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SATOSHI TAKATA, YUKIO ONO, YO UEDA
1985 Volume 33 Issue 8 Pages
3077-3091
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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The extension of the CNDO/S calculation to aromatic and heterocyclic compounds containing Si, P, S or Cl was investigated in detail. Parameters of the second-row elements were optimized by using as many types of compound as possible. The spd basis sets were shown to be superior to the sp basis sets in the calculated transition energies but also orbital energies coincide very well with observed values without exception. The method presented in this work is expected to be widely applicable to the calculation of the electronic states of many aromatic and heterocyclic compounds containing second-row elements.
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SETSUO SAITO, TAKESHI KATO, YUTAKA MORITA, HIROSHI MIYAMAE
1985 Volume 33 Issue 8 Pages
3092-3095
Published: August 25, 1985
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The title compound, C
22H
22NO
3P, crystallizes in space group P2
1, with a=13.219 (8), b=10.536 (7), c=7.143 (4) A, β=94.87 (6), and Z=2. The structure was solved by the direct method and refined to an R value of 0.0353. A unique structure having a cyclobutane ring fused with a furanoside moiety, and a diphenylphosphine group at the ring juncture, was confirmed by the analysis. A 270 MHz proton nuclear magnetic resonance (
1H-NMR) analysis of the compound showed interesting coupling features of the cyclobutane ring protons and phosphorus.
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JUNICHI UEDA, AKIRA HANAKI, NAOKO YOSHIDA, TERUMI NAKAJIMA
1985 Volume 33 Issue 8 Pages
3096-3100
Published: August 25, 1985
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A proton nuclear magnetic resonance (
1H-NMR) study of the interaction of Zn (II) ion with histidine-containing peptide, L-histidylglycylglycine (his-gly-gly), was carried out. The 1 : 2 complex of Zn (II)-(his-gly-gly) takes different coordination structures depending on the pH. In the region of pH 4.5-6.5, the complex is a tautomer in which the Zn (II) ion is exchanged dynamically among amide carbonyl oxygen, imidazole nitrogen, and amino nitrogens above pH 6.5.
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HIROFUMI TAKEUCHI, YOSHIHISA MIWA, SHUSHI MORITA, JUTARO OKADA
1985 Volume 33 Issue 8 Pages
3101-3106
Published: August 25, 1985
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An improved Williamson ether synthesis was conducted under phase-transfer conditions by using a polymer-supported quaternary salt. Benzyl butyl ether was produced from benzyl alcohol and butyl bromide, and it was shown that the rate of reaction was influenced by the concentrations of benzyl alcohol and butyl bromide in the organic phase and the concentration of KOH in the aqueous phase. Based on kinetic studies, the rate-determining step was found to depend on the concentrations of the reactants. The content of water in the organic phase, which increased with the concentration of benzyl alcohol, was found to be closely related to the decrease in the rate of raction.
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HIROSHI HARA, RYUICHI SHIRAI, OSAMU HOSHINO, BUNSUKE UMEZAWA
1985 Volume 33 Issue 8 Pages
3107-3112
Published: August 25, 1985
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Four 4-phenyl-1, 2, 3, 4-tetrahydroisoquinolines (8b, c, f, g) were prepared from two simple synthons, styrene oxide and the benzylamines (2b-e), via the β-hydroxyphenethylamines (3b-e) in high yield. On the other hand, the β-methoxyphenethyl methanesulfonate (16), obtained from 4-benzyloxystyrene oxide (11), was coupled with the benzylamine (2a) to give the N-benzyl-β-methoxyphenethylamine (17). A facile total synthesis of (±)-cherylline (1) was accomplished by acid treatment of 17.4'-O-Methylcherylline (18) was also synthesized through the same pathway.
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TOMOHISA NAGAMATSU, MASAYOSHI UKAI, FUMIO YONEDA, DESMOND J. BROWN
1985 Volume 33 Issue 8 Pages
3113-3121
Published: August 25, 1985
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4-Methyl-s-triazolo [4, 3-a] purin-9 (4H)-ones (IV) were synthesized by the condensation of 2-hydrazino-3-methylpurin-6 (3H)-ones (III), which were derived from the reaction of 3-methyl-2-thioxanthines (II) with hydrazine hydrate, with appropriate ortho esters. 7-Aryl-4-methyl-s-triazolo [4, 3-a] purin-9 (4H)-ones (VI) were synthesized by the oxidative cyclization of 2-arylidenehydrazino-3-methylpurin-6 (3H)-ones (V), which were derived from the reaction of III with appropriate benzaldehydes, with diethyl azodicarboxylate (DAD) or with air in glacial acetic acid. 7-Mercapto-4-methyl-s-triazolo [4, 3-a] purin-9 (4H)-ones (VII) were also prepared in a manner similar to that used for III, but using carbon disulfide, and VII were further converted into the corresponding 7-alkylthio derivatives VIII by alkylation. The treatment of III with nitrous acid afforded the corresponding 4-methyltetrazolo [1, 5-a] purin-9 (4H)-ones (IX).
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JEAN-CHARLES LANCELOT, DANIEL LADUREE, MAX ROBBA
1985 Volume 33 Issue 8 Pages
3122-3128
Published: August 25, 1985
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The synthesis of 5, 6-dihydro 6-oxo pyrido [2, 3-e] pyrrolo [1, 2-a] pyrazine, and 5, 6-dihydro 6-oxo pyrazino [2, 3-e] pyrrolo [1, 2-a] pyrazine is described. The starting materials, 3-amino pyridine and 3-amino pyrazine are converted into pyrrolyl derivatives using 2, 5-dimethoxytetrahydrofuran in glacial acetic acid. Subsequent cyclizations of these latter afforded the title compounds. Proton nuclear magnetic resonance spectra are studied.
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YOSHINORI FUJIMOTO, TAKETOSHI YAMADA, NOBUO IKEKAWA
1985 Volume 33 Issue 8 Pages
3129-3133
Published: August 25, 1985
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The utility of the proton nuclear magnetic resonance method involving pyridine-induced deshielding was demonstrated for stereochemical assignment at the C-6 position of sterols having a 5α, 6ζ-diol moiety. Thus, the 4α-hydrogen resonance of 6α-isomers such as cholest-7-ene-3β, 5α, 6α-triol (8) is observed at ca. 3.0 ppm, whereas the 4β-hydrogen resonance of 6β-isomers such as cholest-7-ene-3β, 5α, 6β-triol (10) is observed at ca. 3.0 ppm. This method was applied to a marine sterol (4) isolated from a sponge, Dysidea sp., and it was concluded that the structure should be revised to the 6α-isomer (5) rather than the reported 6β-isomer (4).
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HIROSHI TAKAHASHI, YUMIKO KUBOTA, MIEKO IGUCHI, MASAYUKI ONDA
1985 Volume 33 Issue 8 Pages
3134-3141
Published: August 25, 1985
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The effects of 5-substituents on sodium borohydride reduction of flavanonols have been examined. The bulk of substituents governs the stereochemistry of reduction, and particularly, the acetoxy group gives an interesting result accompanied by over-reduction. In addition, the 5-acetoxy group plays an improtant role in the stereochemistry of the newly introduced 4-oxygen functions in hydrolysis of (±)-fistacacidin acetates.
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FENGLIN HSU, GENICHIRO NONAKA, ITSUO NISHIOKA
1985 Volume 33 Issue 8 Pages
3142-3152
Published: August 25, 1985
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Together with propelargonidin dimers (14, 15 and 16), and procyanidin trimers (23, 24 and 25) of common types, two novel proanthocyanidin dimers, kandelins A-1 (12) and A-2 (13), and four trimers, kandelins B-1 (19), B-2 (20), B-3 (21) and B-4 (22), which all contain a phenylpropanoid substituent in the upper flavan unit, have been isolated from the bark of Kandelia candel (L.) DRUCE (Rhizophoraceae). Spectroscopic evidence combined with chemical studies involving acid-catalyzed thiolytic degradation permitted the assignment of their structures. The presence in this plant source of flavan-3-ols, (+)-afzelechin (2), (+)-catechin (3), (-)-epicatechin (4) and (+)-gallocatechin (5), known proanthocyanidins B-1 (8), B-2 (9), C-1 (17) and trimer (18), and cinchonains Ia (6), Ib (7), IIa (10) and IIb (11) was also demonstrated.
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EIKO OHTSUKA, SHIGENORI IWAI, TOMOKO TOKUNAGA, MORIO IKEHARA
1985 Volume 33 Issue 8 Pages
3153-3159
Published: August 25, 1985
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To investigate the efficiency of expression of synthetic genes, deoxyribonucleic acid (DNA) duplexes (33-37 base pairs) containing the ribosome binding site (S.D. sequence) for trpL and appropriate termini were synthesized. This involved chemical synthesis of 8 oligonucleotides with chain lengths of 16-19 by the solid-phase phosphotriester method followed by enzymatic joining with DNA ligase. The duplexes were designed to replace a restriction fragment from a plasmid containing the trp promoter and a synthetic human growth hormone gene. The S.D. sequence in these duplexes was located upstream from a Cla I site to make a distance of 9, 11 or 13 bases from the initiation signal (ATG).
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SUSUMU KAMATA, NOBUHIRO HAGA, TAKEAKI MATSUI, WATARU NAGATA
1985 Volume 33 Issue 8 Pages
3160-3175
Published: August 25, 1985
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Several 5-fluorouracil derivatives in which the phthalidyl (1, 3-dihydro-3-oxoisobenzofuran-1-yl) group, appropriately substituted on its benzene ring, is substituted at the N (1)-or N (3)-position or at both positions were synthesized, and their antitumor activities were evaluated. Among these compounds, 1-(1, 3-dihydro-3-oxoisobenzofuran-1-yl)-5-fluorouracil (3a, 590-S) was shown to be markedly active against several experimental tumor systems. Several methods for a simple and efficient large-scale preparation of 3a were examined. The large-scale preparation of 3a was effected most efficiently by the condensation of 5-fluorouracil with the quaternary ammonium salt of 3-bromophthalide in the presence of a base. The synthesis of (+)- and (-)-3a is also described.
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HARUHISA KIZU, MICHIYO KOSHIJIMA, TSUYOSHI TOMIMORI
1985 Volume 33 Issue 8 Pages
3176-3181
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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On the basis of chemical and physicochemical evidence, the structures of four dammarane triterpene glycosides, named Kizuta saponins K
7A (I), K
7B (VII), K
9 (X) and K
13 (XII), which were isolated from the stem and bark of Hedera rhombea BEAN (Araliaceae), were established as follows : I, 3-oxo-20 (S)-dammar-24-ene-6α, 20, 21, 26-tetraol 26-O-β-D-glucopyranoside ; VII, 20 (S)-dammar-24-ene-3β, 6α, 20, 21, 26-pentaol 26-O-β-D-glucopyranoside ; X, 20 (S)-dammar-24-ene-3β, 6α, 20, 26-tetraol 3, 26-di-O-β-D-glucopyranoside ; XII, 20 (S)-dammar-24-ene-3β, 6α, 20, 26-tetraol 3-O-β-sophoroside-26-O-β-D-glucopyranoside.
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HIROSHI MORIMOTO, KUNIKO KURIMOTO, ISUKE IMADA
1985 Volume 33 Issue 8 Pages
3182-3186
Published: August 25, 1985
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Ubiquinone-2 (1) was oxidized to 6-[7-carboxy-3-methyl- (2E, 6E)-2, 6-octadienyl]-2, 3-dimethoxy-5-methyl-1, 4-benzoquinone (2) and 6-[6, 7-dihydroxy-3, 7-dimethyl- (E)-2-octenyl]-2, 3-dimethoxy-5-methyl-1, 4-benzoquinone (3) by the 6000×g supernatant of guinea-pig liver homogenate in the presence of nicotinamide-adenine dinucleotide (NAD)- and dihydronicotinamideadenine dinucleotide phosphate (NADPH)-generating systems.
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YOSHIHISA SHIBANUMA, TOSHIHIKO OKAMOTO
1985 Volume 33 Issue 8 Pages
3187-3194
Published: August 25, 1985
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A synthetic study was carried out on the 1-azabicyclo [2.2.1] heptane partial structure (D/E ring system) of an aconite alkaloid, kobusine. A 1-azabicyclo [2.2.1] heptane system, (±)-6, 15, 16-iminopodocarpane-8, 11, 13-triene (3), was synthesized from the 4a-nitromethylhydrophenanthrone (7), which was obtained from the tetrahydrophenanthol (4) through an abnormal Reimer-Tiemann reaction. The bridged nitrogen structure was formed from the bicyclic chloramine (23) by means of the Hofmann-Loffler reaction. The structure of 3 was confirmed by X-ray diffraction analysis.
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TOSHIO FUKAI, YOSHIO HANO, KAZUHIRO HIRAKURA, TARO NOMURA, JUN UZAWA, ...
1985 Volume 33 Issue 8 Pages
3195-3204
Published: August 25, 1985
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Two novel 2-arylbenzofuran derivatives named mulberrofurans F and G (=albanol A), as well as albanol B (3), were isolated from the ethyl acetate extract of the root bark of cultivated mulberry tree (Japanese name "Roso, " a cultivated variety of Morus lhou KOIDZ.). The structures of mulberrofurans F and G were shown to be 1 and 2, respectively, on the basis of spectral and chemical evidence. Mulberrofurans F (1) and G (2) were derived from chalcomoracin (4) and mulberrofuran C (5), respectively, by photocyclization in acidic solution. The compounds (1, 2, and 3) are optically active and can be regarded biogenetically as variations of Diels-Alder type adducts of chalcone derivatives and a dehydroprenyl-2-arylbenzofuran derivative. Intravenous injection of mulberrofuran F (1), as well as G (2), caused a marked depressor effect in rabbit.
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SHINYA KIYAMA, KOUKI KITAGAWA, TADASHI AKITA, WILLIAM Y. CHEY, AVIDIN ...
1985 Volume 33 Issue 8 Pages
3205-3217
Published: August 25, 1985
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Porcine secretin was synthesized by the trifluoromethanesulfonic acid deprotecting procedure. Release of the biologically important His
1-residue from synthetic secretin was noted when the secretin was incubated in an aqueous solution at 37°C under nearly neutral conditions. Apparent autolysis of the N-terminal tetrapeptide, His-Ser-Asp-Gly, was examined by using 5 peptide analogs, and the participation of the β-carboxyl group of Asp and the basic amino acid, His, in this unusual phenomenon was deduced. Hydrolysis of the peptide bonds between Asp-Ser (15-16) and Asp-Gly (3-4) was also noted when the above incubated solution was examined by high performance liquid chromatography.
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HITOSHI TANAKA, ICHIRO KATO, KAZUO ITO
1985 Volume 33 Issue 8 Pages
3218-3223
Published: August 25, 1985
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The coumarinolignoid cleomiscosin A (1), having antitumor activity, has been synthesized via the keto-ester (10), which was prepared from readily available starting materials (6 and 9). Removal of the methoxymethyl group of 10 followed by reduction with lithium borohydride gave a mixture of diols (12a, b). Treatment of 12a, b with 5% sulfuric acid in acetic acid provided cleomiscosin A monoacetate (14) and subsequent hydrolysis with sodium hydroxide afforded 1.
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HIDETOSHI TAKAGI, TOHRU HAYAKAWA, TOSHIAKI MIURA, MICHIYA KIMURA
1985 Volume 33 Issue 8 Pages
3224-3230
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Dissolution of 17α-hydroxyprogesterone (1) in 80% sulfuric acid gave two D-homosteroids through C (13)-C (17) bond migration, 17aβ-hydroxy-17aα-methyl-D-homoandrost-4-ene-3, 17-dione (2) and 17a-methylene-D-homoandrost-4-ene-3, 17-dione (3), in 53 and 9% yields, respectively. The latter product was also obtained in 73% yield from the reaction of 1 with 90% sulfuric acid. Proton nuclear magnetic resonance (
1H-NMR) studies of the acid solutions revealed that the D-homoannulation of 1 to 2 occurs rapidly even in 80 or 90% sulfuric acid, and that 2 is dehydrated rapidly to 3 in 90% sulfuric acid. The D-homoannulation was demonstrated to be an initial step in the color and fluorescence reaction of 1 with sulfuric acid.
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LI WU, TOSHIO MIYASE, AKIRA UENO, MASANORI KUROYANAGI, TADATAKA NORO, ...
1985 Volume 33 Issue 8 Pages
3231-3236
Published: August 25, 1985
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Two flavanones, kushenol A (1) and kushenol B (2), one flavonol, kushenol C (3), one chalcone, kushenol D (4), and one pterocarpan, kushenin (5), were isolated from the dry roots of Sophora flavescens AITON (Leguminosae). Their structures were elucidated on the basis of elemental analyses and spectral data.
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AKIHIKO ISHIDA, TOHRU NAKAMURA, KUNIHIKO IRIE, TOKURO OHISHI
1985 Volume 33 Issue 8 Pages
3237-3249
Published: August 25, 1985
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N-Alkylthiocarbonyltryptophan (2a-i) and tryptamine (2j-m) derivatives can be converted into the corresponding 3, 4-dihydro-β-carbolines (3) under mild conditions by the use of alkylating or acylating agents. The NaBH
4 reduction of 1, 3-disubstituted 3, 4-dihydro-β-carbolines (3a-i) gave cis- (5) or trans-1, 2, 3, 4-tetrahydro-β-carbolines (6) with satisfactory stereoselectivity. The synthesis of optically active 3a, b and 5a, b is also described.
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JUNKO MATSUMOTO, TOMOKO FUJIMOTO, CHIE TAKINO, MASAHITO SAITOH, YOSHIO ...
1985 Volume 33 Issue 8 Pages
3250-3256
Published: August 25, 1985
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Two new isoprenylated flavonols, broussoflavonols A and B, and two isoprenylated chalcones, broussochalcones A and B, were isolated from the benzene extract of the cortex of Broussonetia papyrifera (L.) VENT. (Japanese name "Kajinoki, " Moraceae). The structures of broussoflavonols A, B, and broussochalcone B were shown to be 1, 2, and 4, respectively, on the basis of spectral evidence, and the structure of broussochalcone A was determined to be 3 on the basis of spectral and chemical evidence.
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YASUMITSU TAMURA, TERUHISA TSUGOSHI, SHINICHIRO MOHRI, YUKO NAKAJIMA, ...
1985 Volume 33 Issue 8 Pages
3257-3262
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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A novel synthesis of alkyl 2-alkoxycarbonyl-3-pyridineacetates (2), alkyl 3-alkoxycarbonyl-4-pyrazoleacetate (5), and alkyl 5-alkoxycarbonyl-4-(1, 2, 3-triazole) acetate (6) is described. Diels-Alder reaction of 1, 3-dialkoxycarbonylallenes (3) with 1-azadiene systems (4) gave 2, and 1, 3-dipolar cycloaddition of 3 to diazoalkanes and trimethylsilylazide gave 5 and 6, respectively. The structures of the cycloadducts and the regiochemistry of the cycloadditions are discussed.
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TOHRU UEDA, YUJI NOMOTO, AKIRA MATSUDA
1985 Volume 33 Issue 8 Pages
3263-3270
Published: August 25, 1985
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Synthesis of 8-alkyladenosines and related nucleosides is described. Treatment of 5'-O-acetyl-2', 3'-O-isopropylidene-8-methylsulfonyladenosine with ethyl sodioacetoacetate gave the 8-ethoxy-carbonylmethyl derivative (1). Hydrolytic decarboxylation of 1 followed by deacetonation afforded 8-methyladenosine (2) in high yield. Alkylation of 1 with methyl or ethyl iodide followed by hydrolytic decarboxylation afforded 8-ethyl- and 8-propyladenosines, respectively. Attempts at dimethylation of the 8-methylene group of 1 resulted in the formation of the N
6-dimethyladenosine derivative. Selective dimethylation of the amino groups of 2'-deoxyadenosine and 2'-deoxycytidine has been accomplished by using a combination of methyl iodide and sodium hydride without methylation of the sugar hydroxyl groups of these nucleosides. 8, 2'-Anhydro-9-β-D-arabinofuranosyl-8-hydroxymethyladenine was prepared from a 8-cyanoadenosine derivative by the procedure involving anhydro-bond formation by base treatment of 8-hydroxymethyl-2'-Otosyladenosine. The circular dichroism spectral characteristics of 8-alkyladenosines are discussed.
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HIROTERU SAYO, TAKASHI MICHIDA
1985 Volume 33 Issue 8 Pages
3271-3278
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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The paramagnetic species formed by in situ electrochemical oxidation of eleven N-(o-nitrophenylthio) alicyclic amines in acetonitrile or propionitrile have been identified as the radical cations derived from the parent sulfenamides by one-electron transfer. The observed non-equivalence of the two N-methylene groups indicated the existence of restricted rotation around the S-N bond and three-electron π-bonded geometry. As regards the radical cations derived from six-membered alicyclic sulfenamides, the ring inversion was apparently conformationally frozen on the electron spin resonance (ESR) time scale even at 25°C. Based on the ESR and nuclear magnetic resonance data it is proposed that the C
2N-S group in these radical cations is pyramidal and that the nitrogen inversion of these radicals is slow on the ESR time scale. The stability of the radical cations is discussed.
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MASAZUMI IKEDA, TAKAMASA UCHINO, MASAMI TAKAHASHI, HIROYUKI ISHIBASHI, ...
1985 Volume 33 Issue 8 Pages
3279-3286
Published: August 25, 1985
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Photoirradiation of 2-[N-acyl-N-(2-propenyl) amino] cyclohex-2-enones gave the 9-acyl-9-azatricyclo [5.2.1.0
1.6] decan-2-ones as the major products. In some cases, 1-acetyl-1, 4, 4a, 5, 6, 7, 8, 8a-octahydroquinol-8-one, 1-benzoyl-3-vinyl-2, 3, 3a, 4, 5, 6, 7, 7a-octahydroindol-7-one, and 1-(2-propenyl)-1-azaspiro [3.5] nonane-2, 5-dione were isolated and characterized as minor products.
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TAKUSHI KURIHARA, KAYOKO KAWAMURA, RYUJI YONEDA
1985 Volume 33 Issue 8 Pages
3287-3292
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Reaction of 1-methyl- or 1-benzyl-9-phenyl-1, 2, 3, 4-tetrahydro-9H-indeno [2, 1-b] pyridin-4-ones (1a and 1b) with potassium hydroxide in 1-propanol gave the 9-hydroxy derivatives (4a and 4b) in good yield. Sodium borohydride reduction of 4a gave the B/C-cis-4, 9-dihydroxy-1, 2, 3, 4, 4a, 9a-hexahydro-9H-indeno [2, 1-b] pyridine (8) stereospecifically. On the other hand, 4b gave the B/C-trans-4, 9-dihydroxy-1, 2, 3, 4, 4a, 9a-hexahydro-9H-indeno [2, 1-b] pyridine (10) and its C-9 isomer (11). Treatment of 11 with acetic anhydride in pyridine gave the corresponding monoacetate 13. However, acetylation of 10 afforded the B/C-cis monoacetate 12 with isomerization at B/C ring juncture. The structure and stereochemistry of these compounds is discussed.
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FENGLIN HSU, GENICHIRO NONAKA, ITSUO NISHIOKA
1985 Volume 33 Issue 8 Pages
3293-3298
Published: August 25, 1985
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Dimeric, trimeric and tetrameric procyanidins have been isolated, together with (+)-catechin (1) and (-)-epicatechin (2), from the tubers of Dioscorea cirrhosa LOUR. (Dioscoreaceae). By comparisons of the physical and spectral data, the dimers (3-5), trimers (6-8) and tetramer (9) were identified as procyanidins obtained previously. The structures of two other trimers (10 and 11) were established by acid-catalyzed thiolytic degradation, while the formation of the tetramer (12) by condensation of the 4-carbocation of 1 with 6, in conjunction with
1H- and
13C-nuclear magnetic resonance examinations, established the structure of 12.
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NOBUO IKOTA, HISANARI SHIBATA, KENJI KOGA
1985 Volume 33 Issue 8 Pages
3299-3306
Published: August 25, 1985
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A chiral carbapenam ring system ((3R, 5R)-(+)-19 and -20) having the desired absolute configuration at C-5 was synthesized starting from (S)-aspartic acid, and the latter product was further transformed to a chiral carbapenem derivative ((5S, 2'R)-(+)-21) having an (R)-cysteine moiety as a side chain.
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KOUKI KITAGAWA, KUNIO YONETO, SHINYA KIYAMA, KENSHI ANDO, TATSUHIKO KA ...
1985 Volume 33 Issue 8 Pages
3307-3316
Published: August 25, 1985
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The docosapeptide corresponding to the entire amino acid sequence of canine motilin, a newly characterized gastric motor activity-stimulating polypeptide, was synthesized by the conventional solution method. All protecting groups employed were removed by 1 M trifluoromethanesulfonic acid-thioanisole-trifluoroacetic acid and the deprotected peptide was purified by gel-filtration on Sephadex G-25, followed by partition chromatography and reverse phase high performance liquid chromatography. When contractile activity on rabbit duodenal muscle was examined, synthetic canine motilin was as active as synthetic porcine motilin. The relative potencies of Lys
1 and Ser
1 derivatives prepared in the same manner as canine motilin were ca. 1/1000 and 1/250, respectively.
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HIDETOSHI TAKAGI, TOHRU HAYAKAWA, TOSHIAKI MIURA, MICHIYA KIMURA
1985 Volume 33 Issue 8 Pages
3317-3323
Published: August 25, 1985
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The mechanism of the color and fluorescence reaction of 17α-hydroxyprogesterone (1) with sulfuric acid was elucidated. When a 97% sulfuric acid solution of 1 was heated at 60°C for 45 min and then diluted two-fold with ethanol, a chromo- and fluorophoric species (λ
max=592nm, λ
em=614nm, abbreviated as χ-592) was produced. From this reaction mixture, 17ξ, 17a-dimethyl-18-nor-D-homoandrosta-4, 6, 8 (14), 13 (17a)-tetraen-3-one (4a) was isolated in 13% yield. Dissolution of the tetraenone (4a) in a 1 : 2 mixture of sulfuric acid and ethanol immediately gave an absorption maximum at 592nm (ε=35200) with fluorescence at 614nm. The proton nuclear magnetic resonance spectrum of 4a in a 1 : 2 mixture of D
2SO
4 and CD
3OD indicated that the chromo- and fluorophoric χ-592 is a hydroxyalkatetraenyl cation (4b), the protonated form of 4a. χ-592 (4b) was shown to be formed from 1 via an intermediary species (λ
max=427nm, λ
em=472nm). The structure of the intermediary species was also assumed to be a steroidal dication (9) having both a hydroxyalkenyl cation in ring A and an alkadienyl cation across rings C and D.
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HARUHISA KIZU, SHINGO KITAYAMA, FUKIO NAKATANI, TSUYOSHI TOMIMORI, TSU ...
1985 Volume 33 Issue 8 Pages
3324-3329
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Twelve saponins, tentatively named HN-saponins A (I), B (II), D
1 (III), D
2 (IV), E (V), F (VI), H (VII), I (VIII), K (X), M (XII), N (XIII) and P (XIV), were isolated from the stem and bark of Hedera nepalensis K. KOCH. (Araliaceae). Compounds II, V, XII, XIII and XIV were identified as Kizuta saponins K
3, K
6, K
10, K
11 and K
12, respectively, which have been isolated from Hedera rhombea BEAN. On the basis of chemical and physicochemical evidence, other saponins were identified as follows : I, a mixture of the β-D-glucopyranosides of campesterol (trace), stigmasterol and β-sitosterol ; III, hederagenin 3-O-β-D-glucopyranoside ; IV, oleanolic acid 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; VI, 3-O-α-L-arabinopyranosyl-hederagenin 28-O-β-D-glucopyranosyl ester ; VII, hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester ; VIII, oleanolic acid 3-O-β-D-glucuronopyranoside ; X, hederagenin 3-O-β-D-glucuronopyranoside. Compounds VI and VII were isolated from nature for the first time, though they had previously been derived from Akebia seed saponin D and Kizuta saponin K
12, respectively, by partial hydrolysis.
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MASASHI TOMODA, NORIKO SHIMIZU, RYOKO GONDA
1985 Volume 33 Issue 8 Pages
3330-3335
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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A representative mucilage, named Okra-mucilage R. was isolated from the roots of Abelmoschus esculentus MOENCH (=Hibiscus esculentus L. ; Okra). The final preparation was homogeneous as determined by ultracentrifugal analysis, cellulose acetate membrane electrophoresis, and gel chromatography. Its water solution gave an intrinsic viscosity value of 33.4. It was mainly composed of partially acetylated acidic polysaccharide, and its molecular weight was estimated to be about 1700000. The polysaccharide was composed of L-rhamnose : D-galactose : D-galacturonic acid : D-glucuronic acid : O-acetyl groups in the molar ratio of 1.1 : 1.9 : 1.0 : 1.0 : 2.0. Methylation and partial acid hydrolysis studies made it possible to deduce the structural features of the polysaccharide in the mucilage.
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FUMIYOSHI ISHIKAWA, HITOSHI YAMAGUCHI, JUNJI SAEGUSA, KAZUE INAMURA, T ...
1985 Volume 33 Issue 8 Pages
3336-3348
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Tetracyclic imidazo [2, 1-b] quinazolinone derivatives (18) with a modified or unmodified alkylene chain were prepared and evaluated for their ability to inhibit platelet aggregation. Most of the compounds were very potent except for some compounds substituted with an amino or a hydroxy group. The structure-activity relationships are discussed.
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KOJI SHIMIZU, SAKAE AMAGAYA, YUKIO OGIHARA
1985 Volume 33 Issue 8 Pages
3349-3355
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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In the course of studies on the metabolism of saikosaponins, which are the main constituents of Bupleurum falcatum L., five new compounds derived from saikosaponins a, c and d were isolated after incubation with acid and snail enzyme. On incubation of saikosaponins a and c at 60°C in a 1 N sulfuric acid-dioxane solution, saikosaponins g and i possessing a homoannular diene moiety at C-9 (11), 12 were isolated, and their structures were elucidated as 3β, 16β, 23, 28-tetrahydroxyoleana-9 (11), 12-diene 3-O-β-D-glucopyranosyl-(1→3)-β-D-fucopyranoside and 3β, 16β, 28-trihydroxyoleana-9 (11), 12-diene 3-O-β-D-glucopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside, respectively. Furthermore, on incubation of saikosaponins b
1, g and b
2 with snail enzyme for 12h at 37°C, prosaikogenins A, H, and D were formed ; they were identified as the 3-β-D-fucopyranosides of saikogenins A, H and D.
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TAICHI OHMOTO, KAZUO KOIKE, TAKESHI HIGUCHI, KEIJI IKEDA
1985 Volume 33 Issue 8 Pages
3356-3360
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Three new β-carboline alkaloids, picrasidines I (I), J (II), and K (III), were isolated from the bark of Picrasma quassioides BENNET. The structures were determined on the basis of spectral analyses and chemical transformations.
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KEIICHI NISHIMURA, TOSHIO MIYASE, AKIRA UENO, TADATAKA NORO, MASANORI ...
1985 Volume 33 Issue 8 Pages
3361-3368
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Eight new guaianolide type glycosides, ixerins M, N, O, P, Q, R, S and T, in addition to 8-epidesacylcynaropicrin-glucoside and macrocliniside A, have been isolated from the methanol extract of lxeris stolonifera A. GRAY (Compositae). The structures of the new compounds were determined on the basis of chemical and spectral data.
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KENJI INAGAKI, SUMIKO YONEHARA, YOSHINORI KIDANI
1985 Volume 33 Issue 8 Pages
3369-3374
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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A derivative spectrophotometric method for the determination of the antitumor agent cis-dichlorodiammineplatinum (II) in urine has been developed. The method is based on the complexation of cis-dichlorodiammineplatinum (II) with N, N'-bis (3-mercapto-2-quinoxalinyl)-1, 3-propanediamine. Optimum conditions for quantification of cis-dichlorodiammineplatinum (II) were established. The complex formed was stable in urine, and the recovery of platinum from urine was 92-95%. Interference arising from urine can be avoided by measurement of the second-order derivative spectrum. The relative standard deviations of the present method were 3.9% and 1.9% for the determination of 0.2 and 2.0 ppm of platinum in urine, respectively.
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HIDEO FUKUDA, TSUYOSHI TANIMOTO, TSUTOMU YAMAHA
1985 Volume 33 Issue 8 Pages
3375-3380
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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The lysozyme assay using 4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside as a substrate was found to show increased sensitivity for lysozyme in the presence of jack bean β-N-acetylhexosaminidase (NAHase). The assay system containing NAHase gave a linear dose-response curve in the range of 10-70μg of lysozyme under conditions of 20-60 min incubation at pH 5.2 and 35°C, and the sensitivity for lysozyme was more than five times higher than that of the fluorometric assay system without the hexosaminidase. The new assay gave values compatible with those of the cell turbidimetric assay using Micrococcus lysodeikticus as a substrate in the estimation of lysozyme in pharmaceutical preparations. The present assay system has better reproducibility than the cell turbidimetric assay and may serve as a substitute for the latter.
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YUTAKA SAITO, MASAKI MIFUNE, KENJI IKEGAMI, KIMIYA OKAZAKI, JUNICHI OD ...
1985 Volume 33 Issue 8 Pages
3381-3384
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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A new indirect spectrophotometric method for the determination of phosphate ion by the use of solid ferric salt of tetraphenylporphine-trisulfonic acid (TPPSFe) was developed. The method is based on the measurement of the absorbance of TPPS liberated from TPPSFe at its Q band (procedure A) or its Soret band (procedure B). Phosphate ion ranging from 10 to 50μg and from 4 to 20μg could be determined based on the absorption coefficients of 8.2×10
3 at 512nm (procedure A) and 2.2×10
5 at 434nm (procedure B). The advantages of this method are its simple procedure and mild conditions. Procedure A was successfully applied to the determination of phosphate ion liberated from glucose-1-phosphate by acid phosphatase.
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YOSHIO SASAKI, TATSUYA TAKAGI, SULAN HSIU, KEIZO NAKAMURA
1985 Volume 33 Issue 8 Pages
3385-3389
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Many unknown Lennard-Jones (12, 6) potential force constants ε/k [K] of acyclic saturated hydrocarbons could be estimated from the linear relationship between known ε/k [K] (determined from the combined viscosity and 2nd virial coefficient data) and S
o298 (g). The dispersion interaction term E
dis. in gas-liquid chromatography (GLC) can be determined by using the mixture rule as the difference of -2 [ε
iiε
jj]
1/2 for the solute-stationary phase and solute-mobile phase pairs. Parameter ε
ii1/2×10
-8 erg
1/2 is linearly related to logγ measured by GLC of acyclic saturated hydrocarbons under apolar conditions. The correlation between logγ and S
o298 (g), as well as that of logγ against E
dis., supports the dependencies of E
dis. and ΔH
o5 (enthalpy of dissolution) on S
o298 (g).
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MASAYOSHI YAMAGUCHI
1985 Volume 33 Issue 8 Pages
3390-3394
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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The mitochondrial uptake of
45Ca
2+ bound to calcium-binding protein newly isolated from rat liver cytosol was investigated. The binding of
45Ca
2+ to calcium-binding protein increased linearly with increasing amount of the protein.
45Ca
2+ bound to the binding protein was taken up by rat liver mitochondria and microsomes in the presence of 3mM adenosine 5'-triphosphate (ATP) in the incubation medium, while the uptake was slight in the absence of ATP. The mitochondrial uptake of
45Ca
2+ bound to the binding protein started within 15s of the start of incubation and was saturated at 5min. The amount of
45Ca
2+ taken up by the mitochondria from
45Ca
2+-binding protein increased linearly with increasing concentration of the protein-bound
45Ca
2+. The mitochondrial uptake of
45Ca
2+ from the binding protein was markedly inhibited by the presence of mitochondrial calcium uptake inhibitors, ruthenium red (10μM), lanthanum chloride (250μM), and oxidized form of nicotinamide adenine dinucleotide (NAD
+ ; 2.5mM). The present results suggest that the cytosolic calcium-binding protein binds calcium ion in rat liver cytosol and the metal is subsequently transported into the organelles. This protein may play a role in the regulation of the cytosolic calcium ion level.
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NAOHITO OHNO, KAZUYOSHI IINO, TAKAHIRO TAKEYAMA, IWAO SUZUKI, KICHIRO ...
1985 Volume 33 Issue 8 Pages
3395-3401
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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The fruit body of Grifola frondosa, an edible mushroom, is used as a food in Japan. However, the matted mycelium of the fruit body is not utilized, In this paper, structural characterization and antitumor activity of the extracts from the matted mycelium of this fungus were examined. Hot water, cold alkali, and hot alkali extracts of the mycelium all contained polysaccharides ; that in the cold alkali extract was composed of glucose, but those in the hot water and hot alkali extracts contained glucose, mannose and/or xylose. Each fraction showed potent antitumor activity against murine solid tumor, Sarcoma-180. The antitumor activities of the alkali extracts were more potent than that of the hot water extract. By means of DEAE-Sephadex chromatography, α-amylase treatment, and SP-Sephadex chromatography, a neutral β-1, 3-glucan was purified from the cold alkali extract. From the results of nuclear magnetic resonance spectroscopy, methylation, periodate oxidation, enzymic degradation, and physicochemical characterizations, the purified antitumor glucan was concluded to be a β-1, 3-glucan branched at C-6 of every third main-chain glucosyl unit. The structure is quite similar to that of the antitumor glucan obtained from the fruit body of this fungus. It is concluded that the matted mycelium of G. frondosa may be useful as a source of antitumor β-1, 3-glucan.
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TOSHIAKI MIURA, TAKETO OGISO
1985 Volume 33 Issue 8 Pages
3402-3407
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Addition of luminol to the xanthine oxidase system caused the production of chemiluminescence (CL). Superoxide dismutase (SOD) and singlet oxygen (
1O
2) scavengers inhibited the CL, whereas catalase and hydroxyl radical (HO) scavengers had no significant effect, suggesting that
1O
2 species derived from O
-2 is responsible for the light emission of luminol. Addition of unsaturated acids to the xanthine oxidase system in the presence of luminol resulted in quenching of CL, and peroxidation of the unsaturated fatty acids was observed. SOD and
1O
2 scavengers also inhibited the peroxidation of arachidonate, indicating that
1O
2 generated in the xanthine oxidase system participates in the peroxidation reaction.
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TOSHIHIRO FUJII, YASUHIRO AKABANE, YUMIKO TATEISHI, MICHIYO FUJII, YOS ...
1985 Volume 33 Issue 8 Pages
3408-3414
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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The interaction of protein-bound polysaccharide (PS-K) with actomyosin from rabbit skeletal muscle was investigated by measuring the changes in adenosine triphosphatase (ATPase) activity, turbidity, and viscosity. At low ionic strengths, PS-K reduced the actin-activated Mg
2+-ATPase activity of myosin to 20% of the original level, whereas it slightly enhanced the myosin ATPase activity without actin. The inhibition of actin-activated ATPase activity was not reversed by increasing actin concentration and, further, the apparent affinity of myosin for actin was not altered by the addition of PS-K. The extent of inhibition depended on the sequence of addition of myosin, actin, and PS-K, i. e., when PS-K was preincubated first with myosin before adding actin, the most marked inhibition was observed. The changes of actomyosin turbidity induced by PS-K were similar to those of ATPase inhibition. PS-K did not affect the polymerization and depolymerization of actin. Therefore, the inhibitory effects seem to be caused by PS-K bound to myosin filaments.
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KAZUMOTO CHIBA, MASAYOSHI YOSHIDA, ATSUSHI ISHIHARA, JUNICHI SUDO, TSU ...
1985 Volume 33 Issue 8 Pages
3415-3421
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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In this study, the effects of two non-steroidal anti-inflammatory drugs, ibuprofen and bucolome, on plasma levels of sulfonamides (sulfamethizole and sulfanilamide) were investigated in rats. The persistence of sulfamethizole in plasma was prolonged by coadministration of ibuprofen, while it was hardly affected (though the plasma level was slightly lowered) by coadministration of bucolome. No alteration was observed in the persistence or plasma level of sulfanilamide on coadministration of ibuprofen or bucolome. In experiments to investigate the renal excretion of sulfonamides, the clearance ratio of sulfamethizole was markedly decreased after ibuprofen infusion, while bucolome had little effect. From these results, it is speculated that prolongation of the persistence of sulfamethizole in plasma by ibuprofen is mainly caused by competitive interaction between sulfamethizole and ibuprofen at the renal secretory level. In protein binding experiments, ibuprofen and bucolome were found to displace sulfamethizole bound to rat plasma protein. The displacing activity of bucolome was much stronger than that of ibuprofen. This activity of bucolome may increase the tissue distribution and glomerular filtration of sulfamethizole, and thus influence the plasma level and net renal handling of sulfamethizole.
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TSUNEO UMEDA, NORIAKI OHNISHI, TERUYOSHI YOKOYAMA, TSUTOMU KURODA, YOS ...
1985 Volume 33 Issue 8 Pages
3422-3428
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Acetazolamide has two polymorphic forms (forms A and B), which were characterized by X-ray powder diffractometry, infrared spectrophotometry, differential scanning calorimetry and thermogravimetry. The solubility and dissolution rate of form B were about 1.1 times higher than those of form A. The transition temperature obtained by solubility measurement was 78°C, and the heats of transition (ΔH
trans) calculated by solubility measurement and by differential scanning calorimetry were 2.6 and 1.7 kJ·mol
-1, respectively. The free energy change (ΔG
25c) between the two polymorphic forms was calculated to be 357 J·mol
-1. In addition, the kinetics of isothermal transition of form A to form B at high temperature was investigated by means of differential scanning calorimetry ; this transition appeared to follow the mechanism of random nucleation with first-order kinetics. The activation energy for this transition was calculated to be 246 kJ·mol
-1 from the Arrhenius plots.
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AKIHIKO HASEGAWA, RIE KAWAMURA, HIROSHI NAKAGAWA, ISAO SUGIMOTO
1985 Volume 33 Issue 8 Pages
3429-3435
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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Enteric coating agents, such as hydroxypropylmethylcellulose phthalate, methacrylic acidmethacrylic acid methyl ester copolymer, cellulose acetate phthalate, carboxymethylethylcellulose, were investigated as possible carriers for poorly water-soluble drugs in solid dispersions. In most cases, the drugs were present in amorphous form in the solid dispersions of 1 : 3 weight ratio of drug to polymer, though griseofulvin and phenytoin were not. Dissolution behavior was investigated using nifedipine, griseofulvin or spironolactone as a drug. The amorphous solid dispersions showed supersaturation phenomena in JPX 2nd fluid (pH 6.8), but the dissolution rate was suppressed in JPX 1st fluid (pH 1.2). It was confirmed that the physicochemical state of solid dispersions plays a predominant role in the dissolution of the drug from the solid dispersions.
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NAGAHIKO YUMITA, RYUICHIRO NISHIGAKI, KOSHIRO UMEMURA, TOSHIHIRO HAYAS ...
1985 Volume 33 Issue 8 Pages
3436-3439
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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The serum concentrations of unchanged and glucuronized drug were determined after intravenous injection of pentazocine (PA) in rabbits. A compartment model isolating the liver from the central compartment was proposed to explain the observed time courses of the concentration, and the resulting convolution equation was M (t)=∫
10D (t-θ) G (θ) dθ, where M (t) and D (t) are the serum concentrations of glucuronized PA and unchanged PA after intravenous injection, respectively. The weight function, G (t), which represents the response for a pulse input of glucuronized PA was estimated to be G (t)=0.00933 (e
-0.00818t-e
-0.223t) (min
-1). The simultaneous intravenous administration of salicylamide (SAM) had no effect on the glucuronization of PA in serum. The serum concentration of glucuronized PA calculated by numerical convolution of G (t) and the published serum concentration of unchanged PA after oral administration represents that of glucuronide produced from the unchanged PA which escaped the first-pass effect. This calculated value was far below the published serum concentration of glucuronized PA after oral administration, and the difference represents the glucuronized PA produced by the first-pass effect. The area under the concentration-versus-time curve of glucuronized PA produced by the first-pass effect was 274 times larger than that of glucuronized PA produced from unchanged PA in the serum. Simultaneous oral administration of SAM only inhibits the first-pass effect.
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TOSHIAKI ANDO, YOSHIO KANAYA, KIKUO ASAHINA
1985 Volume 33 Issue 8 Pages
3440-3446
Published: August 25, 1985
Released on J-STAGE: March 31, 2008
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The changes in the physical characteristics of the tablets containing ethylaminobenzoate during storage under drying conditions at different temperatures below the melting point were investigated. Changes in the crushing strength of the tablets, the disintegration properties of the tablets, the penetrating speed of water into the tablets and the pore diameter in the tablets were apparent even below the melting point. These changes tended to become larger at higher storage temperature. Based on a comparison with the results for stored tablets composed of only one component, it is considered that one of the causes of these changes is sintering. It is suggested that these changes are affected by the excipients in the tablets.
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