHI, HIROSHI KUWAJIMA, HIROKO HATANO, HIROMI GO1977 Volume 25 Issue 11 Pages 3075-3077
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyanogenic glycosides-prunasin (I) and amygdalin (II)-were isolated in crysatalline from Sorbus commixta, S. gracilis, S. sambucifolia, and S. matsumurana ; the glycosides were found in all tissues of the plant. The contents of the glycosides of Sorbus spp. distributed at higher elevation was more abundant than those of the Sorbus spp. at lower elevation. The contents of I and II were the most abundant in seeds (0.189%) and, among them, the content of I was ten times more than that of II in the plants. The activity of the glycosidase in the seeds was about ten times as high as that in other tissues.View full abstractDownload PDF (499K) -
HIROSHI KOBAYASHI, YUJI MIYOSHI, KOICHI KITAMURA, SHOZO MURANISHI, HIT ...1977 Volume 25 Issue 11 Pages 3078-3080
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of various alcohols on the intramuscular absorption of water-soluble drug was studies using isonicotinamide as a model compound. It was found that linearity of the disappearance curves of the drug was maintained in the presence of the tested alcohols. The absorption inhibitory effect was also demonstrated when other alcohols of different classes were used, and it was increased with the increase of the molecular weight of the monohydric alcohols. Good correlations were demonstrated not only between the absorption inhibitory effect and denaturating power but also between the absorption inhibitory effect and the hemolytic effect of alcohols.View full abstractDownload PDF (438K) -
MOHAMED A. EL-DESSOUKY, MOHAMED S. EL-EZABY, AHMED S. SHAWALI1977 Volume 25 Issue 11 Pages 3081-3087
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinetics of the reactions of iron (III) with benzoylacetanilides have been studied by stopped flow technique in the pH range 1.0-2.0 in water-ethanol media. The effect of temperature on the reaction rate was also studies. A mechanism was proposed to account for the observed kinetic date. Rate constants for the reaction of Fe (III) with eight different benzoylacetanilides were correlated by Hammett equation, log kx=-0.51 δx-0.98.View full abstractDownload PDF (718K) -
YOSHIHISA OKAMOTO, TAKEO UEDA1977 Volume 25 Issue 11 Pages 3087-3089
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn acylation of 2-cyanomethylbenzimidazole (2), which has the NH and the active methylene group as active site, in acetone by the Schotten-Baumann method was carried out. The acylation occurred at the nitrogen of the imidazole ring when 2, itself, was used as a base. In these experiments, 2 was condensed with acetone to give 2-(1-cyano-2-methyl-1-propenyl) benzimidazole (4a) in the presence of trimethylamine as a base, however, 2 could not react with acetone in the presence of pyridine as a base.View full abstractDownload PDF (442K) -
MASASHI OKADA, TAKAKO ANJO1977 Volume 25 Issue 11 Pages 3090-3093
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPreparation of several ring A-modified cardenolides from digitoxigenin is presented. 3, 5-Seco-4-nor-cardenolides were prepared by oxidative cleavage of the ring A of the 3-oxo-Δ4-derivative with ruthenium tetroxide and 4-oxa-cardenolides were derived from the 3, 5-seco-4-nor-cardenolide. The structure-activity relationship in these ring A-modified cardenolides is discussed.View full abstractDownload PDF (594K) -
TOSHIO NAMBARA, SHIGEO IKEGAWA, TOSHIKO HIRAYAMA, HIROSHI HOSODA1977 Volume 25 Issue 11 Pages 3093-3096
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to clarify the stereochemistry of hydrogen transfer from C-4 to C-6 during enzymatic transformation of cholesterol into cholestenone, the title compounds stereospecifically labeled with deuterium have been synthesized as an authentic specimen. The stereospecific labeling at 6β was attained by trans-diaxial opening of the 5α, 6α-oxido ring with lithium aluminum deuteride. Oxidation with chromium trioxide followed by dehydration with p-toluenesulfonic acid provided 6β-d1-cholestenone (4a). In the similar fashion 6β-d1-cholestenone (4b) was prepared from 6β-d1-3α, 5-cyclo-5α-cholestan-6α-ol (6) by way of 6-d1-cholesteryl acetate (7).View full abstractDownload PDF (594K) -
NOBUTAKA FUJII, SUSUMU FUNAKOSHI, TAKASHI SASAKI, HARUAKI YAJIMA1977 Volume 25 Issue 11 Pages 3096-3098
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethanesulphonic acid cleaved the Z group from H-Lys (Z)-OH without concomitant formation of H-Lys (Bzl)-OH in the presence of the cation scavenger, anisole.View full abstractDownload PDF (453K) -
JUNYA OKADA, TAKUJI SEO, KINICHI IMAI1977 Volume 25 Issue 11 Pages 3099-3102
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn connection with our studies on anticoccidial agents, some 1-(4-chlorobenzylamino)-3-substituted guanidine tosylates (3) were prepared. The structure of the aminoguanidines was proven by autoxidation of 3 into the corresponding benzylideneaminoguanidine (5).View full abstractDownload PDF (489K) -
FAKHRELDIN S. GHAZY, TOSHIKIRO KIMURA, SHOZO MURANISHI, HITOSHI SEZAKI1977 Volume 25 Issue 11 Pages 3103-3106
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInvestigation of the effect of riboflavine photolysates on the intestinal absorption of drugs has been pursued. Absorption studies were done using in situ recirculation technique. In the presence of riboflavine photolysates the intestinal absorption of phenol red was found to be pH dependant. The colon and rectal absorption of phenol red was promoted by the presence of riboflavine photolysates. No detectable effect of riboflavine photolysates on the intestinal absorption of moderately and rapidly absorbed drugs could be seen. There was no significant effect on the release of intestinal protein, contrary to the surface active agents where they produce undesirable side effects. Riboflavine photolysates modified the membrane permeability by decreasing its resistance to the passage of drug molecules known to be absorbed with great difficulty.View full abstractDownload PDF (568K) -
MORIO FUKUHARA, EIGO TAKABATAKE1977 Volume 25 Issue 11 Pages 3107-3110
Published: November 25, 1977
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe activity of drug-metabolizing enzymes in hepatic microsomes of rats with inflammatory lesions was determined. In the Donryu-rats carrying carrageenin-induced granuloma, the cytochrome P-450 and b5 levels and the activity of aniline hydroxylase in hepatic microsomes were depressed markedly at day 6 after s. c. injection of carrageenin when the granuloma formation and exudate accumulation occur rapidly. However, at day 15 after carrageenin injection when the granuloma is in regression, the activity of these enzymes was decreased slightly but without significant differences.View full abstractDownload PDF (532K)