All issues
Volume 31, Issue 8
Displaying 1-50 of 67 articles from this issue
-
TOSHIHIKO OZAWA, AKIRA HANAKI1983 Volume 31 Issue 8 Pages 2535-2539
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of superoxide ion, O2-, with physiologically important quinones were investigated in acetonitrile by electron spin resonance (ESR) spectroscopy. Superoxide ion could reduce quinones such as p-benzoquinone, duroquinone, vitamin E quinone, 1, 4-naphthoquinone and vitamin K3 to yield the corresponding semiquinone radicals. The fact that vitamin E quinone, an irreversible metabolite of vitamin E, was reduced by O2- to the semiquinone radical suggests that, like vitamin E, vitamin E quinone may also scavenge O2- and protect living cells from the effects of O2- in a hydrophobic environment. Further, in view of the apparent reversiblity of the reaction of O2- with vitamin K3, it is unlikely that the in vivo toxicity of vitamin K3 is solely due to O2- production, as has been suggested.View full abstractDownload PDF (455K) -
NOBUYA KATAGIRI, SHUGO ATSUUMI, TETSUZO KATO1983 Volume 31 Issue 8 Pages 2540-2551
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of imidazo[1, 5-a]pyrimidines from 2-substituted pyrimidin-4(3H)-ones is described. 2-[(Acylamino)methyl]-6-methylpyrimidin-4-(3H)-ones, prepared by the reaction of β-aminocrotonamide with N-acylated amino acid esters, were treated with POCl3 to give 2- and 4-chloroimidazo[1, 5-a]pyrimidines, which reacted with various nucleophiles to afford 2- and 4-substituted imidazo[1, 5-a]pyrimidines.View full abstractDownload PDF (753K) -
TAKESHI KATO, YUSHIN NAKAMURA, YUTAKA MORITA1983 Volume 31 Issue 8 Pages 2552-2563
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotodimerizations of N-alkyl-2-pyridones (1a-e), N-ω-carboxyalkyl-2-pyridones (1f-h), and N-2'-carboxyethyl-4-alkyl-2-pyridones (1i and 1j) in micellar and reversed micellar systems gave the following results ; 1) in the reactions of 1a-e, the cis/trans ratios of dimers increased with decreasing concentration of the probes, with the octyl compound (1d) showing the highest selectivity ; 2) in the case of 1f-h, the ratios increased up to 1.0 with decreasing alkyl chain length ; 3) below 7.2 mM concentration, 1i gave exclusively the cis dimer, while only the trans dimer was formed when the reaction was carried out in water. The results indicate that the regio-control of the reactions was a result of the alignment effect of micelles on the substrate, and moreover, in both micellar systems, not only the distribution of amphiphilic probes between micellar and bulk (water or cyclohexane) phases but also the orientation and incorporation site of the pyridone moiety play important roles in the regioselectively for the cis dimer.View full abstractDownload PDF (955K) -
NOBUTAKA KAWAI, TAKAYUKI SHIOIRI1983 Volume 31 Issue 8 Pages 2564-2573
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPropiophenone (11) was conveniently converted to its enamines 12a-c using boron trifluoride etherate as a catalyst. Reaction of diphenyl phosphorazidate (DPPA) with the enamines 12a-c efficiently afforded the N-phosphorylated amidines 14a-c by the 1, 3-dipolar cycloaddition of DPPA to the enamine double bond, followed by the evolution of nitrogen from the intermediate triazoline 13, and 1, 2-migration of the phenyl group. 1, 3-Dipolar dlimination products 15a-c were also formed, though in very low yields. Some chemical properties of the N-phosphorylated amidine 14a, as well as the 1, 3-dipolar character of DPPA, were investigated. By the same reaction sequences (enamine formation followed by the 1, 3-dipolar cycloaddition of DPPA), some alkyl phenyl ketones 29a-c were conveniently converted to the N-phosphorylated amidines 31a, 31b, and 27 via the enamines 30a-c. However, in the case of acetophenone and its derivatives 33a-c, these reaction sequences proceeded sluggishly. Alkaline hydrolysis of the N-phosphorylated amidines 14a, 31a, 31b, and 27 with potassium hydroxide afforded 2-phenylalkanoic acids 25 and 32a-c, respectively, in excellent yields. The overall three-step process of successive treatment of alkyl phenyl ketones (alkyl〓methyl) with pyrrolidine, DPPA, and potassium hydroxide may provide a new general method for the efficient conversion of alkyl aryl ketones to 2-arylalkanoic acids.View full abstractDownload PDF (975K) -
SACHIKO KONDO, MATAO MATSUI, YASUO WATANABE1983 Volume 31 Issue 8 Pages 2574-2577
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new hasubanan ester-ketal alkaloid, named stephabenine, was isolated from the fresh fruits of Stephania japnica MIERS (Menispermaceae). Alkaline hydrolysis of the new base gave benzoic acid and a basic component, whose proton nuclear magnetic resonance spectrum was identical with that of authentic N, O-dimethylstephine.View full abstractDownload PDF (520K) -
TETSUJI KAMETANI, ATSUSHI NAKAYAMA, HIROO MATSUMOTO, TOSHIO HONDA1983 Volume 31 Issue 8 Pages 2578-2582
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA 6-phthalimidolcarbapenem derivative was synthesized by intramolecular Wittig cyclization.View full abstractDownload PDF (615K) -
TOZO FUJII, KOICHIRO YAMADA, SHINZABURO MINAMI, SHIGEYUKI YOSHIFUJI, M ...1983 Volume 31 Issue 8 Pages 2583-2592
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe first total synthesis of alangicine (3), an Alangium lamarckii alkaloid, has been achieved in the form of a racemic modification by means of an initial alkaline hydrolysis of the (±)-tricyclic ester 6 and succeeding steps proceeding through the intermediates (±)-7, (±)-10, and (±)-9. A parallel synthetic route starting with the (-)-tricyclic ester 6, derived from (+)-cincholoipon ethyl ester (8), produced the chiral target molecule (+)-3 with alangicine unequivocally established the structure and absolute stereochemistry of this alkaloid. The 13C nuclear magnetic resonance spectra of (±)-alangicine (3) and the ipecac and Alangium alkaloid psychotrine (18) confirmed their endocyclic double bond structures in the dihydroisoquinoline moiety. Catalytic reductions of 11, (±)-12, and 15 using hydrogen and Pd-C were investigated, and the results have shown that hydrogenolysis of the benzyloxy group proceeds much faster than saturation of the endocyclic C=N bond.View full abstractDownload PDF (1007K) -
MAKOTO NISHIZAWA, TAKASHI YAMAGISHI, GENICHIRO NONAKA, ITSUO NISHIOKA, ...1983 Volume 31 Issue 8 Pages 2593-2600
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTogether with 1, 2, 3, 6-tetra- and 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucoses, homologous series of hexa- and heptagalloylglucoses have been isolated from the tannin fraction of the root of Paeonia lactiflora PALL var. trichocarpa BUNGE. (Paeoniaceae). Their structures were determined by hydrolytic studies and by comparison of the 13C-nuclear magnetic resonance (13C-NMR) spectra with that of pentagalloylglucose. Octa-deca-galloylglucoses were partially purified and their structures characterized mainly by using 13C-NMR spectroscopy. The isolation and structural studies of these galloylglucoses have shown gallotannins in Paeoniae Radix to have a 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose core with depside galloyl groups predominantly at the C-3 and C-6 positions in the glucose residue. Normal-phase high performance liquid chromatographic analysis showed that the gallotannins are composed of tetra-undeca-galloylglucoses having an average molecular weight of 1286, corresponding to 7.3 galloyl groups per glucose molecule. The effects of hexa-deca-galloylglucoses isolated in this study on the urea-nitrogen (BUN) concentration in rat serum were examined, and all these compounds were shown to have remarkable BUN-decreasing activities.View full abstractDownload PDF (728K) -
JUNKO KOYAMA, TERUYO SUGITA, YUKIO SUZUTA, HIROSHI IRIE1983 Volume 31 Issue 8 Pages 2601-2606
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermolysis of cycloalkanone oxime O-allyl ethers in air gave the corresponding cycloal-kenopyridines, providing a new method for the synthesis of cycloalkenopyridine derivatives.View full abstractDownload PDF (573K) -
YASUHIRO TORISAWA, MASAKATSU SHIBASAKI, SHIRO IKEGAMI1983 Volume 31 Issue 8 Pages 2607-2615
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA facile 1, 5-migration of tert-butyldimethylsilyl and tert-butyldiphenylsilyl groups in the Witting reaction and under other basic conditions was observed during synthetic studies on prostaglandins. A new method for the cleavage of these two silyl protecting groups to the parent alcohol was developed by the combined use of potassium superoxide and crown ether in dimethyl sulfoxide. Utilizing these new reactivities, an efficient synthesis of 11-epi-PGF2α from the well known Corey lactone was successfully achieved.View full abstractDownload PDF (951K) -
YOSHIRO KOBAYASHI, TSUTOMU MORIKAWA, TAKEO TAGUCHI1983 Volume 31 Issue 8 Pages 2616-2622
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree types of ring-opening reactions of gem-difluorocyclopropyl carbinols are described ; 1) reaction with hydrobromic acid, 2) reaction with acetic acid in the presence of p-toluenesulfonic acid, and 3) rearrangement through a mesylate. Ring-opening reactions of 1a, d, e having an electron-donating substituent at C3 were found to give β, β-difluorohomoallyl derivatives derived from C1-C3 bond scission. On the other hand, reactions of 1b, c having hydrogen atoms or a methyl group at C3 were not selective or afforded α, α-difluorohomoallyl derivatives (C1-C2 bond scission) preferentially.View full abstractDownload PDF (785K) -
MASANORI SAKAMOTO, YASUNOBU AKIYAMA, NOBUKO FURUMI, KEITARO ISHII, YOS ...1983 Volume 31 Issue 8 Pages 2623-2631
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of various aldimines 4a-f with 4-nitrobenzoyl cyanide (2b) gave the Reissert-type compounds 5a-f. However, reaction of N-(1-phenylpropylidene)benzylamine (7a) with 2b gave 1-benzyl-4-hydroxy-5-imino-3-methyl-4-(4-nitrophenyl)-2-phenyl-4, 5-dihydropyrrole (8a). Similar reactions of 7b, 7c, and 12 with 2b gave the pyrrole derivatives 8b, 11, and 13, respectively. Next, the reaction of N-cyclohexylidenecyclohexylamine (14) with benzoyl cyanide (2a) was reexamined. The structure of the adduct 16 was different from that of the Reissert-type compound 15 described by Dornow and Lupfert.View full abstractDownload PDF (734K) -
SHOJI TAKEMURA, YOSHIKO AZUMA, CHIYUKI SHOGAKI, YASUYOSHI MIKI, HIKARU ...1983 Volume 31 Issue 8 Pages 2632-2638
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA synthetic route to 2-O-(diphenylacetyl)salicylic acid derivatives was developed and the effects of the products on the heat-denaturation of albumin and on heat-induced erythrocytolysis were examined (in vitro anti-inflammation test). Trichloroethyl salicylate was acylated with diphenylacetic acid and its derivatives in the presence of methanesulfonyl chloride and pyridine, and the products were deprotected with zinc-acetic acid to give 2-O-(diphenylacetyl)salicylic acid derivatives. Their biological effects resembled those of ibuprofen.View full abstractDownload PDF (682K) -
ISAO KITAGAWA, SHINJI TSUJII, FUMIKO NISHIKAWA, HIROTAKA SHIBUYA1983 Volume 31 Issue 8 Pages 2639-2651
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid treatment of 1-O-acetyl-10-hydroxygeraniol (5a), 1-O-methyl-10-hydroxygeraniol (5b), 1-O-acetyl-10-hydroxynerol (6a), and 1-O-methyl-10-hydroxynerol (6b) was investigated under various conditions. It was found that treatment of 5a and 6a with HCOOH gave menth-1-ene-8, 9-diol (7), while treatment of 5a, 5b, 6a, or 6b with BF3-etherate in CH2Cl2 furnished two menthofuran-type compounds (9, 10) and two bicyclo[3.2.1]oct-2-ene derivatives (17, 24). Both 9 and 10 were successfully converted to menthofuran (16) and 17 was converted to a bicyclo[3.2.1]octenone derivative (23) which was a key intermediate for a synthesis of juvabione (27).View full abstractDownload PDF (1316K) -
JEAN-CHARLES LANCELOT, JEAN-MARIE GAZENGEL, MAX ROBBA1983 Volume 31 Issue 8 Pages 2652-2661
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of 6, 7-dihydro-5H-pyrimidino[5, 4-c]carbazoles (3) was achieved by cyclisation of 1, 2, 3, 4-tetrahydrocarbazol-4-ones with triformamidomethane. The oxydation with potassium permanganate of 6, 7-dihydro-5H-pyrimidino[5, 4-c]carbazoles gave the 7H-pyrimidino[5, 4-c]carbazoles (4). The reactions of the pyrimidinocarbazoles (4a) and (4e) with lithium organic compounds afforded 4-substituted derivatives (6). The structure of the derivatives was determined by 1H-NMR and Overhauser effect.View full abstractDownload PDF (1007K) -
MITSUAKI WATANABE, HISAKO MAENOSONO, SUNAO FURUKAWA1983 Volume 31 Issue 8 Pages 2662-2668
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRegiospecific and effcient synthesis of anthracyclinones have been achieved by using a directed metalation strategy. The phthalides 5a and 5b were prepared by the condensation of metalated N, N-diethylbenzamide derivatives (1') with dihydronaphthalene carbaldehydes (2a and 2b) or by the reaction of metalated dihydronaphthalene (4') with a phthalaldehydic amide derivative (3). The phthalide (5) was then reduced to the acid (14), which was readily cyclized with trifluoroacetic anhydride to the tetracyclic quinone (6). The tetracyclic quinone (6) was converted into the trione (7), a key intermediate for the synthesis of daunomycinone, by epoxidation and subsequent rearrangement using p-toluenesulfonic acid.View full abstractDownload PDF (760K) -
TAKUO CHIBA, MINORU OKADA, TETSUZO KATO1983 Volume 31 Issue 8 Pages 2669-2676
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Methylenehexahydrocyclobuta[c]quinoline 2 obtained from cyclobuta[c]quinolinespiro-oxetanone 1 was isomerized to 2-methyltetrahydrocyclobuta[c]quinoline 5 by treatment with sodium ethoxide in dry toluene. The reaction of compound 5 with olefins, such as methyl acrylate, acrylonitrile, N-phenylmaleimide, and methyl methacrylate under reflux in dry xylene gave [4+2] cycloadducts, hexahydrophenanthridine derivatives 6-9. Ethoxycarbonylmethyl-cyclobuta[c]quinolines 4 generated by ethanolysis of 1 were treated with thionyl chloride in pyridine to give dehydrated products, (E)-2-(ethoxycarbonylmethylene)cyclobuta[c]quino-line (E)-13 and its isomer (Z)-13. Compounds (E)-13 and (Z)-13 isomerized to the same product, 2-(ethoxycarbonylmethyl)cyclobuta[c]quinoline 14 in the presence of sodium ethoxide in dry benzene at room temperature. Similarly, compound 14 reacted with olefins to give hexahydrophenanthridine derivatives 15-18 via a 2-oxoquinoline-3, 4-diquinomethane intermediate.View full abstractDownload PDF (722K) -
MASASHI TOMODA, KAZUYO SHIMADA, NORIKO SHIMIZU1983 Volume 31 Issue 8 Pages 2677-2684
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA representative mucilage, named Althaea-mucilage R, was isolated from the roots of Althaea rosea CAVAILLES (hollyhock). The final preparation was homogeneous as determined by ultracentrifugal analysis, cellulose acetate and glass-fiber electrophoresis, and gel chromatography. Its water solution gave an intrinsic viscosity value of 33.4. It was composed of partially acetylated acidic polysaccharide and protein in a ratio of approximately 10.3 : 1.0, and its molecular weight was estimated to be 41700. The polysaccharide moiety was composed of D-galactose, D-glucose, L-rhamnose, D-galacturonic acid, and D-glucuronic acid in the molar ratio of 2 : 1 : 6 : 4 : 6. Reduction of carboxyl groups followed by methylation analysis, and partial acid hydrolysis studies made it possible to deduce the structural features of the polysaccharide moiety in the mucilage (Chart 4).View full abstractDownload PDF (868K) -
MIYOJI HANAOKA, KAZUYOSHI NAGAMI, MITSURU INOUE, SHINGO YASUDA1983 Volume 31 Issue 8 Pages 2685-2690
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHeating of tetrahydroberberine (1) in ethyl chloroformate preferentially afforded the C8-N bond cleavage (4) with small amounts of the C6-N and C14-N bond cleavage products (5 and 6, respectively). The urethane (4) was effectively converted to (±)-canadaline (2), a secoberbine alkaloid, and a retroprotoberberine (3).View full abstractDownload PDF (730K) -
YASUMITSU TAMURA, AKIMORI WADA, MANABU SASHO, YASUYUKI KITA1983 Volume 31 Issue 8 Pages 2691-2697
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermal treatment of homophthalic anhydrides (1 and 2) with various dienophiles (3-12) caused cycloaddition with spontaneous extrusion of carbon dioxide to give the corresponding linearly condensed peri-hydroxy aromatic compounds (13-23) in considerable yields. A possible mechanism for these reactions is proposed.View full abstractDownload PDF (736K) -
FUMIO SAKAMOTO, SHOJI IKEDA, GORO TSUKAMOTO1983 Volume 31 Issue 8 Pages 2698-2707
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to investigate a new type of promoiety for ampicillin prodrugs, acyloxyallyl esters were prepared and their oral absorbabilities, stabilities and hydrolyzabilities to parent ampicillin were studied. As starting materials for (3-phthalidylidene)ethyl esters, ethylidenephthalide and its derivatives were regiospecifically prepared by a new method using the Wittig reaction. (3-Phthalidylidene)ethyl esters (14a-c) given orally were well absorbed, but (thiophthalidylidene)ethyl ester (14d) and (isocoumarin-4-yl)methyl ester (14e) were poorly absorbed.View full abstractDownload PDF (886K) -
TADATAKA NORO, TOSHIO MIYASE, MASANORI KUROYANAGI, AKIRA UENO, SEIGO F ...1983 Volume 31 Issue 8 Pages 2708-2711
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMonoamine oxidase (MAO) inhibitor contained in the rhizomes of Kaempferia galanga L. (Zingiberaceae) was isolated and identified as ethyl p-methoxy-trans-cinnamate (I). The type of inhibition with respect to benzylamine by I was competitive.View full abstractDownload PDF (452K) -
MITSUGI KOZAWA, MASAYO FUKUMOTO, YOUKO MATSUYAMA, KIMIYE BABA1983 Volume 31 Issue 8 Pages 2712-2717
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Chinese crude drug "Quiang Huo" (Umbelliferae) afforded three new coumarins, notopterol (7), notoptol (8) and anhydronotoptol (9) together with isoimperatorin (1), bergapten (2), bergaptol (3), nodakenin (4), osthenol (5), demethylfuropinnarin (6), p-hydroxyphenethyl anisate (10), phenethyl ferulate (11) and farcarindiol (12). The structures of 7-9 were established as dl-5[(2E)-5-hydroxy-3, 7-dimethyl-2, 6-octadienyloxy]psoralen, 5-[(2E, 5E)-7-hydroxy-3, 7-dimethyl-2, 5-octadienyloxy]psoralen and 5-[(2E, 5E)-3, 7-dimethyl-2, 5, 7-octatrienyloxy]psoralen, respectively.View full abstractDownload PDF (734K) -
ATSUSHI TAKADA, HARUO NEGISHI, TAKEO UEDA1983 Volume 31 Issue 8 Pages 2718-2723
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo colored substances produced in the thalleioquine reaction using 6-methoxyquinoxaline as a model compound were isolated. The red substance was determined to be an 8, 8'-biquinolinyl derivative (6a), and the blue substance was found to be a super-stable radical compound.View full abstractDownload PDF (644K) -
HIDETOSHI ARAKAWA, MASAKO MAEDA, AKIO TSUJI, HIROSHI NARUSE, EMIKO SUZ ...1983 Volume 31 Issue 8 Pages 2724-2731
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn enzyme immunoassay of 17α-hydroxyprogesterone (17-OHP) in dried blood spotted onto filter paper has been developed. 17-OHP was conjugated to horseradish peroxidase by the mixed anhydride method. Separation of free and bound 17-OHP-peroxidase conjugate was done by the use of insolubilized antibody, prepared by coating polyacetal beads with purified immunoglobulin G (IgG) of goat anti-rabbit IgG serum. The enzyme activity was measured by the fluorophoto-metric method using 3-(p-hydroxyphenyl)propionic acid and H2O2 as substrates. The sensitivity of the present method was 1.0 pg/tube for 17-OHP. The intra-and interassay coefficients of variation were 5.4-7.0% and 8.3-14.7%, respectively. The present enzyme immunoassay method could be applied to mass screening for congenital adrenal hyperplasia.View full abstractDownload PDF (834K) -
SHINICHI KAMACHI, KIYOSHIGE WAKABAYASHI, MASATOSHI YAMAGUCHI, YOSUKE O ...1983 Volume 31 Issue 8 Pages 2732-2736
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA sensitive spectrophotometric method for the assay of lipase in serum is described, based on the use of a chromogenic substrate, Orange I laurate. Orange I liberated from the substrate (used as an emulsion) under the optimal conditions for the enzyme reaction in the presence of sodium cholate (emulsifier of the substrate, activator of lipase, inhibitor of esterases) and sodium dodecyl sulfate (activator of lipase, inhibitor of esterases) is determined spectrophotometrically after adding concentrated sodium cholate to stop the enzyme reaction and to dissolve unreacted substrate, and diluting the mixture with water to reduce the absorbance due to the substrate. Serum lipase activities obtained by this method correlated well with those obtained by a method using olive oil as a substrate. The method is readily performed with good precision, and is suitable for the assay of many samples.View full abstractDownload PDF (558K) -
KAZUO OKUMURA, YOSHIHIRO KURODA, TOYOZO UNO1983 Volume 31 Issue 8 Pages 2737-2742
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of a red chromogen which is produced by applying the Fujiwara reaction to chloramphenicol was determined by means of NMR, mass spectroscopy and reasonance Raman spectroscopy. The red product was identified as 5-hydroxymethyl-4-(4-nitrobenzeno)-2, 3-pyrrolidindione. This compound is different from the nitrogenated polyene which is produced in the Fujiwara reaction applied to such gem-trichloro compounds as chloroform and benzotrichloride.View full abstractDownload PDF (555K) -
MASATSUNE ISHIGURO, TOSHIAKI NII, SADAOMI IMAMURA, SETSUO IMAMICHI, TO ...1983 Volume 31 Issue 8 Pages 2743-2750
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA high-molecular-weight glycoprotein which reacted with a specific antiserum to urinary human chorionic gonadotropin and with the gonadotropin receptor preparation from rat testes was detected in the extract of human chorionic tissues from the first trimester placenta of normal pregnancy and partially purified by ammonium sulfate fractionation followed by chromatographies on DEAE-Sephadex A-50 and Sephadex G-150. Its molecular weight was estimated to be 8.0×104 daltons by polyacrylamide gel disc electrophoresis in the presence of sodium dodecyl sulfate. In the presence of 2-mercaptoethanol, the major portion of this preparation was separated into alpha- and beta-subunits of rather high molecular weights compared to those of urinary human chorionic gonadotropin subunits by sodium dodecyl sulfate polyacrylamide gel disc electrophoresis. This preparation was shown to possess 2000 IU/mg of biological activity, and 2200 IU/mg of immunological activity, while its receptor binding capacity was equipotent to that of urinary chorionic gonadotropin. Chemical analyses, including amino acid and carbohydrate, were carried out. The present study suggests that high-molecular-weight type of human chorionic gonadotropin might be a complex of larger forms of alpha- and beta-subunits. This complex might be an intermediary component in the biosynthetic pathway of human chorionic gonadotropin or a product of posttranslational modification or a degradation product.View full abstractDownload PDF (814K) -
KEIZO HIRAHARA, TOYOYASU KUWAE, MUNETSUGU KURATA, TETSURO MATSUISHI, N ...1983 Volume 31 Issue 8 Pages 2751-2755
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe bacteriolytic action of human immunoglobulin G (IgG) and its modifications (pepsin-treated and sulfonated IgG) in the presence of complement was examined with K. pneumoniae and S. aureus. Lysis of K. pneumoniae was observed when concentrated IgG was added, while that of S. arueus was not. This lytic action against K. pneumoniae was unaffected by the above modifications of IgG. The results raise the possibility that IgG antibody an high concentration causes the lysis of K. penumoniae by activating the alternative pathway of the complement system and that such activation requires antibody specific to K. pneumonia.View full abstractDownload PDF (593K) -
TAKAFUMI WATANABE, TETSUYA SUGA1983 Volume 31 Issue 8 Pages 2756-2761
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of phytol on biochemical values (triglyceride and cholesterol levels of liver and serum, body weight gain and liver weight), and peroxisomal enzyme activities were investigated in rats. The rats were given phytol orally at the dose of 200 or 500 mg/kg body weight daily for 3 weeks. The triglyceride and cholesterol levels of the serum of the rats treated with phytol at 500mg/kg decreased by 32 and 35% respectively, while no influence on body weight gain or liver weight was observed. Fatty acyl-CoA oxidase activity and catalase activity in the livers of treated rats were increased by 29 and 20% at 200mg/kg, and by 36 and 44% at 500mg/kg, respectively. D-Amino acid oxidase activity was also increased by 54% (at 200mg/kg) and 85% (at 500mg/kg) in treated animals, but the activity of another peroxisomal enzyme, urate oxidase, did not change. On sucrose density gradient centrifugation of the light mitochondrial fractions prepared from the livers of control and treated rats, similar distribution patterns were observed in both samples, but the activities of catalase and fatty acyl-CoA oxidase of peroxisomal fraction of the treated (500mg/kg) group were increased by 68 and 45%, respectively. These results suggest that phytol might enhance peroxisomal β-oxidation and also induce some peroxisomal enzymes, causing change of peroxisomal enzyme compositions.View full abstractDownload PDF (586K) -
TAKAKO YOKOZAWA, PINGDONG ZHENG, HIKOKICHI OURA, MASAYUKI FUKASE, FUMI ...1983 Volume 31 Issue 8 Pages 2762-2768
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of the extract from Rhei Rhizoma was examined in rats with renal failure induced by an adenine diet. On treatment with the rhubarb extract, the level of urea nitrogen and creatinine in the serum showed a significant decrease, indicating an improvement of renal function. The urea concentrations in the liver and kidney were also decreased after the treatment. In addition, administration of the rhubarb extract to rats markedly decreased the kidney weight and 2, 8-dihydroxyadenine content in the kidneys. Macroscopic aspects of the kidneys, such as the appearance of the cut surface, were improved. However, there was no statistically significant difference between the control and rhubarb extract-treated groups with regard to the number of foreign body granulomas and deposits of acicular crystals (2, 8-dihydroxyadenine).View full abstractDownload PDF (1152K) -
KOHEI SAWAKI, RYO TAGUCHI, HIROH IKEZAWA1983 Volume 31 Issue 8 Pages 2769-2778
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interactions between phosphatidylinositol and membrane-bound enzymes in rat liver microsomes were studied by using phosphatidylinositol (PI)-specific phospholipase C of Bacillus thuringiensis and nonionic, anionic and cationic detergents. The dependence of activity of nucleoside diphosphatase on the detergent concentration varied with the detergents used. However, maximal activity with each detergent was attained within 30 min, and the enzyme activity was relatively stable during exposure to each detergent. When phosphatidylinositol in the microsomal membrane was hydrolyzed, the glucose-6-phosphatase activity was decreased in the presence of taurocholate. Nucleoside diphosphatase and 5'-nucleotidase were released by the breakdown of phosphatidylinositol in the membrane, while adenosine triphosphate (ATP) ase, reduced nicotinamide adenine dinucleotide (NADH)-cytochrome b5 reductase and carboxylesterase were not released. The pattern of release of nucleoside diphosphatase was significantly different from that of 5'-nucleotidase, and the release of the latter enzyme was greater than that of the former. Also, nucleoside diphosphatase was more extensively released from the microsomal membrane by treatment with taurocholate than with PI-specific phospholipase C, while the release of 5'-nucleotidase activity was greater on treatment with this phospholipase C than with taurocholate.View full abstractDownload PDF (929K) -
TETSUO SEKIYA, SATOSHI IMADA, SHUNSUKE HATA, SHUNICHI YAMADA1983 Volume 31 Issue 8 Pages 2779-2785
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure-activity relationships of thirty 2-(4-cinnamoyl-1-piperazinyl)-6, 7-dimethoxy-4-quinazolinamine derivatives for antihypertensive activity were analyzed by the adaptive least-squares (ALS) method. When the retention index (ΔRI) obtained from a C-18 reversed-phase column high-pressure liquid chromatography system was used as a lipophilic parameter, the discriminant equation L=-1.022ΔRI-2.560ΣσPh-1.966IPh(2-OR)+0.799 gave the best prediction, where L is the discriminant score, Σσph is the sum of the Hammett substituent constants of the substituents on the phenyl group and Iph(2-OR) is an indicator variable assigned a value of 1 for the presence of 2-alkoxy groups on the phenyl group. The effects of the lipophilicity and electronic character of substituents on the activity are discussed.View full abstractDownload PDF (703K) -
AKIRA TAKAMURA, FUMIYOSHI ISHII, SHUNICHI NORO, MASUMI KOISHI1983 Volume 31 Issue 8 Pages 2786-2792
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of the first pressure and/or number of passes through the homogenizer, and preagitation by an agitator, on the physical properties of emulsion bases were investigated. The first pressure of the homogenizer was varied in the range of 130 to 490kg/cm2, and the second pressure was kept constant at 60kg/cm2. Emulsifiers used were commercial grade Tween 80 and Span 20. Oil and water phases were liquid paraffin and distilled water, respectively. Emulsion stability was evaluated in terms of the following three physicochemical parameters : (1) particle diameter, (2) separation rate of water phase, (3) rheological properties of emulsion products. The following results were obtained. (1) With increases in agitation time and in intensity of agitation, the particle diameter of the emulsion became smaller. (2) The viscosity of emulsion prepared in the homogenizer increased remarkably with increase in the number of passes through the homogenizer. (3) The particle diameter of the emulsion was greatly decreased by the homogenizer only at the first pass. (4) Pre-agitation with an agitator is very useful for the preparation of emulsion products by means of a homogenizer.View full abstractDownload PDF (669K) -
TSUNEO UMEDA, ATSUKO MATSUZAWA, TERUYOSHI YOKOYAMA, KOJI KURODA, TSUTO ...1983 Volume 31 Issue 8 Pages 2793-2798
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMicroencapsulation of indomethacin (mc-IM) was carried out by using a gelatin. Sustained-release suppositories containing only mc-IM, and containing both mc-IM and intact IM were prepared by the fusion method. Plasma concentrations after rectal administration of the sustained-release suppository containing only mc-IM reached a plateau level and did not rise above 5μg/ml. No difference in bioavailability could be seen between this sustained-release suppository and the conventional suppository. The sustained-release suppository prepared by mixing mc-IM with intact IM rapidly gave a desirable plasma concentration and maintained an effective plasma level of the drug for a considerable period of time, that is, the maximal plasma concentration (Cmax) was below 5μg/ml and the time for which a plasma level above 2μg/ml was maintained was 6h. On the basis of these results, the combined dosage form should represent a convenient therapy with reduced risk of side-effects and reduced frequency of administration.View full abstractDownload PDF (610K) -
MINEZO OTSUKA, SATOSHI FURUUCHI, SHOICHI HARIGAYA1983 Volume 31 Issue 8 Pages 2799-2809
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe formation route of the sulfur-containing metabolites of afloqualone [6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone, AFQ], a centrally acting muscle relaxant, was studied in rats. When 14C-N-acetyl AFQ 2-mercapturate (AFQM) methyl ester was administered orally to normal rats, it was excreted in the bile as AFQM, one of the major biliary metabolites of AFQ, and in the urine as sulfur-containing metabolites of AFQ such as methylsulfinyl and methylsulfonyl metabolites of AFQ. This indicated that AFQM was a precursor of these methylsulfinyl and -sulfonyl metabolites. Pretreatment of rats with antibiotics significantly reduced the urinary excretion of 14C-AFQM and its metabolites as compared with normal rats. Oral administration of 14C-AFQ to antibiotics-treated rats also significantly reduced the amounts of the sulfur-containing metabolites excreted into the urine, but did not affect the amounts of other non-sulfur-containing metabolites. In addition, oral administration of 14C-AFQ to bile-duct-ligated rats gave results similar to those in the antibiotics-treated rats. These results indicate that in normal rats microfloral metabolism is necessary for the formation of the methylsulfinyl and -sulfonyl metabolites from AFQM and other unidentified mercapturate pathway conjugates excreted into the bile. The metabolites of AFQ produced by the microflora are reabsorbed into the systemic circulation, processed by further metabolism in the liver, and in turn excreted in the urine.View full abstractDownload PDF (928K) -
KUNIYOSHI TANAKA, KEIZO MATSUO, AI NAKANISHI, TOSHIKO HATANO, HISAKO I ...1983 Volume 31 Issue 8 Pages 2810-2819
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn the basis of the generally accepted view that copper ions take part in the occurrence of inflammation, hydroxamic acids and acid hydrazides derived from various substituted cinnamic acids and hydrocinnamic acids, which were expected to chelate with copper ions, were synthesized and evaluated for anti-inflammatory activity by the carrageenin-induced rat paw edema assay and for analgesic activity by the phenylquinone writhing method in mice. Some of the synthesized compounds exhibited both activities, and 3-(3, 4-dimethoxyphenyl)propiohydroxamic acid and its Zn complex were more active than aspirin. The Cu (II) complexes of hydroxamic acid derivatives were synthesized and were assumed to have polymeric structures from the results of elemental analysis, molecular weight measurement and determination of magnetic susceptibility.View full abstractDownload PDF (920K) -
ATSUKO NISHIYAMA, HIDEO ETO, YUKIMASA TERADA, MASANOBU IGUCHI, SHOSUKE ...1983 Volume 31 Issue 8 Pages 2820-2833
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-Allyl-2, 6-dimethoxyphenol and related compounds have been subjected to anodic oxidation to afford a number of oxidation products including asatone-type neolignans, heterotropanone-type compounds and arylpropanoids. Furthermore, the formation processes of these oxidation products are shown to involve both radical and cationic reactions which are dependent upon the applied potentials, solvent media and substituents on the aromatic ring.View full abstractDownload PDF (1285K) -
ATSUKO NISHIYAMA, HIDEO ETO, YUKIMASA TERADA, MASANOBU IGUCHI, SHOSUKE ...1983 Volume 31 Issue 8 Pages 2834-2844
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSome propenylphenols have been subjected to anodic oxidation to afford a number of oxidation products including arylpropanoid-, asatone-, austrobailignan-, carpanone- and licarin-type neolignans. The formation process of these compounds involves both radical and cationic reactions controlled by the applied potentials, solvent media and substituents on the aromatic rings.View full abstractDownload PDF (1141K) -
ATSUKO NISHIYAMA, HIDEO ETO, YUKIMASA TERADA, MASANOBU IGUCHI, SHOSUKE ...1983 Volume 31 Issue 8 Pages 2845-2852
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnodic oxidation of 4-hydroxycinnamic acids, 4-hydroxycinnamamides and related phenols was carried out at a controlled potential, using an undivided cell, to afford the corresponding asatone-, isoasatone-, pinoresinol- or podophyllotoxin-type compounds. Furthermore, the corresponding dihydroxy compounds were also electrolyzed at a controlled potential to give different dienones depending on the side chains.View full abstractDownload PDF (812K) -
ATSUKO NISHIYAMA, HIDEO ETO, MASANOBU IGUCHI, SHOSUKE YAMAMURA1983 Volume 31 Issue 8 Pages 2853-2858
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTriacetic lactone, 4-hydroxycoumarins and 2-chloromethyl-5-hydroxy-4-pyrone were subjected to anodic oxidation in methanol containing LiClO4 or NaCN to afford the corresponding methoxy or cyano compounds. In basic media, however, bispyrone and biscoumarol were produced from triacetic lactone (4-hydroxy-6-methyl-2-pyrone) and 4-hydroxycoumarin, respectively. The formation processes of these oxidation products are discussed.View full abstractDownload PDF (647K) -
YOSHIAKI SHIRATAKI, MASAAKI ENDO, ICHIRO YOKOE, MANKI KOMATSU1983 Volume 31 Issue 8 Pages 2859-2863
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new chromone, named sophorachromone A (I), mp 138-139°C, C19H22O4, and a new flavanone, named sophoraflavanone A (II), mp 144-145°C, C25H28O5, were isolated together with isosophoranone (III) from the root of Sophora tomentosa L. (Leguminosae). The structures of I and II were established to be 8-geranyl-5, 7-dihydroxychromone and 6-geranyl-5, 7, 4'-trihydroxyflavanone, respectively, on the basis of chemical and spectral evidence.View full abstractDownload PDF (522K) -
TOSHIHIKO OZAWA, TAKAO KWAN1983 Volume 31 Issue 8 Pages 2864-2867
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe ClO2 radical was obtained from many reaction systems (Ti3+-NaClO3, Ti3+-NaClO2 and H2SO4-NaClO2) in aqueous solutions. The formation of the ClO2 radical was detected by means of the rapid-mixing flow technique coupled with electron spin resonance (ESR) measurements.View full abstractDownload PDF (448K) -
HIDEAKI SASAKI, TOKUJIRO KITAGAWA1983 Volume 31 Issue 8 Pages 2868-2878
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBis (2-isocyano-2-tosylethyl) benzenes (12a, 12b, and 12c), synthesized by the reaction of tosylmethyl isocyanide (7) with bis (bromomethyl) benzenes (11a, 11b, and 11c) in 2 : 1 molar ratio, reacted again with 11a, 11b, and 11c under phase-transfer conditions to form 2, 11-diisocyano-2, 11-ditosyl[32]cyclophanes of ortho, meta, and para types (14, 15, and 17), 2, 11, 20-triisocyano-2, 11, 20-tritosyl[33]paracyclophane (19), and 2, 11, 20, 29-tetratosyl[34]cyclophanes of meta and para types (16 and 18). [32]Metacyclophane (1), [33]paracyclophane (31), and [34]meta- and paracyclophanes (32 and 33) could be obtained by hydrolysis and Wolff-Kishner reduction of the above intermediates (15, 16, 18, and 19). Hydrolysis of 2, 11-diisocyano-2, 11-ditosyl[32]orthocyclophane (14) yielded 5, 6, 11, 12-tetrahydro-dibenz[b, g]-azulen-5-one (30) instead of the corresponding ketone (26). Structural properties of the prepared cyclophanes (15, 17, 21, 23, 24, 31, and 33) are described on the basis of the proton magnetic resonance (PMR) spectra.View full abstractDownload PDF (863K) -
Studies on the Constituents of the Plants of Illicium Species. II. Structures of Phenolic ComponentsKENICHI YAKUSHIJIN, TOMOKO TOHSHIMA, RIKA SUZUKI, HIROYUKI MURATA, SHE ...1983 Volume 31 Issue 8 Pages 2879-2883
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTen phenolic compounds were isolated from leaves or timber of Illiciaceous plants, Illicium tashiroi MAXIM., I. arborescens HAYATA, and I. anisatum L., and their structures were determined 1-10 by spectroscopic and synthetic studies. Of the ten, 4-allyl-5-(3-methylbut-2-enyloxy)-1, 2-methylenedioxybenzene (7), 4-allyl-2-methoxy-6-(3-methyl-2-butenyl)phenol (9), and 4-allyl-2, 6-dimethoxy-3-(3-methyl-2-butenyl)phenol (10) are new compounds.View full abstractDownload PDF (563K) -
TAKAO MORI, HIDEO BANDO, YOSHIO KANAIWA, KOJI WADA, TAKASHI AMIYA1983 Volume 31 Issue 8 Pages 2884-2886
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new diterpene alkaloid, deoxyjesaconitine, was isolated from the rhizoma of Aconitum subcuneatum NAKAI (Ranunculaceae) and its structure was established by analysis of the spectral data and by conversion of jesaconitine into deoxyjesaconitine. Deoxyaconitine, hypaconitine, jesaconitine, aconitine, and mesaconitine were also isolated from the same plant.View full abstractDownload PDF (417K) -
MASASHIGE YAMAUCHI, SADAMU KATAYAMA, TOSHIO WATANABE1983 Volume 31 Issue 8 Pages 2887-2891
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMichael condensation of 2-methylsulfinylmethyl-1, 3-dicarbonyl compounds (3) or 2-methylene-1, 3-dicarbonyl compounds (4) with 4-hydroxycoumarin (5) at ambient temperature gave 2-[(4-hydroxycoumarin-3-yl)methyl]-1, 3-dicarbonyl compounds (6). Treatment of 6 with methanolic hydrogen chloride resulted in the regioselective formation of 2, 2, 3-trisubstituted-3, 4-dihydro-2H-pyrano[3, 2-c][1]benzopyran-5-ones.View full abstractDownload PDF (446K) -
MASATO KASHIMURA, YASUO KIKUGAWA1983 Volume 31 Issue 8 Pages 2892-2894
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFormylation of indoles was carried out in formic acid. 3-Unsubstituted indoles were formylated preferentially at C-3 and 3-substituted indoles were formylated at N-1 ; C-2 was not formylated in either case.View full abstractDownload PDF (377K) -
YUJI SUZUKI, HIROSHI TAKAHASHI1983 Volume 31 Issue 8 Pages 2895-2898
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of (E)-(S)-N-(1-isopropyl-2-methoxyethyl)benzylideneamine (2) with ethylmagnesium bromide gave a mixture of (1S, 1'S)- and (1R, 1'S)-N-(1'-isopropyl-2'-methoxyethyl)-1-phenylpropylamines (3) (91 : 9%). (E)-(S)-N-(1-Isopropyl-2-methoxyethyl)propylideneamine (5) was treated with phenyllithium to give (1R, 1'S)- and (1S, 1'S)-3 (95 : 5%). On the other hand, reaction of (E)-(S)-N-(2-hydroxy-1-isopropylethyl)benzylideneamine (6) with ethylmagnesium bromide yielded a mixture of (1S, 1'S)- and (1R, 1'S)-N-(2'-hydroxy-1'-isopropylethyl)-1-phenylpropylamines (7) (78 : 22%). The absolute configurations of these amines were determined by circular dichroism (CD) spectroscopy and comparison with authentic samples synthesized by alternative methods.View full abstractDownload PDF (542K) -
NOBUYA KATAGIRI, RYUJI NIWA, TETSUZO KATO1983 Volume 31 Issue 8 Pages 2899-2904
Published: August 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of dichloroketene with ethyl N-(2-pyridyl)formimidates (1) gave ethyl 2, 2-dichloro-3-ethoxy-3-(2-pyridylamino)propionates (3) and 3-chloro-2-ethoxypyrido[1, 2-a]pyrimidin-4(4H)-ones (4), together with 3, 3-dichloro-4-ethoxy-1-(2-pyridyl)-2-azetidinone (2). Compound 3b, on standing at room temperature, was transformed into ethyl 2-ethoxy-8-methylimidazo[1, 2-a]pyridine-3-carboxylate (6).View full abstractDownload PDF (631K)