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Volume 28, Issue 1
Displaying 1-50 of 58 articles from this issue
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SHUJI KONDO, AKIRA KUCHIKI, KEIICHI YAMAMOTO, KOICHI AKIMOTO, KOUICHI ...1980 Volume 28 Issue 1 Pages 1-7
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe urinary metabolites of nifedipine in a dog were isolated and identified by chromatographic and spectrometric techniques. A new major metabolite, 2, 6-dimethyl-4-(2-nitrophenyl)-5-methoxycarbonylpyridine-3-carboxylic acid (M-I), was found in both dog and human urine. A highly sensitive and specific method is described for the determination of nifedipine, M-I, and a previously reported metabolite. The method for analysis of nifedipine is based on the oxidation of nifedipine to its pyridine analog, benzene extraction, and determination by electron-capture gas chromatography. The method for analysis of the metabolites is based on ethyl acetate extraction of the acidified specimen, derivatization of M-I to its methyl ester, and determination by electron-capture gas chromatography. Quantitative determination was possible down to 5 ng/ml of nifedipine using 1 ml samples of biological specimens. This method was used to measure plasma levels of nifedipine and its metabolites in dogs, and urinary excretion by humans after oral administration of a nifedipine preparation. It was found that nifedipine was absorbed, metabolized, and excreted rapidly, and that the main metabolite was M-I.View full abstractDownload PDF (736K) -
JUN OKUDA, NORIHIRO HORIGUCHI1980 Volume 28 Issue 1 Pages 8-13
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRiboflavin-5'-monobutyrate has the same vitamin B2 activity (nutritional and ariboflavinosis-curing effects) in rats as riboflavin, whereas the vitamin B2 activity of riboflavin-5'-monopalmitate was less than that of riboflavin or riboflavin-5'-monobutyrate.View full abstractDownload PDF (628K) -
AYAKO GOTO, REIKO SAKURA, FUMIO ENDO1980 Volume 28 Issue 1 Pages 14-22
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present investigation was undertaken to examine the effects of added sodium chloride on solubilized systems of sodium lauryl sulfate (SLS) micellar solutions solubilizing alkylparabens by gel filtration. The results showed that the addition of sodium chloride decreased the distribution coefficients of alkylparabens between the SLS micellar and aqueous phases. The factors causing the decrease of distribution coefficients were investigated. Activity coefficients of SLS and alkylparabens in mixed micelles were estimated on the basis of ideal solution theory. The activity coefficients suggested that the addition of sodium chloride hardly changed the SLS-alkylparaben interaction in the mixed micelles. The decrease in the surface area per SLS molecule in the micelles on addition of sodium chloride seems to be an important factor.View full abstractDownload PDF (845K) -
KIYOKO TAKAHASHI, YOSHIYUKI SEYAMA, SABURO YAMASHITA1980 Volume 28 Issue 1 Pages 23-29
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1. Synthetic substrates conventionally used can give either the esterase or peptidase activity of elastase separately, but simultaneous determination of both activities using one substrate has not previously been attempted. 2. In this work, the esterase and peptidase activities of elastase were determined simultaneously. Esterase activity can be expressed in terms of formation of Ala3 and peptidase activity can be expressed in terms of formation of Ala2 with Ala3OMe as the substrate : Ala3OMe is split into Ala3+MeOH by the esterase activity of elastase and into Ala2+Ala-OMe by the peptidase activity. 3. The present method differentiates the esterase or peptidase activities of other enzymes from those of elastase. Ala3OMe is split to Ala3, and then to Ala2+Ala in a stepwise manner by other proteases such as collagenase and pronase E. 4. Trypsin and chymotrypsin enhanced both the peptidase activity and esterase activity of elastase in parallel. 5. The substrate, suc Ala3NA has been used conventionally to determine elastase activity, and the results with suc Ala3NA and Ala3OMe showed a good correlation.View full abstractDownload PDF (660K) -
TERUO TANAKA, ATSUSUKE TERADA, TETSUO MIYADERA, RYUJI TACHIKAWA1980 Volume 28 Issue 1 Pages 30-34
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Piperidylacetohydrazides (I-III) were reacted with ethyl acetoacetate (EA), methyl tetrolate (MT), and ethyl phenylpropiolate (EP) with the aim of obtaining tricyclic heterocycles (IV). The desired compounds were produced when the following hydrazides and esters were heated under reflux in ethanol : II and EA, III and MT, II and EP. Interestingly, when 2-piperidylacetohydrazide (I) and its N'-phenyl derivative (III) were reacted with EA or MT and with EA, respectively, they afforded 3, 4-dimethylpyrano [2, 3-c]-pyrazol (6) ones (Va and Vb) with the expulsion of ethyl 2-piperidylacetate (VII). The mechanism of formation of Va and Vb is discussed.View full abstractDownload PDF (596K) -
SHIGEYUKI OGURI, HIDEKO ISHIHARA, SETSUZO TEJIMA1980 Volume 28 Issue 1 Pages 35-41
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe title branched trisaccharide (19) was prepared from benzyl 2-acetamido-4, 6-O-benzylidene-2-deoxy-α-D-glucopyranoside (1) by stepwise Koenigs-Knorr condensation followed by removal of the protecting groups. Benzyl 2-acetamido-3-O-(2, 3, 4-tri-O-acetyl-β-D-xylopyranosyl)-2-deoxy-α-D-glucopyranoside (4), prepared by coupling 1 with 2, 3, 4-tri-O-acetyl-α-D-xylopyranosyl bromide followed by debenzylidenation, is a key intermediate in this preparation. Removal of the benzyl and O-acetyl groups of 4 gave a crystalline 2-acetamido-2-deoxy-3-O-(β-D-xylopyranosyl)-α-D-glucopyranose. Preferential etherification and esterification of 4 were investigated. Selective benzylation of 4 afforded the 6-O-benzoate (15). Condensation of 15 with 2, 3, 4, 6-tetra-O-acetyl-α-D-galactopyranosyl bromide provided a crystalline, protected trisaccharide in 41% yield, from which 19 was obtained as a white powder after removal of the protecting groups. Purified β-galactosidase from jack bean did not act on the β-galactosidic linkage in 19.View full abstractDownload PDF (923K) -
KAZUYUKI KIZUKI, CHIAKI MORIWAKI, HIROSHI MORIYA1980 Volume 28 Issue 1 Pages 42-48
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe pseudoglobulin fraction obtained from heated plasma (60°, 1 hr) of various animals (PFHP) is widely used as a substrate in kininogenase activity assay. In the present investigation, however, kinin-converting activity was found in dog PFHP ; namely 100 μg of synthetic kallidin was completely converted to bradykinin within 1 hr on incubation with 300 mg of dog PFHP. The converting activity could be destroyed by further heating at 100° for 30 min. Kinin-converting activity was present in various species of PFHP's, though the activity of dog PFHP was the most potent among the PFHPs checked in this investigation. The kinin liberated from dog kininogen by guinea-pig coagulating gland kallikrein (CGK) was also identified by chromatographic analysis and by the DNS method. It has been reported that CGK liberates bradykinin from dog kininogen but it is now clear that CGK in fact liberates kallidin, like other glandular kallikreins, and that the kallidin is further converted to bradykinin by the contaminating kinin-converting enzyme in the substrate preparation.View full abstractDownload PDF (766K) -
SABURO NAKANO, TOMOHIKO YOSHIDA, HIROKAZU TANIGUCHI, MASANORI YASUKI1980 Volume 28 Issue 1 Pages 49-56
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHalogen derivatives of 2 (1H)-quinolinethione, alkyl derivatives of 1, 2-dihydro-2-thioxo-4-quinolinecarboxylic acid, and alkyl 1, 2-dihydro-2-thioxo-4-quinolinecarboxylate were synthesized. The detection limits for metal ions with these reagents were examined by spot tests. The metal ions which gave a precipitate with these reagents were the same as those reported previously. iso-Amyl 1, 2-dihydro-2-thioxo-4-quinolinecarboxylate (ATQ) forms a 1-to-1 compound with silver, and an ethanolic solution of ATQ was used as a titrant to determine 0.01-0.0001 M silver ions potentiometrically. The coefficient of variation was 1.8% (n=10) for 107.4 μg of silver. Silver protein was titrated potentiometrically with ATQ in 50% (v/v) ethanolic solution. The silver content was 8.0%, with a coefficient of variation of 1.8% (n=5).View full abstractDownload PDF (721K) -
KOSHI CHIKASAWA, MASAHIKO UYETA1980 Volume 28 Issue 1 Pages 57-61
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photolysis of monochlorobenzene by ultraviolet irradiation was investigated and found to yield monochlorinated biphenyls, biphenyl, and benzene. The amounts of these products increased with reaction time up to 20 hours. The yields of 2-, 3- and 4-chlorobiphenyl, biphenyl and benzene in monochlorobenzene were 708 ppm, 965 ppm, 1012 ppm, 226 ppm and 410 ppm, respectively, after 20 hours, but subsequent increases were relatively slow. One possibility is that monochlorinated biphenyls formed from monochlorobenzene are gradually decomposed by further irradiation. The photostability of monochlorinated biphenyls and biphenyl was in the order : biphenyl »4-chlorobiphenyl>3-chlorobiphenyl>2-chlorobiphenyl.View full abstractDownload PDF (564K) -
TAIICHIRO WATANABE, YOICHI KAWANO, TERUO TANAKA, TOSHIHIKO HASHIMOTO, ...1980 Volume 28 Issue 1 Pages 62-69
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESStert-Butyl (±)-7-amino-3-trifluoromethyl-3-cephem-4-carboxylate (16) and the 2-cephem derivative (21) were obtained by total synthesis starting from tert-butyl N-benzylideneglycinate (1). This synthesis is the first example of the reaction of the N-benzylideneglycinate anion with a reactive α-haloketone to give a β-hydroxy-γ-halo-α-aminoester (5a and 5b). The amino esters were treated with ethyl thioformate and then potassium carbonate, leading to the 4, 5-dihydro-6H-1, 3-thiazine derivatives (8a and 8b). After cycloaddition of 8a and 8b with azidoacetyl chloride and catalytic hydrogenation of the azido group, the resulting trans 7-aminocephem compound (12) was converted to the cis isomer (16) by the established method, involving reduction of the o-nitrobenzenesul-fenimino derivative (14).View full abstractDownload PDF (940K) -
YOICHI KAWANO, TAIICHIRO WATANABE, JUNICHI SAKAI, HIDETOSHI WATANABE, ...1980 Volume 28 Issue 1 Pages 70-79
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious acylamido derivatives of 3-trifluoromethyl-3-cephem-4-carboxylic acid were synthesized and tested for in vitro antibacterial activities. The 3-trifluoromethylcephalosporin derivatives synthesized herein are 7α- and 7β-acylamido-3-cephem-, 7α- methoxy-7β-acylamido-3-cephem- and 7β-acylamido-2-cephem-4-carboxylic acids. Among these compounds, the R-mandelamido derivative (IIIb) showed the highest antibacterial activity against gram-negative bacteria at pH 7.0. The minimum inhibitory concentration values of the 2-thienylacetamido- and phenylglycylamido derivatives are compared with those of the 3-methyl- and 3-chloro analogs, and structure-activity relationships are discussed.View full abstractDownload PDF (1153K) -
EIKO OHTSUKA, RYOICHI FUKUMOTO, MORIO IKEHARA1980 Volume 28 Issue 1 Pages 80-84
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA deoxyribohexanucleotide corresponding to a restriction endonuclease (Eco RI) recognition sequence, d-G-A-A-T-T-C, was synthesized by stepwise condensation of mononucleotides using dicyclohexylcarbodiimide (DCC) or 2, 4, 6-triisopropylbenzenesulfonyl chloride (TPS) as the condensing reagent. Protected oligonucleotides were separated by ion-exchange chromatography or gel filtration and the deblocked hexanucleotide was purified by DEAE-cellulose column chromatography in the presence of 7 M urea. The product was characterized by enzymatic hydrolysis and its temperature-absorption profile was measured at high ionic strength.View full abstractDownload PDF (834K) -
KIYOSHI EZUMI, TANEKAZU KUBOTA1980 Volume 28 Issue 1 Pages 85-91
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSince the partition coefficient P and the dissociation constant pKa are important in studies of structure-activity relationships, the pH dependence of the apparent partition coefficient Pa was quantitatively studied for the cases of acids and bases. Linear relations for mono-acids and mono-bases, but parabolic relations for the dissociation of two functional groups in the pH region studied were derived between Pa and proton concentration. The equations, however, are different for acids and bases. These equations make it possible to determine pKa and the log P simultaneously. Some experimental systems have been measured and compared with the results obtained by other techniques ; the agreement was good. A consideration of the dissociation in the organic phase showed that the correction factor due to ionic dissociation in the organic phase for an octanolbuffer system is negligible in the pH region near the pKa value, but is not negligible in the general equation connecting the Pa and P values.View full abstractDownload PDF (802K) -
MASAAKI UCHIDA, YUTAKA KOIKE, GENJIRO KUSANO, YOSHIKAZU KONDO, SHIGEO ...1980 Volume 28 Issue 1 Pages 92-102
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix sesquiterpene lactones (I-VI) were isolated and characterized as constituents of Chloranthus japonicus (Chloranthaceae). The lactones chloranthalactone A-E (I-V) were found to be lindenane derivatives, and the lactone VI was identified as atractylenolide III. The structure of chloranthalactone C (III) was determined by X-ray crystallographic analysis of a crystal of III in conjunction with the negative Cotton effect in the optical rotatory dispersion (ORD) curve and negative circular dichroism curve of the ketoalcohol (XII) prepared from III. The stereostructures of chloranthalactone A and B (I and II) were deduced from the ORD curves of the degradation products (VII and X). The cytotoxicities of these lactones against mouse lymphosarcoma L-5178Y cells were determined in comparison with that of helenalin, and they were found to show moderate cytotoxic effects.View full abstractDownload PDF (1229K) -
SOJI SUGAI, KAZUO TOMITA1980 Volume 28 Issue 1 Pages 103-109
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel pyrolysis reactions of 4-isoxazolin-3-thiones (X) are described, affording two regioisomeric 1, 4-dithiins (III, IV) and thioacetamides (XI). Among the thioacetamides, N-methylbenzoylthioacetamide (XIe) was identical with an authentic sample prepared by the reduction of 2-methyl-5-phenyl-4-isoxazolin-3-thione (Xe) with thiophenol. The structures of the dithiins were deduced from the physicochemical data, especially the shielding and deshielding effects in the NMR spectra. A mechanism for the reactions is proposed by analogy with the thermal isomerization of 3-isoxazolones into 2-oxazolones. In order to account for the formation of the isomeric dithiins, a thiirene intermediate (II) was assumed to be involved in the reaction pathway.View full abstractDownload PDF (676K) -
TADATOSHI YAMAGUCHI, MASAZUMI WATANABE, TANEZO TAGUCHI, MASAHARU KOJIM ...1980 Volume 28 Issue 1 Pages 110-114
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 5, 6-dimethanesulfonyl derivative (2) of methyl 2, 3-di-S-benzyl-2, 3-dideoxy-2, 3-dithio-α-D-altrofuranoside (1) reacted with sodium ethyl xanthate to give methyl 2, 3-di-S-benzyl-2, 3, 5, 6-tetradeoxy-2, 3-dithio-5, 6-(thiocarbonyl) dithio-β-L-galactofuranoside (3) and -α-D-altrofuranoside (4). Reduction of 3 and 4 with liquid ammonia-metallic sodium gave methyl 2, 3, 5, 6-tetradeoxy-2, 3, 5, 6-tetrathio-β-L-galactofuranoside (5) and -α-D-altrofuranoside (6), respectively.View full abstractDownload PDF (677K) -
NOBUYUKI YAMAJI, KYOKO TAHARA, MOTOHIKO KATO1980 Volume 28 Issue 1 Pages 115-119
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of 2-mercapto-1, N6-etheno c-AMP (c-AMP : adenosine 3', 5'-cyclic phosphate) (V) and 2-mercapto c-AMP (III) with hydrogen peroxide afforded 2-sulfo-1, N6-etheno c-AMP (VIII) and 2-sulfo c-AMP (IX), respectively. Deblocking of the etheno residue of VIII afforded IX. Potassium cyanide reacted with 2-bromo-1, N6-etheno c-AMP (VI) in dimethylformamide (DMF) at room temperature to yield 2-cyano-1, N6-etheno c-AMP (X), which was isolated by Dowex 50-X8 (H+) column chromatography. Compound (X) was hydrolyzed to 2-carbamoyl-1, N6-etheno c-AMP (XI), then to 2-carboxy-1, N6-etheno c-AMP (XII) by aqueous sodium hydroxide. Compound XII was converted to 1, N6-etheno c-AMP (IV) by heating in dimethylsulfoxide (DMSO). Deblocking of the etheno residue of XI and XII afforded 2-carbamoyl c-AMP (XIII) and 2-carboxy c-AMP (XIV), respectively. Compound XIII was hydrolyzed by aqueous sodium hydroxide to yield XIV.View full abstractDownload PDF (646K) -
EIKO OHTSUKA, TOSHIKI TANAKA, MORIO IKEHARA1980 Volume 28 Issue 1 Pages 120-125
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA hexanucleotide pC-A-A-C-C-Ap, which corresponds to the 3'-end of tRNAfMet, was synthesized as a bisphosphorylated form, which should be a suitable donor substrate for joining with RNA ligase. 3'-Phosphorylated oligonucleotides were condensed by a triester method and the 5'-terminus of the protected hexanucleotide was phosphorylated with dianilidophosphorochloridate after demonomethoxytritylation. A site-directed base transition mutant sequence C-G-A-C-C-Ap was also synthesized by the triester method using suitably protected 3'-phosphorylated oligonucleotides.View full abstractDownload PDF (655K) -
MAKOTO UCHINO, MINORU SEKIYA1980 Volume 28 Issue 1 Pages 126-133
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlkyl and aryl phthalimidomethyl sulfides give alkane- and arenesulfenyl chlorides on reaction with equimolar sulfuryl chloride or molecular chlorine in an aprotic solvent at room temperature, but give alkane- and arenesulfinyl chlorides on reaction with two molar equivalents of the same reagent in the presence of acetic anhydride under the same conditions. The utility of these reactions for the synthesis of organo sulfenyl chlorides and sulfinyl chlorides was confirmed.View full abstractDownload PDF (723K) -
MITSURU FURUKAWA, TADASHI OHKAWARA, YOSHIHIDE NOGUCHI, MASUMI NISHIKAW ...1980 Volume 28 Issue 1 Pages 134-141
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConvenient one-step syntheses of sulfinamides and sulfinate esters from sulfinic acids were achieved by using coupling reagents, such as 2-chloro-1-methylpyridinium iodide, γ-saccharine chloride, N, N'-dicyclohexylcarbodiimide, and diethyl azodicarboxylate and triphenylphosphine. Ammonolysis of sulfinate esters also gave sulfinamides.View full abstractDownload PDF (815K) -
SADAO NISHIGAKI, JUNKO SATO, KIYOKO SHIMIZU, KIYOKO FURUKAWA, KEITARO ...1980 Volume 28 Issue 1 Pages 142-149
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHeating of 6-arylamino-1, 3-dimethyluracils (IIa-e) with one-carbon reagents (dimethylformamide dimethylacetal, dimethylformamide-phosphorus oxychloride, and triethyl orthoformate) afforded 1, 3-dimethylpyrimido [4, 5-b] quinoline-2, 4 (1H, 3H)-diones (Va-e) via the intramolecular cycloaddition of azahexatrienes. Similarly, treatment of IIa with arylaldehydes provided 5-aryl-1, 3-dimethylpyrimido [4, 5-b] quinoline-2, 4 (1H, 3H, 5H, 10H)-diones (VIIa-e), which were subsequently dehydrogenated with either thionyl chloride or diethyl azodicarboxylate to give 5-aryl-1, 3-dimethylpyrimido [4, 5-b] quinoline-2, 4 (1H, 3H)-diones (Xa-e). The reaction of 6-arylamino-1, 3-dimethyl-4-N-phenylcytosines (XIIa-c) with dimethylformamide dimethylacetal to give 4-arylimino-1, 3-dimethylpyrimido [4, 5-b] quinoline-2 (1H, 3H)-ones (XIIIa-c) is also described.View full abstractDownload PDF (718K) -
AKIRA YAMANE, AKIRA MATSUDA, TOHRU UEDA1980 Volume 28 Issue 1 Pages 150-156
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 6-methylsulfonyl-9-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl) purine with ethyl acetoacetate and sodium hydride in tetrahydrofuran afforded, after deblocking, 6-ethoxycarbonylmethyl-9-β-D-ribofuranosylpurine. Similarly, replacement of the 6-methylsulfonyl moiety with other carbanions derived from diethyl malonate, ethyl cyanoacetate, malononitrile, nitromethane, and sodium cyanide gave the corresponding 6-C-substituted purine nucleosides. Most of these derivatives exist as the 6-(1H)-exomethylene tautomeric forms. 6-Ethoxycarbonylmethylpurine riboside was further converted to 6-methyl, ethyl, propyl, butyl, and pentyl-purine ribosides by decarboxylation or prior alkylation of the methylene group followed by de-carboxylation. This reaction sequence facilitated the preparation of hitherto almost inaccessible alkyl or C-substituted purine nucleosides.View full abstractDownload PDF (827K) -
AKIRA YAMANE, HIDEO INOUE, TOHRU UEDA1980 Volume 28 Issue 1 Pages 157-162
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 4-thiouridine with phenacyl bromide, bromoacetone, and ethyl bromoacetate gave the corresponding 4-thioalkylcarbonyl derivatives. The sulfur extrusion reactions of these compounds afforded ribosides of 4-phenacylidene-2 (3H)-pyrimidinone, 4-acetonylidene-2 (3H)-pyrimidinone, and 2-pyrimidinone-4-acetic ester, respectively. The ease of sulfur extrusion depends on the electron-withdrawing ability of the carbonyl group attached to the 4-S-methylene group. Sulfur extrusion reactions starting from 6-thioinosine similarly gave the ribofuranosides of 6-phenacylpurine and 6-acetonylpurine. These purine ribosides exist meinly as the enol form rather than the keto form.View full abstractDownload PDF (779K) -
SEIICHI SAKUMA, SACHIKO KAWANISHI, JUNZO SHOJI1980 Volume 28 Issue 1 Pages 163-168
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGlycoside H2, C56H92O25, [α]D -25.9°(MeOH), which causes marked potentiation of the effect of NGF (nerve growth factor), was isolated from Bei-Wujiapi (the cortex of Periploca sepium BGE., Asclepiadaceae) and its chemical structure was established to be ⊿5-pregnene-3β, 16α, 20α-triol 3-O-[2-O-acetyl-β-D-digitalopyranosyl (1→4)-β-D-cymaro-pyranoside] 20-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl (1→2)-β-D-digitalopyranoside] (1).View full abstractDownload PDF (814K) -
YOSHIYA YAMAHIRA, TETSUO NOGUCHI, TAKESHI NOGUCHI, HIROSHI TAKENAKA, T ...1980 Volume 28 Issue 1 Pages 169-176
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism of the uniformity of diazepam absorption rate from medium chain triglyceride (MCT) solution was investigated in comparison with the absorption from an aqueous suspension. The metabolism of MCT in the stomach was examined in vitro using the enzyme extract of the rat stomach. The content of a metabolite, medium chain monoglyceride (MCM), increased up to 1.5% at pH 3.6 during incubation for 30 min. Experiments using a newly devised gastric emptying simulator suggested that improved dispersibility of MCT solution, by virtue of the formed MCM, resulted in the uniform gastric emptying rate (GER) of this preparation. In the case of diazepam aqueous suspension, both GER and the gastric absorption rate of the drug seemed to be significant factors in the variable absorption rate of diazepam, though GER was considered to be the major factor. In experiments with the gastric emptying simulator, the GER of the aqueous suspension seemed more variable than that of the MCT solution containing MCM. Consequently, the apparent uniform absorption rate of diazepam-MCT preparation is considered to be attributable to the relatively uniform GER of the MCT digestion mixture which is formed in the stomach.View full abstractDownload PDF (818K) -
KOTARO TAKAHASHI, MASAKO TAKANI1980 Volume 28 Issue 1 Pages 177-180
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe alkaline degradation product of usnic acid was identified as 4, 6-dihydroxy-3, 5-dimethylcoumaran-2-one on the basis of spectral and chemical evidence. The reaction mechanism is discussed.View full abstractDownload PDF (482K) -
JUN OKUDA, NORIHIRO HORIGUCHI1980 Volume 28 Issue 1 Pages 181-188
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRiboflavin-5'-monobutyrate (R-MB, mp 244-245°) was synthesized from riboflavin and butyric anhydride (yield : 10%) as well as from riboflavin-2', 3', 4', 5'-tetrabutyrate and hydrazine hydrate (yield : 44%). Riboflavin-5'-monopalmitate (R-MP, mp 228-230°) was also prepared from riboflavin and palmitic anhydride (yield : 9.8%). The absorption, fluorescence, and infrared spectra, and Rf values of R-MB and R-MP are given. R-MP was hardly hydrolyzed by pure hog hepatic carboxylesterase. However, R-MB was readily hydrolyzed to riboflavin by pure hog hepatic carboxylesterase, though not by pure pancreatic lipase (triacylglycerol lipase), acetylcholinesterase, or cholinesterase. The activity of carboxylesterase could therefore be estimated by fluorometric determination of riboflavin hydrolyzed from R-MB. The optimum incubation conditions for the assay of carboxylesterase with R-MB were pH 7, 37°, 15 min. Studies on the rat organs and liver subcellular distributions of carboxylesterase showed that the enzyme is localized in the small intestine, kidneys, lungs, heart, and blood, and high carboxylesterase activity was demonstrated in the microsomal fraction in rat liver. R-MB was a rather specific substrate for carboxylesterase, permitting selective assay of this enzyme activity.View full abstractDownload PDF (827K) -
MORIO IKEHARA, SEIICHI UESUGI, TOSHIO SHIDA1980 Volume 28 Issue 1 Pages 189-197
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo sequence isomers of dinucleoside monophosphates, 8, 2'-anhydro-8-thio-9-β-D-arabinofuranosyladenylyl-(3'-5')-6, 2'-anhydro-6-oxy-1-β-D-arabinofuranosyluracil (AspU°) (III) and 6, 2'-anhydro-6-oxy-1-β-D-arabinofuranosyluridylyl-(3'-5')-8, 2'-anhydro-8-thio-9-β-D-arabinofuranosyladenine (U°pAs) (IV), were synthesized by condensation of suitably protected nucleoside and nucleotide units using dicyclohexyl carbodiimide as a condensing reagent. Examination of the UV, CD and NMR spectra of these dimers led us to the conclusion that, whereas compound III did not take a stacked conformation, compound IV took a well-stacked conformation, in which the bases were stacked along a left-handed screw axis. The adoption of this conformation could be interpreted in terms of the high base torsion angles in both nucleoside units.View full abstractDownload PDF (886K) -
TERUOMI JOJIMA, HIDEO TAKESHIBA, TAKAO KINOTO1980 Volume 28 Issue 1 Pages 198-201
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIntramolecular cycloaddition of 3-chloro-6-(2-allyloxyphenoxy) pyridazines yielded various hydroxyxanthenes, which were also prepared by similar cycloaddition of 3-substituted-6-(2-allylphenoxy) pyridazines containing methoxy groups on their benzene rings, followed by demethylation of the resulting methoxyxanthenes. The mechanism of the reaction is discussed.View full abstractDownload PDF (508K) -
TAKAO SAKAMOTO, TAKAYASU ONO, TAKEJI SAKASAI, HIROSHI YAMANAKA1980 Volume 28 Issue 1 Pages 202-207
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 2, 6-disubstituted pyrimidines with acyl radicals generated either from pyruvic acid-AgNO3-(NH4)2S2O8 (method A) or from aldehyde-FeSO4-t-BuOOH (method B) in aq. H2SO4, gave the corresponding 2, 6-disubstituted 4-acylpyrimidines. However, 4, 6-disubstituted pyrimidines gave 2-acetyl-and 2, 5-diacetyl-4, 6-disubstituted pyrimidines under the same conditions (methods A and B). Similarly, homolytic amidation of pyrimidines in which the 2- or 4-positions are free yielded pyrimidine-2- or -4-carboxamides.View full abstractDownload PDF (674K) -
KIMIHIRO YOSHIMOTO, YOSHITAKA ITATANI, KANOKO SHIBATA, YOSHISUKE TSUDA1980 Volume 28 Issue 1 Pages 208-219
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAll the isomers of the mono-O-myristoyl derivative of methyl α- and β-D-glucopyranosides were unambiguously prepared, and their 1H- and 13C-NMR spectra are discussed in relation to the stereochemistry of the pyranose ring and ester grouping. The acylation shifts on introducing a myristoyl group at each carbon atom of the pyranose ring in the acyl derivatives were tabulated and were shown to be additive parameters for diacyl derivatives. A diacyl mixture obtained by direct acylationof methyl β-D-glucopyranoside could be completely analyzed by 13C-NMR. The effects of orientational differences of an anomeric methoxyl group on pyranose carbon shielding were also clarified in every mono-O-myristoyl-D-glucopyranoside. An anomalous effect at C2 of the 2-O-acyl derivative is suggested to originate from a conformational change of the ester group in the β-anomer.View full abstractDownload PDF (1277K) -
HIROKI TAKAHATA, MINORU ISHIKURA, TAKAO YAMAZAKI1980 Volume 28 Issue 1 Pages 220-226
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnnulation reactions of methyl valelolactim (2) and methyl caprolactim (3) with cyclic β-aminoesters, such as 2-carbethoxymethyl piperidine derivatives (4 or 5), often gave two kinds of products apparently arising from the imine and enamine forms of 2 and 3. These chemical properties were consistent with NMR observations of lactim ethers in CD3OD solution.View full abstractDownload PDF (700K) -
EIICHI KITAZAWA, AIYA SATO, SHUJI TAKAHASHI, HARUMITSU KUWANO, AKIRA O ...1980 Volume 28 Issue 1 Pages 227-234
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive novel furanoditerpenes of the ent-clerodane type, plaunol A (1), B (2), C (3), D (4) and E (5), were isolated from a fraction of Croton sublyratus KURZ extract with potent anti-Shay ulcer activity. Their absolute structures were determined from the spectral data and by chemical correlations.View full abstractDownload PDF (904K) -
NORIO SUZUKI, YOSHIAKI TANAKA, RENZO DOHMORI1980 Volume 28 Issue 1 Pages 235-244
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of a search for new antimicrobial agents, some 3, 5-disubstituted 5, 8-dihydro-8-oxoimidazo and triazolo [4, 5-b] [1, 8] naphthyridine-7-carboxylic acids and related compounds, which contain a new ring system, were prepared. The reactions of 6-amino-7-alkylamino-1-ethyl-1, 4-dihydro-4-oxo-1, 8-naphthyridine derivatives (3, 7, 11, 12 and 35) with acid, acetic anhydride, ethyl orthoformate and ethylxanthate afforded several imidazo [4, 5-b] [1, 8] naphthyridine derivatives. Treatment of the diamines (11 and 12) with sodium nitrite gave the triazolo [4, 5-b] [1, 8] naphthyridine derivatives (15 and 16). Reaction of the 7-acetylamino-4-hydroxy-1, 8-naphthyridine-3-carboxylate (17) with 1, 2-bromochloroethane gave different products (24 and 27), depending upon the reaction conditions. 3-Methyl-5-vinyl-5, 8-dihydro-8-oxoimidazo [4, 5-b] [1, 8]naphthyridine-7-carboxylic acid (38) was prepared by successive chloroethylation, nitration, chlorination, substitution with methylamine, reduction of the nitro group, imidazole cyclization and elimination of hydrogen chloride with simultaneous hydrolysis of the ester group. Some compounds obtained in this work showed activity nearly equal to that of pipemidic acid, but were slightly less active against Ps. aeruginosa.View full abstractDownload PDF (1135K) -
MIKIO YAMAZAKI, HARUHIRO FUJIMOTO, TAKAO KAWASAKI1980 Volume 28 Issue 1 Pages 245-254
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new indolic metabolites, fumitremorgin A and B, were isolated from the fungus Aspergillus fumigatus. These two metabolites caused severe tremor and convulsion in experimental animals. The structure of fumitremorgin A, including the stereochemistry, was determined to be 1 mainly on the basis of the spectral data for the compound and some derivatives obtained from it. The stereochemical factors affecting the appearance of tremorogenic activity in fumitremorgin A and related compounds are discussed.View full abstractDownload PDF (1036K) -
TAKEO HIGASHINO, TATSUHIKO KATORI, SHIZUO YOSHIDA, EISAKU HAYASHI1980 Volume 28 Issue 1 Pages 255-261
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNucleophilic reagents were found to react with 3-phenyl-3H-1, 2, 3-triazolo [4, 5-d]-pyrimidine-7-carbonitrile (1) in two ways, depending on the nature of the reagent. One is substitution by attack of the reagent of the carbon at the 7-position, to which the cyano group is bonded. The other is addition to the cyano group by attack of the reagent at the carbon of the cyano group. The substitution reaction occurs with amines, alkoxide ions, carbanions (active methylene compounds or ketones in the presence of sodium hydride), and the Grignard reagents, resulting in the formation of 4-alkylamino-(2), 4-alkoxy-(3), 4-substituted (4), and 4-alkyl-3-phenyl-3H-1, 2, 3-triazolo [4, 5-d] pyrimidines (5), respectively. The addition reaction occurs in the reactions with 98% sulfuric acid and with hydroxylamine, resulting in the formation of amide (6a) and amidoxime (7), respectively. The amide (6a) forms esters (8) with alcohols, in the presence of acid. The ethyl ester (8b) is hydrolyzed by ethanolic potassium hydroxide to give the acid (9). Moreover, 8b reacts with amines, hydroxylamine, and hydrazines to form amides (6b and 6c), hydroxamic acid (10), and hydrazides (11a and 11b), respectively.View full abstractDownload PDF (772K) -
YOSHIRO KOBAYASHI, TAKEO TAGUCHI, TSUTOMU MORIKAWA, ETSUKO TOKUNO, SHO ...1980 Volume 28 Issue 1 Pages 262-267
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxidative coupling of ketone enolates and trimethylsilyl enol ethers by means of cupric trifluoromethanesulfonate [Cu(OTf)2] is described in detail. 1, 4-Diketones were effectively prepared by treating lithium enolates with Cu(OTf)2 in i-PrCN. 1, 3-Cyclopentanedione derivatives were synthesized through intramolecular coupling of 2, 4-pentanedione derivatives. Treatment of trimethylsilyl enol ethers with Cu(OTf)2 in i-PrCN also afforded the corresponding coupling products.View full abstractDownload PDF (637K) -
TAEKO KAWAMURA, NAOMI YAGI, HIROMI SUGAWARA, KAZUTAMA YAMAHATA, MASAHI ...1980 Volume 28 Issue 1 Pages 268-276
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe binding of sulfamethoxazole and sulfaphenazole to the plasma protein of 7 patients with chronic renal failure, undergoing chronic hemodialysis, was studied by the equilibrium dialysis method and the results were compared with those for 12 normal subjects. The binding percentages of the two sulfonamides were found to be impared in the patients'plasma as compared with normal plasma. The binding percentages increased in the patients'plasma after hemodialysis except in the cases of 2 patients for sulfamethoxazole (SMX) and 1 patient for sulfaphenanzole (SPH). The effect of hemodialysis on drug protein binding was examined by calculating the percentage displacement of bound sulfonamides by oxyphenbutazone and sulfinpyrazone. Percentage displacements were higher in the patients' plasma than in normal plasma. The percentage displacement decreased in the patients'plasma after hemodialysis, except in the cases of 1 patient for SMX and 1 patient for SPH. Such a decrease in the percentage displacement after hemodialysis suggests that the drug binding activity of plasma albumin can be improved through hemodialysis for patients with chronic renal failure.View full abstractDownload PDF (845K) -
TAKESHI KAWAMATA, SEIICHI INAYAMA, KAZUKO SATA1980 Volume 28 Issue 1 Pages 277-281
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new approach to the synthesis of ⊿α, β-butenolides from γ-butanolides by means of the electrolytic oxidation of α-carboxy-α, γ-dimethyl-γ-butyrolactone (3b) and its α-carboxy-α-methyl analog (3d) resulted in predominant formation of the endocyclic ⊿α, β-isomers, α-methyl-⊿α, β-γ-valerolactone (5a) and α-methyl-⊿α, β-γ-butenolide (5c), accompanied by the exocyclic ⊿α, β-isomers, α-methylene-γ-valerolactone (5b) and α-methylene-γ-butanolide (5d), respectively, under various conditions. The conventional oxidation of α-phenylseleno- (4a) and α-phenylthio-α-methyl-γ-valerolactone (4b) was found to yield a mixture of 5a and 5b. The regiospecific preparation of the endo-isomer (5a) was ultimately achieved by the use of sequential reactions reported earlier, starting from α-methyl-γ-valerolactone (1a) via α-methoxycarbonyl- (3a), α-carboxy- (3b), and α-bromo-α-methyl-γ-valerolactone (3c).View full abstractDownload PDF (678K) -
by Oxidation of α-Dimethylamino-α-methylbutanolides in a Fused Lactone SystemSEIICHI INAYAMA, TAKESHI KAWAMATA, NOBUKO SHIMIZU1980 Volume 28 Issue 1 Pages 282-287
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew methods have been developed for the preparation of α-methylene-γ-butyrolactones (exo-type olefin) and α-methyl-⊿α, β-butenolides (endo-type olefin) starting from an α-carboxy-α-methyl-γ-butyrolactone in a fused lactone system, e. g., (+)-11β-carboxy-(2a) and (+)-11α-carboxy-3α, 4β, 5α, 6βH-hexahydrosantonin (2c). The method for exocyclic (⊿α, β') butenolides, e. g., ⊿11(13)-dehydrohexahydrosantonin (5a), consists of the oxidative syn elimination of an 11β-oriented α-dimethylaminolactone (4b) derived smoothly with retention of the configuration of the α-substituent through several intermediates, starting from an α-carboxy-α-methylbutanolide, e. g., 11β-carboxy-3α, 4β, 5α, 6βH-hexahydrosantonin (2a) (11β-COOH/7α-H : trans). The method for endo-type butenolides, e. g., ⊿7(11)-dehydrohexahydrosantonin (8a), consists of electrolytic oxidation of the trans- or cis-carboxylactone acid, e. g., 11β-carboxy-(2a) and 11α-carboxy-3α, 4β, 5α, 6βH-hexahydrosantonin (2c) (11α-COOH/7α-H : cis), irrespective of the configuration of the α-carboxyl group in the santanolide.View full abstractDownload PDF (810K) -
SEIICHI INAYAMA, TAKESHI KAWAMATA, TADAAKI HIROSE1980 Volume 28 Issue 1 Pages 288-295
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple and stereoselective preparation of (-)-11β-carboxysantonin (8a) was achieved by carboxylation of l-α-santonin (5b), based on the non-stereoselective two-step method described earlier. (+)-11β-Carboxy-(3α) and (+)-11α-carboxy-3α, 4β, 5α, 6βH-hexahydrosantonin (3b) were prepared in a ratio of 3 : 1 by alkoxycarbonylation of 3α, 4β, 5α, 6β, 11βH-hexahydrosantonin (HHS) (1a), followed by hydrolysis. The absolute configurations at C-11 in the three optically active 11-carboxysantonins have now been confirmed on the basis of the stereochemistry of the fourth new stereoisomer, (-)-11β-carboxysantonin (8a). The complete structure of 8a was established by its transformation to (+)-11β-carboxy-4β, 5α, 6βH-tetrahydrosantonin (7a), correlating with 3a. The proton magnetic resonance (PMR) signals of 6β-hydrogens in 11β-carboxy- or 11β-methoxycarbonyl-HHS (2a-4a) are anisotropically shifted further downfield compared to those in the 11α-oriented epimers (2b-4b). A similar result was obtained for the pairs of epimers in the 4β, 5α, 6β, 11βH-tetrahydrosantonin (THS) series (6a, 7a and 6b, 7b). The stereospecific decarboxylation of the 11β- and 11α-carboxylactone derivatives (3a, 7a, 8a, and 3b, 7b, 8b) afforded the thermodynamically more stable 11α-methyl lactone analogs (1a, 5a, 5b), and not the 11β-methyl epimers (1c, 5c, 5d). The rate of decarboxylation of the former lactone acids was faster than that of the latter, supporting the foregoing assignments, based on spectral data, for the configurations of the 11β- and 11α-carboxyl groups.View full abstractDownload PDF (1020K) -
ISAO KITAGAWA, MASAYUKI YOSHIKAWA, KATSUYA KOBAYASHI, YASUHIRO IMAKURA ...1980 Volume 28 Issue 1 Pages 296-300
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe branching positions in the glucuronide moieties of desacyl-jegosaponin (1), desacyl-boninsaponin A (2), and sakuraso-saponin (3) have been reinvestigated. It has been found that the branching positions in the glucuronide moieties of these glucuronide saponins should be revised to C-2 and C-3 from the previously assigned C-2 and C-4.View full abstractDownload PDF (647K) -
MITSUYA TANAKA, SHIGEHISA KYOSAKA, SANAE YAMASHIRO1980 Volume 28 Issue 1 Pages 301-304
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe molecular weights and subunit compositions of bovine liver β-acetylhexosaminidase A (Hex) and B (Hex B) were studied using enzyme preparations purified by octyl Sepharose chromatography. Analysis by gel filtration showed that Hex A had a molecular weight of ca. 310000 (hexamer) at pH 5, 6, and 6.5, and was dissociated into dimers at pH 7 and 8, while the molecular weight of Hex B, ca. 310000, remained constant in the pH range of 5-8. The molecular weights of Hex A and B subunits as determined by electrophoresis in sodium dodecyl sulfate were both ca. 52000, and this value remained unaltered when the enzyme was treated with a reducing agent or denaturant.View full abstractDownload PDF (482K) -
KEIKO NAKAO, SHOHEI KAGAWA, KEIKO MURAKOSO, MITSUO HATA, AKIRA MATSUOK ...1980 Volume 28 Issue 1 Pages 305-310
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple radioreceptor assay for insulin was established with sensitivity sufficient to detect 10 μU/ml of insulin in human sera. This radioreceptor assay was carried out at 0° using rabbit erythrocyte membranes. The binding assay for the standard curve was performed in the presence of insulin-free serum, since the binding of insulin was greatly reduced by the addition of serum. Under the conditions used, 38% of the initial binding of 125I-insulin was displaced by 250μU/ml of native insulin. The sensitivity of the radioreceptor assay was dependent on the concentrations of both membrane protein and 125I-insulin. The ratio of IRI to insulin values obtained by the present assay was 0.93±0.10 for 19 healthy and diabetic subjects.View full abstractDownload PDF (652K) -
YOSHIO OKADA, YUKO TSUKA, MASAMI YAGYU1980 Volume 28 Issue 1 Pages 310-313
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBradykinin fragments and their analogs, Gly-X-Ser-Pro (X : L-Phe I, D-Phe II, L-Ala III, D-Ala IV, β-Ala V and Gly VI) and X-Ser-Pro (X : L-Phe VII and D-Phe VIII) were synthesized. Compounds I, II, V, VII and VIII prolonged the pentobarbital-induced sleeping time in mice at the dosage of 2.5 nmol per mouse.View full abstractDownload PDF (480K) -
TSUYOSHI TANIMOTO, TAKAO HAYAKAWA, JIRO KAWAMURA1980 Volume 28 Issue 1 Pages 314-318
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS20β-Hydroxysteroid dehydrogenase from Streptomyces hydrogenans is partially inactivated in sodium phosphate buffer within a short time. Inactivation of the enzyme was accelerated at acidic pH, and the enzyme was also inactivated by incubation with rose bengal. The inactivation due to acidic pH and rose bengal was prevented by glycerol ; 20% glycerol completely restored the activity lost at pH 5.5. The mechanism of stabilization of the enzyme by glycerol is not yet clear.View full abstractDownload PDF (568K) -
KYOKO KOIZUMI, HIROKO MIKI, YOKO KUBOTA1980 Volume 28 Issue 1 Pages 319-322
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 50% effective doses of five barbiturate-β-cyclodextrin complexes on oral administration to mice were compared with those of the corresponding barbiturates. In all cases tested, the complex gave a smaller ED50 than the intact drug. ED50 of phenobarbital, which forms the most stable complex and consequently shows the greatest enhancement in solubility, was reduced most markedly by complexation. With the exception of barbital, sleeping lag (the time from oral administration to loss of righting reflex) on administration of the complex to mice was shorter than that on giving an equimolar amount of the intact drug (p<0.001), and sleeping time (the time from loss to recovery of righting reflex) was significantly increased by inclusion complexation with β-cyclodextrin.View full abstractDownload PDF (490K) -
SHOZO MIYAZAKI, TOMOHIRO YAMAHIRA, HITOMI INOUE, TANEKAZU NADAI1980 Volume 28 Issue 1 Pages 323-326
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of endogenous bile on the intestinal absorption of indomethacin and phenylbutazone was investigated in control rats and in bile fistula rats. Oral administration of both drugs in suspension gave lower plasma concentrations in bile fistula rats than in control animals. On the other hand, studies in which solutions of the two drugs were administered intraduodenally to control and bile fistula rats indicated that bile had no effect on their plasma levels. These results suggest that bile plays an important role in the dissolution step in the absorption processes of indomethacin and phenylbutazone.View full abstractDownload PDF (534K) -
TETSUZO KATO, TAKUO CHIBA, SUSUMU TSUCHIYA1980 Volume 28 Issue 1 Pages 327-330
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photoreactions of diketene with maleic anhydride (4) and dimethylmaleic anhydride (6) gave 2-oxo-1-oxaspiro [3.3] heptane-cis-5, 6-dicarboxylic anhydride (5a, b) and 5, 6-dimethyl-2-oxo-1-oxaspiro [3.3] heptane-cis-5, 6-dicarboxylic anhydride (7a, b), respectively. Treatment of compounds 5 and 7 with hydrogen chloride in ethanol and methanol afforded the corresponding dialkyl 5-alkoxycarbonyl-3-oxoheptanedioate derivatives (8 and 10) and (9 and 11), respectively.View full abstractDownload PDF (562K) -
KATSUMI TABEI, ETSUKO KAWASHIMA, TETSUZO KATO1980 Volume 28 Issue 1 Pages 330-336
Published: January 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 5-hydroxy-2-phenyltetrahydro-2H-1, 2-oxazin-3-one derivatives (2) with thionyl chloride in the presence of pyridine afforded a mixture of stereoisomers of bis (3-oxo-2-phenyltetrahydro-2H-1, 2-oxazine-5-yl) sulfite derivatives (3) in total yields of 75-83%. On high-performance liquid chromatography, two meso-diastereoisomers (3-I and 3-II) and a racemic compound (3-III) were isolated.View full abstractDownload PDF (583K)