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Volume 34, Issue 7
Displaying 1-50 of 57 articles from this issue
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KOICHIRO MIYAJIMA, KEIKO TOMITA, MASAYUKI NAKAGAKI1986 Volume 34 Issue 7 Pages 2689-2697
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe cryoprotective activities of saccharides on liposome dispersion prepared from a mixture of egg yolk lecithin and dicetylphosphate (10 : 1 in molar ratio) were investigated in terms of the leakage of the entrapped marker (calcerin), and the changes of the turbidity and the half band-width of CH2 signals in the 1H-NMR spectrum. In the presence of more than 100 mM D-glucose in both the inner and outer aqueous phases of liposomes (concentration of phospholipid; 6.4mM), the liposome dispersion was stable to freezing at -70°C. D-Galactose, D-mannose, maltose and maltotriose showed similar activities to D-glucose. However, maltopentaose and DextranT-100 had no cryoprotective effect on the liposome dispersion. Sodium chloride, potassium chloride and urea also showed cryoprotective activities above their eutectic temperatures. The mechanism of the cryoprotective action of saccharides on the freezing of liposomes is discussed in terms of differential scanning calorimetry data and Raman spectra of aqueous saccharide solutions at low temperature.View full abstractDownload PDF (789K) -
HIROSHI KISHIMOTO, TAKAO IWASAKI, MASAKATSU YONESE1986 Volume 34 Issue 7 Pages 2698-2709
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy means of differential scanning calorimetry and polarizing microscopy, the transition paths, temperatures, enthalpies and isopiestic heat capacities were measured for four mesogenic esters, i.e. cholesteryl myristate (ChM), palmitate (ChP), stearate (ChS), and oleate (ChO). By using the above-mentioned thermodynamic quantities, relative chemical potential diagrams were constructed to clarify the thermodynamic phase stability of each ester. The viscosity behavior of each ester was measured at various temperatures under various conditions : continuous heating and cooling as well as isothermal. The effect of thermal history before the isothermal measurements was also examined. On the basis of chemical potential and viscometric diagrams, the phase stability of each ester with or without the influence of shear in the viscometer is discussed. Each ester in cholesteric phase was estimated to behave as a "continuum" without shear, but as a "swarm" under shear. The nature of the peak or hump in the transtion region between isotropic and cholesteric phases is also discussed.View full abstractDownload PDF (1122K) -
YOSHIHIRO NITTA, YASUSHI ARAKAWA, NAOTO UEYAMA1986 Volume 34 Issue 7 Pages 2710-2718
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of primary alkyl esters of phosphorus oxyacids with p-toluenesulfonic acid (TsOH) in refluxing solvents gave the correspondinf p-toluenesulfonates (TsOR). We found that the secondary alkyl esters reacted with TsOH at lower temperature (r.t.-40°C) to afford TsORs in good yields. It is suggested that sulfonic acids may be useful for the selective dealkylation of mixed esters.View full abstractDownload PDF (908K) -
TAKAO SAKAMOTO, YOSHINORI KONDO, RYO WATANABE, HIROSHI YAMANAKA1986 Volume 34 Issue 7 Pages 2719-2724
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSthe cross-coupling reaction of 2-chloro-3-iodo- and 4-chloro-3-iodopyridines with phenylacetylene in the presence of dichlorobis(triphenylphosphine)palladium occurred at the 3-position. The 3-ethynylpyridines containing an adjacent chloro group were convertible to thienopyridines by traatment with sodium hydrosulfide. Similarly, various thieno[2, 3-d]pyrimidines were synthesized from 4-chloro-5-iodopuyrimidines. One-step synthesis of furopyridines by the palladium-catalyzed reaction of iodohydroxypyridines with terminal acetylenes is also described.View full abstractDownload PDF (629K) -
KIMIO FURUHATA, KATSUKO ANAZAWA, MASAYOSHI ITOH, YOSHIYASU SHITORI, HA ...1986 Volume 34 Issue 7 Pages 2725-2731
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of methyl 5-acetamide-4, 7, 8, 9-tetra-O-acetyl-2-chloro-2, 3, 5-trideoxy-D-glycero-β-D-galacto-2-nonulopyranosonate with 1, 6-anhydro-2, 2', 3, 3', 4', -penta-O-benzyl-β-D-lactose in the presence of mercury cyanide and mercury bromide gave a 1 : 1 mixture of the two anomers of the (2→6) linked trisaccharide. O-(Methyl (5-acetamide-4, 7, 8, 9-tetra-O-acetyl-3, 5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate)-(2→6)-O-(2, 3, 4-tri-O-benzyl-β-D-galactopyranosyl)-(1→4)-1, 6-anhydro-2, 3-di-O-benzyl-β-D-glucopyranose and the corresponding β-(2→6) linked isomer could be isolated by chromatography. A deprotection sequence, acetolysis, hydrogenolysis, deacetylation and saponificaiton led to O-(5-acetamide-3, 5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-O-β-D-galactopyranosyl-(1→4)-D-glucopyranose and to the corresponding β-(2→6)linked compound.View full abstractDownload PDF (689K) -
YOSHIO TAKAHASHI, HARUO YAMASHITA, SUSUMU KOBAYASHI, MASAJI OHNO1986 Volume 34 Issue 7 Pages 2732-2742
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stereoselective synthesis of cis-3-amino-4-(1-hydroxyalkyl)azetidin-2-ones from L-aspartic acid is described. The thermodynamically less stable isomers with 3, 4-cis stereochemistry, key intermediates for the synthesis of various substitutes monobactams, were obtained by hydrogenation of the 3-oxyimino-azetidin-2-ones prepared from azetidin-2-ones and isoamyl nitrite. Furthermore, some simple analogues of monobactams were synthesized.View full abstractDownload PDF (1234K) -
CHEN ZHENGXIONG, HUANG HUIZHU, WANG CHENGRUI, LI YUHUI, DING JIANMI, U ...1986 Volume 34 Issue 7 Pages 2743-2746
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new naphthalene derivative, hongconin, was isolated from the rhizome of Eleutherine americana MERR. et HEYNE (Iridaceae), together with three known naphthalene derivatives (1-3). The structure of hongconin was elucidated as 4 on the basis of chemical and spectral studies, and X-ray analysis.View full abstractDownload PDF (505K) -
TAKASHI KURIHARA, MASUO MIKI, RYUJI YONEDA, SHINYA HARUSAWA1986 Volume 34 Issue 7 Pages 2747-2753
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBoron trifluoride-catalyzed allylic rearrangement of the cyanophosphates of α, β-unsaturated ketones (1a-d, 7 and 14) was found to give the allylic phosphates (3a-d, 9 and 16), which were successfully converted to β-cyano-α, β-unsaturated ketones (6a-d, 13 and 20) by acid hydrolysis (0.5 N HCl) followed by manganese dioxide oxidation of theresulting allylic alcohols (5a-d, 11, 12 and 17). The stereochemical features of the allylic phosphates (9 and 6) are discussed.View full abstractDownload PDF (773K) -
TAKAO SAKAMOTO, MASAYUKI AN-NAKA, YOSHINORI KONDO, HIROSHI YAMANAKA1986 Volume 34 Issue 7 Pages 2754-2759
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hydration of o-ethynylbenzoic acid derivatives, such as ethyl o-ethynylbenzoate, o-ethynylbenzonitrile, and o-ethynylbenzamide, in sulfuric acid in the presence of marcuric sulfate, afforded 3-substituted isocoumarins. The palladium-catalyzed reaction of o-halobenzoic acid derivatives with terminal acetylenes to obstain the starting materials for the cyclization is also described.View full abstractDownload PDF (581K) -
TAKAO SAKAMOTO, NORIO MIURA, YOSHINORI KONDO, HIROSHI YAMANAKA1986 Volume 34 Issue 7 Pages 2760-2765
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA five-step synthesis of aaptamine, a marine alkaloid containing a benzo[d, e][1, 6]naphthyridine ring, from 6, 7-dimethoxy-8-nitro-1(2H)-isoquinolone was accomplished in satisfactory yield. As a basis for the above synthesis, a facile preparation of 6, 7-dimethozy-1(2H)-isoquinolones from 3, 4-dimethoxybenzaldehydes was developed using the palladium-catalyzed reaction of o-bromobenzaldehyde derivatives with trimethylsilylacetylene as a key reaction.View full abstractDownload PDF (666K) -
YASUO SHIMADA, TENJI KONISHI, SHIU KIYOSAWA, MASATOSHI NISHI, KAZUMOTO ...1986 Volume 34 Issue 7 Pages 2766-2773
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of two compounds, AH1 and AH2, isolated from agalwood "Jinko" were studied. AH1 was obtained as needles having a melting point different from that of agarotetrol (powder) isolated and characterized by Yoshii et al. However, the carbon-13 nuclear magnetic resonance (13C-NMR) data and [α]D values of the two compounds were identical, and AH1 was concluded to have the same structure, including stereochemistry, as agarotetrol. The half-chair conformation of the hexenyl ring moiety assumed by Yoshii et al. was confirmed by detailed analyses of the proton nuclear magnetic resonance (1H-NMR) and 2D-COSY spectra.AH2 was assigned the structure (5S, 6R, 7R, 8S)-2-(2-phenylethyl)-5e', 6e, 7e, 8'e-tetrahydroxy-5, 6, 7, 8-tetrahydrochromone, a stereo-isomer of agarotetrol (7S, 8R), on the basis of the 1H-NMR, X-ray analysis and circular dichroism (CD) spectral data. It was named isoagarotetrol. The hexenyl ring moiety of isoagarotetrol was found to have a half-chair conformation identical to that of agarotetrol in the crystalline state as well as in solution.View full abstractDownload PDF (756K) -
FUMIKO ABE, TATSUO YAMAUCHI, TOSHIHIRO FUJIOKA, KUNIHIDE MIHASHI1986 Volume 34 Issue 7 Pages 2774-2779
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMinor cardenolide glycosides, including 3-O-(4, 6-dideoxy-3-O-methyl-Δ3-D-hexosulosyl)-affinogenin Ld (affinoside O), 3-O-(4, 6-dideoxy-3-O-methyl-D-allosyl)-affinogenin H (affinoside N), and Δ16-affinoside M (affinoside I) were isolated along with the 3, 16-diacetate of 2β, 3β, 14, 16β-tetrahydroxy-11-oxo-5β, 14β-card-20(22)-enolide (affinogenin D-VI), from the leaves of Anodendron affine DRUCE. The conformations of rings A and B in the doubly linked glycosides and free aglycones are discussed.View full abstractDownload PDF (635K) -
MIKIO OHTSUKA, YOSHIHORI FUJIMOTO, NOBUO IKEKAWA1986 Volume 34 Issue 7 Pages 2780-2785
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethyl esters of acetylene carboxylic acids (2 and 3), an α-bromo acid (4), and α, α-difluoro acids (5 and 6) were synthesized as analogues of the C-24 carboxylic acid which is an intermediate in the microbial degradation of sterol side chains, and these compounds were shown to be inhibitors of the degradation reaction.View full abstractDownload PDF (686K) -
TAKUSHI KURIHARA, TATSUYA TERADA, SHIGEYO SATODA, RYUJI YONEDA1986 Volume 34 Issue 7 Pages 2786-2798
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 1, 1-dimethylindene-3-carbonyl chloride (9), prepared from 3, 3-dimethylindanone (5) via a four step sequence, with ethyl 3-(N-tert-butoxycarbonyl-N-methyl)aminopropionate (14)or its 2-methyl derivative (15) in the presence of lithium diisopropylamide (LDA) gave the β-keto esters (16 and 17). De-tert-butoxycarbonylation of 16 followed by treatment with sodium bicarbonate did not give 12, while 17 afforded the cyclized β-keto ester (19) in good yield. Sodium borohydride reduction of 19 followed by treatment with methanesulfonyl chloride gave the mesylate (21), which was reacted with 1, 8-diazabicyclo[5.4.0]-7-undecene (DBU) to give the unsaturated ester (22). By analogous reaction sequences, the diethylamide derivative (2) was synthesized in moderate yield. Reaction of the β-keto ester (16) with diethyl phosphorochloridate in the presence of LDA gave the enolphosphate (30), which was converted to the unsaturated esters (31a and 31b) in good yields. However, dephosphorylation of 31 failed. Sodium borohydride reduction of 16 gave the alcohol (33), which was converted to the diene ester (34) or the mesylate (36). These were successfully converted to the ethyl 1, 2, 3, 9a-tetrahydro-9H-indeno[2, 1-b]pyridine-3-carboxylates (32s and 32b), which were found to exist in an equilibrium mixture, in excellent yields, respectively. The stereochemistry of some of the key intermediates and of the target compounds is discussed.View full abstractDownload PDF (1309K) -
ICHIYA NINOMIYA, CHIYOMI HASHIMOTO, TOSHIKO KIGUCHI, TAKEAKI NAITO1986 Volume 34 Issue 7 Pages 2799-2809
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA general synthetic route was developed to the despyrrole analogues of a group of clavine alkaloids; virtually no previous synthetic work on these compounds has been reported.View full abstractDownload PDF (1066K) -
MITSUAKI WATANABE, SADAYOSHI HISAMATSU, HIROSHI HOTOKEZAKA, SUNAO FURU ...1986 Volume 34 Issue 7 Pages 2810-2820
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of lithated N, N-diethylsenecioamide and N, N-diethy-3-phenlisocrotonamide with methoxy-substituted benzynes, generated in situ from methoxy-substituted halobenzenes, gave regiospecifically various 3-methyl- and 3-phenyl-naphthol derivatives in a one-pot process. Methoxy-substituted 3-methyl-1-naphthols thus obtained were easily converted into various 1, 4-naphthoquinones and 1, 2-naphthoquinones including biologically active natural products such as plumbagin, plumbagin methylether, 5, 6-dimethoxy-2-methyl-1, 4-naphthoquinone, and 8-methoxy-3-mathyl-1, 2-naphthoquinone.View full abstractDownload PDF (954K) -
KAYOKO OKAMOTO, ISUKE IMADA, TETSUJI IMAMOTO1986 Volume 34 Issue 7 Pages 2821-2827
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-(10-Hydroxydecyl)-2, 3-dimethoxy-5-methyl-1, 4-benzoquinone (CV-2619) and related compounds (the corresponding hydroquinone and hydroquinone monosulfate forms) inhibited lipid peroxidation, especially that initiated with ferrous ion in microsomes of rat liver and canine brain. The fact that CV-2619 inhibited the Fe2+ -dependent peroxidation of the membrane lipid in microsomes and linolenic acid indicated that CV-2619 itself possesses antioxidant activity, like its hydroquinone form. However, CV-2619 barely inhibited lipid peroxidation in aged membranes and did not quench hydroxy radicals. It showed some stimulation of peroxide quenching systems, such as horserdish peroxidase and rat liver cytosomal peroxidation-inhibiting protein. These results suggest that CV-2619 mainly inhibits the initial steps of lipid peroxidation.View full abstractDownload PDF (724K) -
KATSUYA AWANO, SEIGO SUZUE, MITSURU SEGAWA1986 Volume 34 Issue 7 Pages 2828-2832
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Nicotinoylpyrazolo[1, 5-a]pyridines were synthesized by the raation of 3-unsubstituted pyrazolo[1, 5-a]pyridines with nicotinoyl chloride hydrochloride. Tetrahydronicotinoyl derivatives were obtained by hydrogenation of the nicotinoyl derivatives. Furthermore, N-substituted derivatives were synthesized by the reaction of the tetrahydronicotinoyl derivatives with alkylating regents or isocyanates. These pyrazolo[1, 5-a]pyridines were tested for inhibitory activity on arachidonic acid induced platelet aggregation in vitro and ex vivo. Some of these compounds showed higher inhibitory activity than aspirin. Among them, 2-methyl-3-(1, 4, 5, 6-tetrahydronicotinoyl)pyrazolo[1, 5-a]pyridine was found to be the most active compound.View full abstractDownload PDF (523K) -
KATSUYA AWANO, SEIGO SUZUE1986 Volume 34 Issue 7 Pages 2833-2839
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure-activity relationship of 3-(p-substituted benzoyl)pyrazolo[1, 5-a]pyridine derivatives as inhibitors of rabbit platelet aggregation in vitro have been examined. The cluster analysis approach to hte selection of substituents on the phenyl ring of 2-isopropyl-3-(p-substituted benzoyl)pyrazolo[1, 5-a]pyridine was used, and the effect of substituents was investigated by quantitative regression analysis. The p-dimethylamino group was found to be the most effective p-substituent on the phenyl ring for antiaggregant activity.View full abstractDownload PDF (560K) -
KANJI MEGURO, HIROYUKI TAWADA, YASUO SUGIYAMA, TAKESHI FUJITA, YUTAKA ...1986 Volume 34 Issue 7 Pages 2840-2851
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of a search for new antidiabetic agents, 4-oxazolealkanoic acid derivatives (III) were synthesized and tested for hypoglycemic activity in mice. 4-Oxazoleacetic acids (IIIb) bearing a styryl or a suitable aliphatic hydrocarbon moiety at the 2-position showed potent activity. The synthesis and structure-activity relationships of these compounds are presented.View full abstractDownload PDF (915K) -
AKIO MIYAKE, KATSUMI ITOH, YOSHIKAZU OKA1986 Volume 34 Issue 7 Pages 2852-2858
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new angiotensin converting enzyme (ACE) inhibitor, N-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-N-(indan-2-yl)glycine (9a), was found as a result of extensive studies on the structural requisites for the C-terminal amino acid moiety in ACE inhibitors. The synthesis and the determination of the absolute configuration of 9a are described.View full abstractDownload PDF (742K) -
HIROYUKI YAMAGUCHI, HIROMICHI MATSUURA, RYOUJI KASAI, KENJI MIZUTANI, ...1986 Volume 34 Issue 7 Pages 2859-2867
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHigh-performance liquid chromatography (HPLC) of borate complexes on a basic ion-exchange column was investigated for the separation of saponins of Ginseng, Sapindus mukurossi and Anemone rivularis, as well as other synthetic glycosides including steviol glycosides. It was found that HPCL in this mode is effective for analysis and preparative separation of a variety of glycosides, especially isomeric glycosides, containing xylopyranosyl, arabinofuranosyl or arabinopyranosyl units.View full abstractDownload PDF (662K) -
NAOMICHI FUKUDA, MICHIKO YONEMITSU, TAKEATSU KIMURA1986 Volume 34 Issue 7 Pages 2868-2872
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new diterpene glucoside, borapetoside B (1), and its aglycone, borapetol B (2), were isolated from the stems of Tinospora tuberculate BEUMEE as the bitter principles, and their structures were elucidated.View full abstractDownload PDF (497K) -
RIKIO IKENISHI, TAKAYASU KITAGAWA, EIZO HIRAI1986 Volume 34 Issue 7 Pages 2873-2879
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA fluorometric method for the determination o 1-(2-o-chlorobenzoyl-4-chlorophenyl)-5-glycylaminomethyl-3-dimethylaminocarbonyl-1H-1, 2, 4-triazole hydrochloride dihydrate (1) was established. This highly sensitive method was applied to the analysis of animal feed spiked with the drug. Compound 1 was easily transformed into the fluorophore 4-amino-7-chloro-5-(o-chlorophenyl)-[1, 2, 4]triazolo[1, 5-a]quinoline-2-carboxylic acid (2) in alkaline solution. After the extraction of 1 from the feed, 1 was converted into 2. The strong fluorescence of 2 allowed the establishment of a method with a quantitation limit of 5 mg/kg.Compound 1 in feed samples spiked at 10-500mg/kg was determined with a coefficient of variation of less than 10%. The concentration of 1, its uniformity in the whole feed and its stability can be evaluated by this method.View full abstractDownload PDF (637K) -
YUTAKA SAITO, YUKIKO OKAZAKI(INDEN), SHOKO YANO(WADA), ATSUKO KANETSUN ...1986 Volume 34 Issue 7 Pages 2880-2884
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn extremetly sensitive spectrofluorimetric method for assay of human serum albumin (HSA) was developed, based on binding of chrome-azurol S(CAS) by HSA. The CAS-HSA complex shows a fluorescence at 616nm, whereas CAS alone exhibits only a weak fluorescence at this wavelength. A nonionic detergent, polyethylene glycol-p-nonylphenyl ether n=10, acts as a stabilizer of the CAS-HSA complex. The calibration curve was linear in the range from 5 to 80 μg of HSA in the final solution. Relative standard deviation was 1.3% (n=10). The method requires less than one-thirtieth of the amount of HSA required by the control bromcresol green method. HSA values in control sera and spinal fluid assayed by the new method were in agreement with those obtained by the control bromcresol green method.View full abstractDownload PDF (529K) -
YUTAKA SAITO, MASAKI MIFUNE, TERUHISA KAWAGUCHI, JUNICHI ODO, YOSHIMAS ...1986 Volume 34 Issue 7 Pages 2885-2889
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn an attempt to develop good artificial mimesis of catalase, the catalase-like catalytic activity of common ion-exchange resins modified with various metalloporphyrins was estimated in terms of their activity to accelerate in the decomposition of hydrogen peroxide. The anion exchange-resin modified with manganese-tetrakis(sulfophenyl)porphine was found to be the best. This resin retained its activity after repeated use (ten times). The presence of manganese or cobalt as a central metal ion was found to be essential for the activity.View full abstractDownload PDF (501K) -
MASAHIKO TOHMA, REIJIRO MAHARA, HIROMI TAKESHITA, TAKAO KUROSAWA, SHIG ...1986 Volume 34 Issue 7 Pages 2890-2899
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1β-Hydoxylated lithocholic (10a), deoxycholic (10b), chenodeoxycholic (10c) and cholic (10d) acids were synthesized from the corresponding bile acid methyl esters (1a-d) as starting materials. The Δ1-unsaturated ketones (6a, e-g) were prepard from the 3-oxo bile acid esters (2a-d) via reductive debromination of their 2, 4-dibromides (3a, e-g) with chromous acetate and dehydrobromination with lithium carbonate-lithium bromide, and oxidized with alkaline hydrogen peroxide to give the 1β-2β-epoxyketones (7a, e-g). Reductive cleavage of the epoxides (7a, e-g) and subsequent reduction with sodium borohydride afforded the 1β, 3α-dihydroxy compounds (9a, e-g), which were hydrolyzed to the 1β-hydroxylated bile acids (10a-d). 1β, 3α, 12α-Trihydroxy-5β-cholan-24-oic acid (10b) was identified in the urine of healthy men and patients with kidney disease by gas chrmatography-mass spectrometric analysis. Novel 1β, 3α, 7α-trihydroxy-(10c) and 1β, 3α, -7α, 12α-tetrahydroxy-5β-cholan-24-oic acids (10d) were detected in human meconium.View full abstractDownload PDF (1055K) -
Jos H. BEIJNEN, OEDS A.G.J. VAN DER HOUWEN, HILDE ROSING, WILLY J.M. U ...1986 Volume 34 Issue 7 Pages 2900-2913
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinetics and mechanisms of the degradation of mitomycin A and mitomycin B in aqueous solution were investigated by means of ultraviolet (UV) spectrophotometry and high-performance liquid chromatography (HPLC). The influences of pH, buffers and temperature on the degradation were quantified. Degradation products were isolated and characterized by mass spectrometry (MS), UV-VIS spectrophotometry, chromatography and circular dirchroism (CD) spetroscopy. The degradation reactions follow (pseudo) first-order kinetics. The collected kinetic data allowed an accurate determination of the pKa value of the aziridine moiety of the mitomycins by using computerized curve-fitting models.View full abstractDownload PDF (1179K) -
HIROSHI HOSODA, NORIHIRO KOBAYASHI, SAKIKO TAMURA, MIZUE MITSUMA, JUN- ...1986 Volume 34 Issue 7 Pages 2914-2918
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe production of a monoclonal antibody to 11-deoxycortisol is described. Spleen cells from BALB/c mice immunized with 4-(2-carboxyethylthio)-11-deoxycortisol linked to bovine serum albumin were fused with P3-NS1/1-Ag4-1 myeloma cells. A hybridoma clone (S.CET.M8.1.1) was established that secreted immunoglobulin G1 (IgG1) with a high affinity for 11-deoxycortisol (Ka=2×1010M-1). The specifictity of the monoclonal antibody (CET-M8) was assessed by crossreaction studies wiht closely related steroids and by measuring the amount of 11-deoxycortisol in human plasma specimens by means of radioimmunoassay, in comparison with that of a conventional polyclonal antiserum. The results showed that the monoclonal antibody is reasonably specific and useful for the determination of plasma 11-deoxycortisol levels in the metyrapone test.Factors influencing the specificity of monoclonal antibodies to steroids are discussed.View full abstractDownload PDF (601K) -
SHUICHI MIYAURA, HIDEO ISONO1986 Volume 34 Issue 7 Pages 2919-2925
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the previous study, carboxymethyl (CM)-cellulose chromatography of a rabbit liver extract gave at least four glutathione S-transferase activity peaks (peaks R1, R2, R3 and R4).Further purification of peaks R2 and R3 by S-hexylglutathione Sepharose 6B and hydroxylapatite chromatography resolved peak R2 into one peak (a homodimer of the Y2Y2 subunits; Y2 Mr 25000), and peak R3 into two peaks, R3a (a heterodimer of the Y1Y3 subunits; Y1 Mr 24500; Y3 Mr 26500) and R3b (a homodimer of the Y3Y3 subunits). In the present study, isoelectric focusing was used to separate the diethylaminoethyl (DEAE)-flow-through fraction into at least eight activity peaks (pIs 10.95-10.77, 10.35, 9.95, 9.40, 8.88, 8.48, 8.36 and 7.66), which were designated as activity peaks I, II, III, IV, V, VI, VII and VIII in decreasing order of isoelectric point. On the other hand, these peaks could be resolved into at least seven activity peaks by conventional CM-cellulose chromatography, the four main activity peaks of which were assigned as peaks R1, R2, R3 and R4 reported previously. As a result of the individual isoelectric focusing of peaks R1-R4, activity peak I having the highest and broadest isoelectric point was identified as peak R4. By sodium dodecyl sulfate (SDS)/polyacrylamide-gel electrophoresis, peaks II, III and VII were identified as the previously characterized R3a, R3b and R2, respectively. The isoelectric focusing of peak R1 gave four activity peaks (pIs 9.72, 8.56, 7.64 and 7.07). The enzyme wiht pI 9.72 was found to be a homodimer of the Y1Y1 subunits and the other three enzymes were all heterodimers of Y2 subunit and a new type of subunit (designated as Y4 : Mr 28000). Among these four peaks, the enzymes with pIs 9.72 and 7.07 could not be observed in the isoelectric focusing pattern of the gross DEAE-flow-through fraction. The enzymes with pIs 8.56 and 7.64 were identified as peaks VI and VIII, respectively, on the basis of SDS/polyacrylamide-gel electrophoresis and their isoelectric points.View full abstractDownload PDF (824K) -
TOSHIKI MATSUURA, KAZUHIRO OWADA, MITSUAKI SANO, SHINICHI SAITO, ISAO ...1986 Volume 34 Issue 7 Pages 2926-2930
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChanges of methylglyoxal (MG) level accompanying the changes of glyoxalase I and II activities were examined in the liver and blood of mice inoculated with L1210 leukemia or Sarcoma 180 intraperitoneally. The amounts of MG in the liver and blood decreased for the first 3-5d after the inoculation of L1210 leukemia or Sarcoma 180 and then increased significantly. Glyoxalase I and II activities, on the other hand, increased for the first 3-5d and then decreased on day 8. The levels of dihydroxyacetone phosphate, glyceraldehyde-3-phosphate and fructose-1, 6-diphosphate decreased gradually during the experimental period of 8d in the liver and blood of mice with Sarcoma 180.The present observations may suggest that the initial proliferation of the tumor cells is accompanied with a decrease of MG and further development of the tumor cells results in an inductive increase of MG level due to the acceleration of sugar catabolism and/or to the decrease of glyoxalase I and II activities.View full abstractDownload PDF (555K) -
MAKOTO NISHIKATA, HIDEYOSHI YOKOSAWA, SHIN-ICHI ISHII1986 Volume 34 Issue 7 Pages 2931-2936
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPeptide aldehydes are potent inhibitors of serine and cysteine proteases. In the present work, N-benzyloxycarbonyl (Z) dipeptides containing prolinal at the carboxyl terminus were syntheized as inhibitors of prolyl endopeptidases. Since no aldehyde proton was detected by proton nuclear magnetic resonance (1H-NMR) spectrometry, a cyclic structure was proposed for these peptides. Compounds with a Z-L-X-L-prolinal structure were strong inhibitors of prolyl endopeptidases from the ascidian, Halocynthia roretzi, and Flavobacterium meningosepticum. The potency was in the order of Z-L-Val-L-prolinal≃Z-L-Ile-L-prolinal>Z-L-Phe-L-prolinal>Z-L-Ala-L-prolinal with IC50 values of 10-8-10-6 M order for both enzymes. Conversion of the aldehyde into an alcohol or an acid moiety resulted in a considerable decrease in the inhibitory activity. The diastereomers of Z-L-Phe-L-prolinal were much less inhibitory. This result is not compatible with the reported stereospecifity of the Flavobacterium enzyme for its substrated [T. Yoshimoto, R. Walter and D. Tsuru, J. Biol. Chem., 255, 4786 (1980)]. This implies that the open species binds preferentially to the enzyme active site.View full abstractDownload PDF (693K) -
TETSURO NAGASAWA, HIKOKICHI OURA, GEN-ICHIRO NONAKA, ITSUO NISHIOKA1986 Volume 34 Issue 7 Pages 2937-2943
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present investigation was undertaken to evaluate the effect of rhatannin (condensed tannin purified form Rhei rhizoma) on transamination from glutamine by measuring the individual amino acids formed from α-keto analogues of amino acids with glutamine or glutamane or glutamate in the supernate of rat liver homogenate. Increased glycine formation was observed 2 to 4h after the intraperitoneal administration of rhatannin (12.5mg/kg body weight). Glutamate (derived from glutamine via glutaminase) may not participate in the rhatannin-induced elevation of glyoxylate amination by glutamine. This effect by rhatannin was completely abolished by cycloheximide treatment 30 min prior to rhatannin treatment, while actinomycin D had no effect. With 20 mM glutamine as the amino-donor, the order of effectiveness of 20 mM keto analogues of amino acids was glyoxylate>pyruvate>hydroxypyruvate>phenylpyruvate>α-ketoisocaproate, and little activity was observed with α-ketoisovalerate. Phenylalanine and leucine production rates were enhanced with either glutamine or glutamate in rhatannin-treated rats.The results of the present investigation suggest that the hepatic glutamine transaminase pathway might be enhanced in rhatannin-treated rats. This enhancement might be associated with a protein synthesis process.View full abstractDownload PDF (699K) -
KEIKO SAKAI, KOHJI UENO, YUNOSUKE OGAWA, HARUMI OKUYAMA1986 Volume 34 Issue 7 Pages 2944-2949
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe fatty acid compositions of plasma phosphatidylcholine, cholesterol ester, triacylglycerol and free fatty acid fractions were determined in young atopic patients and age-matched controls.No difference was observed in the lipid contents or the fatty acid compositions between the atopic patients and controls. When compared with adult controls, plasma lipids from young children had significantly different fatty acid patterns; the proportions of total linoleate (n-6) series fatty acids and the linoleate/arachidonate ratio were not statistically different, but teh proportions of alpha-linolenate (n-3) series fatty acids were much less, particularly in the phosphatidylcholine, triacylglycerol and cholesterol ester fractions, in young children. These results do not provide rationale for the use of gamma-linolenic acid for atopic therapy. The possible usefulness of providing alpha-linolenate series fatty acid supplementation for children is discussed.View full abstractDownload PDF (568K) -
TARO OGISO, YOSHIMASA ITO, MASAHIRO IWAKI, TORU YAMAHATA1986 Volume 34 Issue 7 Pages 2950-2956
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe initial decline in blood concentration of valproic acid (VPA) was followed by a first-order process in rats given the drug intravenously (i.v.)(60mg/kg) or orally (80mg/kg), but later a secondary increase in drug concentration, resulting from enterohepatic circulation of free and conjugated drugs, was observed. In order to describe the blood concentration pattern of VPA with its pronounced secondary peak, a pharmacokinetic model consisting of central, bile and intestinal compartments was applied. Inclusion in the model of n segments (n=4 in the i.v. dose and n=5 in the oral) of gut lumen for drug transfer from the bile compartment to the absorption compartment improved the agreement between observed and predicted plasma VPA levels. Measurements of the extent of biliary excretion and reabsorption of VPA from bile in bile duct-cannulated rats were done to calculate some parameters. The pharmacokinetic model was justified by the good agreement with observed data obtained after i.v. and oral administrations of VPA in rats. This model was considerably superior to a standard two-compartment pharmacokinetic model.View full abstractDownload PDF (659K) -
KUNIO KOBAYASHI, AYUMI IGAKI, MASAKO KIMURA, TAKAFUMI SAKOGUCHI, MITSU ...1986 Volume 34 Issue 7 Pages 2957-2962
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGliclazide, 1-(3-azabicyclo[3.3.0]oct-3-yl)-3-(p-tolylsulfonyl)urea, an oral hypoglycemic drug having the sulfonylurea structure, was completely degraded in a medium containing more than 0.2M chloride or bromide ion at 37°C after 24h. Other sulfonylureas, tolazamide and glycopyramide, were also degraded in the presence of chloride ion, but tolbutamide, acetohexamide, chlorpropamide and glibenclamide were not. Fluoride, carbonate, acetate, sulfate and phosphate ions and both sodium and potassium cations induced slight degradation of gliclazide. Two degradation products were isolated, crystallized, and identified as a hydrazine compound (3-azabicyclo[3.3.0]oct-3-yl-amine monohydrochloride) and p-toluenesulfonamide based on mp, ultraviolet, infrated, proton nuclear magnetic resonance, mass spectra and high performance liquid chromatography data. The anion-induced gliclazide degradation was dose-dependently depressed by human serum albumin or other proteins. It was completely depressed by albumin at over 0.3 mg/ml. Other serum proteins, α, β and γ-globulins, depressed the anion (Cl-)-induced gliclazide degradation similarly to albumin.View full abstractDownload PDF (632K) -
YOSHITAKA YANO, KIYOSHI YAMAOKA, HISASHI TANAKA1986 Volume 34 Issue 7 Pages 2963-2966
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn automated system for in vitro drug dissolution testing was developed around the PC-9801 or PC-8801 series of personal computers. The hardware consists of the standard dissolution vessel, a ultravioled (UV) detector, an intelligent A/D converter and a personal computer which is connected with an XY-plotter. The fluid in the dissolution vessel is recirculated between the vessel and the UV detector by a pump through fine polyethylene tubing. The signals from the A/D converter, which is connected with the UV detector, are taken into the personal computer through the RS-232C interface. A program (Automated Dissolution Measurement Program ADMP) was written in BASIC to control the A/D converter, to store the dissolution data on floppy disk, to plot the time course of dissolution on CRT and XY-plotter, and to calculate the dissolution parameters, such as the 50% dissolution time (t50) and the mean dissolution time (MDT).View full abstractDownload PDF (444K) -
HITOSHI TADA, YOSHINORI SAGAE, TOSHIO SUZUKI, KATSUO UNNO1986 Volume 34 Issue 7 Pages 2967-2972
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe influence of dietary fat intake on the plasma levels and bioavailability of isosorbide dinitrate (ISDN) from two sustained-release formulations was examined in ten healthy volunteers by mean of an open crossover trial. Each subject orally received one mixed granule type product(formulation A) and one diffused-sustained-release type product (formulation B). The plasma level of ISDN rapidly increased to the maximum level within 3-5h after administration of each product in subjects on a fatty diet. The mean enhancements were 84.5% for formulation A and 61.2% for formulation B compared with the levels in subjects on fat-free diet. The area under the curve(AUC0-10) values of the former in subjects fed dietary fat were significantly greater than the preprandial figures, but no significant difference was observed with the latter product.View full abstractDownload PDF (652K) -
MUMIO ISHIBASHI, SUMIE YOSHIOKA, JYUNKO MONMA, YASUO SUZUKI, MITSURU U ...1986 Volume 34 Issue 7 Pages 2973-2978
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe adsorption of potassium ion by synthetic hydrated aluminum silicates (zeolites) was studied to examine the feasibility of application of zeolites as oral adsorbents for the treatment of hyper-kalemia. In vitro and in vivo adsorption studies indicated that one of the zeolites studied(ZPC-10A) had superior physical characteristics as a potassium ion adsorbent, as compared with conventional adsorbents (polystyrene sulfonates). An acute toxicity study also suggested that ZPC-10A is applicable as an oral adsorbent.View full abstractDownload PDF (551K) -
MAKOTO HAGA, FUMIKO KATO, MASAHITO YOSHIDA, FUTABA KOHARA, YURIKO KATO1986 Volume 34 Issue 7 Pages 2979-2988
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of covalent binding of sialoglycopeptide (GP) derived from fetuin to the liposome surface on the clearance of liposomes from the circulation of rats was investigated. Small unilamellar vesicles (SUV) and two types of multilamellar liposomes (MLV, LMLV) were prepared and coupled with GP without changing the size distribution of the liposomes. The leakage of carboxyfluorescein (CF) from these GP-modified liposomes in plasma was measured in vitro. The clearance of intravenously injected GP-modified liposomes was followed by monitoring entrapped CF and incorporatd [3H]cholesteryl oleate ([3H]CHOL) in the liposomes.It was shown that CF release from GP-modified SUV increased slightly with increasing amount of GP-modification. On the other hand, CF was released more rapidly from GP-modified MLV and LMLV. The circulation times of MLV and LMLV were reduced by the surface modification of the liposomes with GP. In contrast, the clearance of SUV was inhibited significantly by incorporation of GP on the surface of the liposomes. The clearance pattern of negatively charged liposomes containing dicetyl phosphate, which had equivalent ζ potential and similar size distribution to GP-modified SUV, suggests that the prolonged circulation time of GP-modified SUV is not attributable to the negative surface charge of liposomes. These results suggest that surface modification of SUV with sialoglycopeptide derived from fetuin may be a useful technique for designing liposomes with a long circulation time.View full abstractDownload PDF (951K) -
KAZUO MARUYAMA, HIDEO NISHIGORI, MOTOHARU IWATSURU1986 Volume 34 Issue 7 Pages 2989-2993
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe location of Site I on the human serum albumin (HSA) molecule was investigated.Naphthol yellow- S (NY-S) was used as a representative ligand for Site I, since the bilirubin-displacing effect of NY-S was similar to that of Site I drugs such as warfarin and phenylbutazone.NY-S was bound to HSA with at least three classes of binding sites. The binding parameters of the primary class were one binding site (n1=1) and a binding constant (K1) of >107M-1, and the complex at equimolar ratio of dye to albumin exhibited metachromasy. The intrinsic fluorescence intensity, attributed to the single tryptophan residue (position 214), decreased significantly in this complex. Fragments A and C (residues 299-585 and 124-298, respectively, in the amino acid sequence of HSA) obtained by cyanogen bromide cleavage of HSA showed NY-S-binding ability.The binding of NY-S to fragment A or C aused the same metachromasy as seen with NY-S-HSA complex. Fragment C is markedly hydrophobic and contains the single tryptophan residue. The binding of NY-S to HSA was diminished by the chemical modification of lysine residues with pyridoxal 5'-phosphate (PLP). Further, lysine residues modified by PLP existed in fragment C.These results suggest that the primary binding site of NY-S, which corresponds to Site I, is located in the fragment C region of the HSA molecule.View full abstractDownload PDF (516K) -
TOMONARI KUWAYAMA, TAMOTSU YASHIRO, YUKIHISA KURONO, KEN IKEDA1986 Volume 34 Issue 7 Pages 2994-2998
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEstazolam deuterated in the triazole ring was isolated and its carbon-13 nuclear magnetic resonance signals were assigned in relation to those of estazolam. The coupling constant ratio, [numerical formula], for the triazole C-1 atom was 6.66. Rates of hydrogen exchange of estazolam with deuterium were measured at 23°C in acidic aqueous solution (0.5 N DCl) and in methanol-d4 contaning trifluoroacetic acid-d and triethylamine. The exchange reaction was accelerated in the presence of acid or base, indicating that the exchange occurs in a base-catalyzed reaction and that the triazole C-1 atom of estazolam behaves as an acid.View full abstractDownload PDF (530K) -
NORIAKI OHNISHI, TERUYOSHI YOKOYAMA, TSUNEO UMEDA, YOSHIFUMI KIYOHARA, ...1986 Volume 34 Issue 7 Pages 2999-3004
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSustained-release suppositories of indomethacin (IM) were prepared by the use of a solid dispersion system. As the suppository base, we used a solid matrix of polyethylene glycol 2000(PEG) as a water-soluble carrier and hydroxypropylmethylcellulose phthalate (HP55) as a poorly water-soluble carrier. It was observed by X-ray diffractometry that IM was uniformly dispersed in amorphous state in the matrix suppositories. The rectal administration of 20% HP55 matrix suppositories (M-20-5) in rabbits resulted in both fast-release and sustained-release characteristics as well as good bioavailability. The sustained release of IM from the matrix suppositories was attributed to the formation of a network structure of HP55 which dissolved more slowly than PEG.View full abstractDownload PDF (763K) -
MASANORI OKAMOTO, KEIZO YOSHIDA, MOTOAKI NISHIKAWA, KEN-ICHI HAYASHI, ...1986 Volume 34 Issue 7 Pages 3005-3010
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-Methyl-3-[1-[5-methylthiomethyl-6-oxo-3-(2-oxo-3-cyclopenten-1-ylidene)-2-piperazinyl]-ethyl]-2-indolinone (FR-900452), isolated from the fermentation broth of Streptomyces phaeofaciens No. 7739, is a specific inhibitor of rabbit platelet aggregation induced by platelet activating factor (PAF) in vitro. In order to ascertain the PAF antagonistic activity of FR-900452 in vivo, the effects of this compound on PAF-induced bronchoconstriction in guinea-pigs, hypotension in rats and vascular permeability increase in mice were examined. The compound significantly inhibited the bronchoconstriction, the hypotension and the vascular permeability increase at a dosage of less than 10mg/kg, i.v., and the hypotensive actions induced by i.v. administration of histamine (His, 100μg/kg), acetylcholine (Ach, 1μg/kg), bradykinin (Bk, 10μg/kg) and isoproterenol (Isp, 1μg/kg) were not altered by FR-900452 (10mg/kg, i.v.). Therefore, to determine whether endogenous PAF contributes to the pathogenesis of immunoglobulin E (IgE)-mediated anaphylaxis, the effect of FR-900452 on the hypotension induced by IgE-mediated anaphylaxis in rats was tested. The compound significantly prevented the hypotension at a dose of 10mg/kg, i.v. The results suggest that PAF may play a role in the pathogenesis of the IgE-mediated hypotension in rats.View full abstractDownload PDF (611K) -
TAKASHI HIROTA, KEIKO KAWANISHI, KENJI SAKAKI, TETSUTO NAMBA1986 Volume 34 Issue 7 Pages 3011-3014
Published: July 25, 1986
Released on J-STAGE: March 03, 2018
JOURNAL FREE ACCESS4-Alkylamino-5, 6-dihydrobenzo[h]quinazolines (IIIa-k) were synthesized by the reaction of 4-chloro-5, 6-dihydrobenzo[h]quinazoline (IIc) with primary alkylamines. Screening of 4-amino-(IIa), 4-hydroxy-(IIb), and 4-(2-hydroxyethylamino)-5, 6-dihydrobenzo[h]quinazoline (IId), as well as IIc and IIIa-k, for antireserpine action indicated that IId, IIIa, and IIIh exhibited effective antidepressant activity.View full abstractDownload PDF (384K) -
KIMIO HIGASHIYAMA, MIYOKO TOYAMA, HIROTAKA OTOMASU1986 Volume 34 Issue 7 Pages 3015-3019
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVilsmeier-Haack reactions of 1, 3(2H, 4H)-isoquinolinediones (1a, b) with dimethylformamide and POCl3 afforded 4-hydroxymethylene-1, 3(2H, 4H)-isoquinolinediones (2a, b) in good yields.Similar reactions of 1a, b using formanilides instead of N, N-dimethylformamide gave the 4-anilinomethylene compounds (3a, b). Chlorinations of 2a, b with POCl3 in CHCl3 or tetrahydro-furan gave the 4-chloromethylene compounds 4a, b. Treatment of 2a with POCl3 in the absence of solvent afforded 4a and 1, 3-dichloro-4-(dichloromethyl)isoquinoline (5). Compound 2b reacted with various amines including ketone reagents to form the corresponding 4-aminomethylene compounds 7a-e, and 7a-e as well as 3a, b could also be prepared from the reactions of 4b with appropriate amines. Catalytic hydrogenation of 2b resulted in the formation of 2, 4-dimethyl-1, 3(2H, 4H)-isoquinolinedione (8) and 2, 2', 4, 4'-tetramethyl[4, 4'-biisoquinoline]-1, 1', 3, 3'(2H, 2'H-4H, 4'H)-tetrone (9).View full abstractDownload PDF (501K) -
YOSHIO TAKAHASHI, SHIGERU HASEGAWA, TOSHIO IZAWA, SUSUMU KOBAYASHI, MA ...1986 Volume 34 Issue 7 Pages 3020-3024
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(3S)-3-Benzyloxycarbonylamino-γ-butyrolactone was prepared by the regioselective reduction of L-aspartic acid. Alkylation and aldol condensation of the γ-butyrolactone afforded the trans isomer selectively. The resulting 2, 3-trans γ-butyrolactone was hydrolyzed and then cyclized to give the 3, 4-cis β-lactam. By taking advantage of this strategy, key intermediates of epi-PS-5 and carpetimycins were synthesized.View full abstractDownload PDF (621K) -
AIKO MORIGIWA, KATSUAKI KITABATAKE, YOSHINORI FUJIMOTO, NOBUO IKEKAWA1986 Volume 34 Issue 7 Pages 3025-3028
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 70% MeOH extract of Ganoderma lucidum had an inhibitory effect on angiotensin converting enzyme activity, and from this extract, five new triterpenes, named ganoderal A, ganoderols A and B, and ganoderic acids K and S, were isolated. Their structures were determined on the basis of spectral evidence.View full abstractDownload PDF (483K) -
KIMIAKI ISOBE, KUNIHIKO MOHRI, HIROMICHI SANO, JUN-ICHI TAGA, YOSHISUK ...1986 Volume 34 Issue 7 Pages 3029-3032
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemoselective reduction of the ester group in keto-esters was studied. Treatment of potassium (or lithium) enolate anions of β-keto-esters with aluminum hydride reduced the ester group chemoselectively to give β-keto-alcohols in moderate yield. Similar reactions of γ-and δ-keto-esters were not chemoselective, yielding a mixture of the diol and the keto-alcohol.View full abstractDownload PDF (425K) -
YASUO SHIMADA, TENJI KONISHI, SHIU KIYOSAWA1986 Volume 34 Issue 7 Pages 3033-3037
Published: July 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new kinds of phenylethyl chromone derivatives, named AH1A, AH2a and AH2b, were isolated from the crude AH1 (agarotetrol) and AH2 (isoagarotetrol) fractions of agalwood (Jinko)from Kalimantan. AH<1A> separated from the crude AH1 fraction through the process of acetylation was characterized as 2-[2-(4-methoxyphenyl)ethyl]-5α, 6β, 7β, 8α-tetraacetoxy-5, 6, 7, 8-tetrahydro-chromone, and AH2a and AH<2b>, from crude AH2 fraction, were established to be 2[2-(4-methoxyphenyl)ethyl]- and 2-[2-(2-hydroxyphenyl)ethyl]-5α, 6β, 7α, 8β-tetrahydroxy-5, 6, 7, 8-tetrahydrochromone, respectively.View full abstractDownload PDF (467K)