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JUNZO HIROSE, MASAHIDE NOJI, YOSHINORI KIDANI
1984 Volume 32 Issue 7 Pages
2481-2485
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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On the basis of magnetic circular dichroic (MCD) spectra, the coordination geometries of various adducts of cobalt (II)-bovine carbonic anhydrase were determined. The 8-quinolinecar-boxylate, acetate and oxalate adducts of cobalt (II)-bovine carbonic anhydrase, which had two clearly separated negative MCD bands at 17500 cm
-1 and 21000-22000 cm
-1, were five-coordinate. The MCD spectra of the Cl
-, Br
-, benzoate, and 3-quinolinecarboxylate adducts of cobalt (II)-bovine carbonic anhydrase were very complex and were interpreted in terms of the overlapping of MCD spectra of tetrahedral and five-coordinate adducts. The coordination geometry of the alkaline form of cobalt (II)-bovine carbonic anhydrase is discussed on the basis of the above results.
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HIDETOSHI TAKAGI, HIDEHARU ODAI, TOSHIAKI MIURA, MICHIYA KIMURA
1984 Volume 32 Issue 7 Pages
2486-2495
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The
1H-and
13C-nuclear magnetic resonance spectra of progesterone (VII) in 97% H
2SO
4 indicated the formation of a dication (VIII), which was transformed to another dication χ-301 (X) consisting of a hydroxyalkenyl cation moiety in ring A and a cyclopentenyl one in ring D, when the acid solution was heated at 80°C for 2h. At a reduced acid-strength of the reaction system, X was converted to the hydroxyalkatrienyl cation χ-482 (XIV) through an acid-base equilibrium on the one hand, and to the hydroxyalkatetraenyl cation χ-600 (XV) by an oxidative process on the other. The structures of these cations were confirmed by isolating the corresponding conjugate bases, 17ζ-isopropyl-18-nor-13ζ-androsta-4, 6, 8 (14)-trien-3-one (XII) and 17-isopropyl-18-norandrosta-4, 6, 8 (14), 13 (17)-tetraen-3-one (XIII), from the colored solutions. The pK
a values of the cations XIV and XV were-4.6 and -3.8, respectively. On the basis of these results, a mechanism is proposed for the title reaction.
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NOBUHARU KATO, YASUMASA HAMADA, TAKAYUKI SHIOIRI
1984 Volume 32 Issue 7 Pages
2496-2502
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The pyrrolidine enamine 1 of deoxybenzoin reacted with diphenyl phosphorazidate (DPPA, (C
6H
5O)
2P (O) N
3) to give two amidines, the 1, 2-migration product 7a and the 1, 3-dipolar elimination product 8a in a ratio of 77 : 23. The reaction of DPPA with the enamine 2 of benzyl 2-pyridyl ketone proceeded slightly better in the presence of boron trifluoride etherate, giving both the 1, 2-migration and 1, 3-dipolar elimination products 7b and 8b. However, the main products in the reaction of DPPA with the pyrrolidine enamine 3 of 2-phenacylpyridine were 4-phenyl-5-(2-pyridyl)-1, 2, 3-triazole (11) and diphenyl N-pyrrolidinophosphoramidate (12e). Some other 1, 3-dipolar cycloadditions of enamines with organic azides were also investigated.
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MASAYUKI ONDA, AKIKO HATANO, HIROKO YAMAGUCHI, NORIKO SATO
1984 Volume 32 Issue 7 Pages
2503-2515
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Proton assignments of the cycloadducts of anhydromethylberberines with dienophiles have been made by reference to the carbon-13 nulcear magnetic resonance spectra. The correlation between the molecular geometries and the proton chemical shifts is discussed on the basis of the variable-temperature nuclear magnetic resonance spectral data.
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MASANORI SAKAMOTO, TAKASHI AKIMOTO, KYOKO FUKUTOMI, KEITARO ISHII
1984 Volume 32 Issue 7 Pages
2516-2521
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The reaction of benzimidazoline-2-thione (2) with diketene (1) gave the oxazine derivative 3 and the thiazine derivative 4. However, the reaction of 2-indolinethione (6) with diketene afforded only the thiazine derivative 7. On the other hand, no cyclized compound was obtained from 2-indolinone (8) and diketene. The reactions of N, N'-diphenylthiourea (11) and 2-aminobenzothiol (14) with diketene were also studied ; 11 and 14 gave the thiouracil 12 and the benzothiazine 16, respectively.
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AKIRA SHIOZAWA, YUHICHIRO ICHIKAWA, CHIKARA KOMURO, SHUJI KURASHIGE, H ...
1984 Volume 32 Issue 7 Pages
2522-2529
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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5-Methyl-(4a), 7-methyl-(4b), and 8-methyl-5, 6, 7, 8-tetrahydro-1, 6-naphthyridine (4c) were synthesized by chemical modification of pyridine derivatives. On the other hand, the synthesis of the compounds (20b, c) having a methyl group in the aromatic ring of 5, 6, 7, 8-tetrahydro-1, 6-naphthyridine was accomplished by the condensation of 1-benzyl-4-piperidinone with the corresponding 3-amino-enones followed by debenzylation. The pathway of the condensation is briefly discussed.
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MASANORI NAGATA, HIROKI TAKAHATA, YOSHIRO HIRAI, KEIICHI AOE, TAKAO YA ...
1984 Volume 32 Issue 7 Pages
2530-2535
Published: July 25, 1984
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6, 7-Dihydro-6-methyl-5-oxo-5H-pyrrolo [3, 4-b] pyridine (1) was heated with 3, 4-methylene-dioxyphenethyl bromide to give the corresponding quaternary bromide (2), which was subjected to catalytic hydrogenation to afford 2, 3-methylenedioxy-16-methyl-17-oxo-8, 16-diaza-9, 10-seco-estra-1, 3, 5 (10)-triene (5). The cyclization of 5 was achieved with mercuric acetate in 5% acetic acid solution, leading to 2, 3-methylenedioxy-16-methyl-17-oxo-8, 16-diaza-estra-1, 3, 5 (10)-triene (7). The structure of 7 was established by X-ray crystallographic analysis.
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SADAO MAEDA, MAMORU SUZUKI, TAMEO IWASAKI, KAZUO MATSUMOTO, YOSHIO IWA ...
1984 Volume 32 Issue 7 Pages
2536-2543
Published: July 25, 1984
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Various 2-mercapto-4-substituted-5-imidazolecarboxylates (5) were synthesized by the reaction of C-acylamino acid methyl esters (4) with potassium thiocyanate. Hydrolysis followed by decarboxylation of the imidazole carboxylates (5) gave 2-mercapto-4-substituted imidazoles (8) in good yields. Furthermore, the imidazoles (8) were also directly obtained by the reaction of aminoketones (9) with potassium thiocyanate. These compounds (8) exhibited antiinflammatory activities against carrageenan-induced rat paw edema. Among the compounds tested, 2-mercapto-4-(3-thienyl) imidazole (8r) showed the best therapeutic index value, giving a value comparable to that of mefenamic acid.
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MIKIO TANIGUCHI, TOMIKO ANJIKI, MASAKO NAKAGAWA, TOHRU HINO
1984 Volume 32 Issue 7 Pages
2544-2554
Published: July 25, 1984
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The 5-hydroxytryptophan derivative 12 was prepared in 60% yield from the tryptophan derivative 8 by selective oxidation of the cyclic tautomer 9 with Fremy's salt or Pb (OAc)
4-CF
3COOH to the p-quinoneimine 10, followed by reduction and ring-opening. By analogous oxidation, serotonin was prepared from tryptamine. On the other hand, the oxidation of the N
a-acetyl-cyclic tautomers (16 and 22) with Pb (OAc)
4-CF
3COOH followed by methylation gave the 5-and 6-methoxy derivatives (17, 18, 23, and 24) in 20-40% yields. These compounds were readily converted to the 5-and 6-methoxytryptophan derivatives (20, 21) by acid treatment. These methods are the first practical hydroxylation procedures to be reported for tryptophans.
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YUTAKA YAMAMOTO, YASUO MORITA
1984 Volume 32 Issue 7 Pages
2555-2559
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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6-Methyl-2-phenyl-4H-1, 3-oxazin-4-one (1) underwent initial attack of the anions of lactams (2), such as ε-capro-(2a), δ-valero-(2b), and γ-butyro-lactams (2c), at the 4-position of the ring to give the corresponding α-substituted lactams (3a-c). Reaction of 1 with N-trimethylsilyl derivatives (6a-c) of 2 in the presence of lithium diisopropylamide afforded the 2, 3-dihydro-4H-1, 3-oxazin-4-one derivatives (7a-c), respectively. Similar treatment of 1 with O-methyl derivatives (9a-c) of 2 yielded the corresponding bicyclic heterocycles (10a-c).
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TETSUHIDE KAMIJO, HIROMU HARADA, KINJI IIZUKA
1984 Volume 32 Issue 7 Pages
2560-2564
Published: July 25, 1984
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Ketoximes undergo the Beckmann rearrangement and primary carboxamides are dehydrated to nitriles on treatment with N, N'-carbonyldiimidazole and an excess of reactive halide. The reaction can be carried out in high yields under neutral reaction conditions by a simple procedure ; quaternization of the imidazole ring with reactive halides effectively promotes the reaction.
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HIROSHI AKIMOTO, AKIYOSHI KAWAI, NAOTO HASHIMOTO, HIROAKI NOMURA
1984 Volume 32 Issue 7 Pages
2565-2570
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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As part of our recent search for new semisynthetic analogs of maytansinoids having a better therapeutic ratio than maytansine, we synthesized 3-epimaytansinoids (VIIIa-c) starting from ansamitocin P-3, a fermentation product of Nocardia sp., via maytansinol (I). A key intermediate, 3-epimaytansinol (VI), was synthesized by oxidation of I with pyridinium chlorochromate to 3-maytansinone (IV), followed by stereoselective reduction with NaBH
4. Esterification of VI with appropriate carboxylic acids gave the corresponding 3-epimaytansinoids (VIIIa-c) in high yields. These compounds did not show the biological activity characteristic of natural maytansinoids to any appreciable degree.
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HIROSHI SHIMIZU, NORIHIRO UEDA, TADASHI KATAOKA, MIKIO HORI
1984 Volume 32 Issue 7 Pages
2571-2590
Published: July 25, 1984
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The stereochemistry of novel ring expansions of benzothiazoline sulfoxides to benzothiazines by reaction with acetic anhydride was examined. Reaction of trans-3-acetyl-2-ethyl-2-methyl-benzothiazoline 1-oxide with acetic anhydride afforded 4-acetyl-3-ethylidene-2, 3-dihydro-4H-1, 4-benzothiazine and 4-acetyl-3-ethyl-4H-1, 4-benzothiazine, which are the products expanded in the direction of the substituent cis to the sulfoxide moiety, and 4-acetyl-2-methyl-3-methylene-2, 3-dihydro-4H-1, 4-benzothiazine and 4-acetyl-2, 3-dimethyl-4H-1, 4-benzothiazine, which are the products expanded in the opposite direction (trans). Similar results were also obtained from the reaction of the sulfoxides, trans-4-acetyl-2-benzyl-2-methylbenzothiazoline 1-oxide, and cis-and trans-3-acetyl-2-ethoxycarbonylmethyl-2-methylbenzothiazoline 1-oxides, with acetic anhydride. Thus, it was confirmed that this ring expansion is non-stereospecific and quite different from the similar ring transformation of penicillin sulfoxides to cephalosporins. The major factor in this non-stereospecificity was found to be an easy cleavage of the C
2-S bond of the benzothiazoline ring due to electronic effects of the nitrogen atom at the β-position to the sulfur atom in comparison with the ring expansions of related six-membered benzothiazine sulfoxides and thiochroman sulfoxides.
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KOSAKU HIROTA, YUKIO KITADE, FUMIAKI IWAMI, SHIGEO SENDA
1984 Volume 32 Issue 7 Pages
2591-2595
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Treatment of O
2, 2'-anhydrouridine (1) with phosphorus oxychloride in dimethylformamide (DMF) at 60°C afforded both 2', 5'-dichloro-2', 5'-dideoxyuridine (2a) and 2', 5'-dichloro-2', 5'-dideoxy-3'-O-formyluridine (3a). The reaction of 1 with phosphorus oxybromide in DMF gave the corresponding 2', 5'-dibromo derivatives (2b) and (3b). O
2, 5'-Anhydro-2', 3'-O-isopropylideneuridine (4) was treated with the Vilsmeier reagent (DMF/POX
3) to give the corresponding 5'-halogeno-5'-deoxy-2', 3'-O-isopropylideneuridines (5a and 5b) in high yields. Under the same conditions, the reaction of 6, 5'-cyclo-2', 3'-O-isopropylideneuridine (6) with the Vilsmeier reagent (DMF/POX
3) afforded the corresponding 1-(5-halogeno-5-deoxy-2, 3-O-isopropylidene-β-D-ribofuranosyl)-5-dimethylaminomethylenebarbituric acids (7a and 7b) in high yields.
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HISASHI MATSUNAGA, MIKI SONODA, YUKIHIKO TOMIOKA, MOTOYOSHI YAMAZAKI
1984 Volume 32 Issue 7 Pages
2596-2601
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The reactions of 2-amino-3-cyano-1-ethoxycarbonyl-4, 5-dihydropyrrole (Ia) and 2-amino-3-cyano-1-ethoxycarbonyl-5-methyl (or 4-phenyl)-4, 5-dihydropyrrole (Ib or Ic) with dimethyl acetylenedicarboxylate and methyl propiolate gave the corresponding 7-amino-4-cyano-1-ethoxycarbonyl-2, 3-dihydro-1H-azepines (IIa-c and IIIa-c). On heating with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone, IIc and IIIc were converted into dimethyl 6-amino-3-cyano-5-ethoxycarbonylamino-4-phenyl-1, 2-benzenedicarboxylate (V) and methyl 6-amino-3-cyano-5-ethoxycarbonylamino-4-phenylbenzenecarboxylate (VI), respectively.
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MASAYUKI SATO, HIROMICHI OGASAWARA, TETSUZO KATO
1984 Volume 32 Issue 7 Pages
2602-2608
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The ring transformation of 2, 2-dimethyl-1, 3-dioxin-4-ones (1) to nitrogen heterocycles was studied. Heating of 1 with imines such as Schiff bases gave rise to [2+4] cycloadducts of imines to acylketenes (2), i.e., 3, 4-dihydro-1, 3-oxazin-4-one derivatives (4). Similarly, 1 reacted with carbodiimides to yield 2-imino-1, 3-oxazin-4-one derivatives (11 and 12). The reaction of 1 with phenyl isocyanate gave 3-phenyl-1, 3-oxazine-2, 4-diones (15), while the reaction with 2-pyridyl isocyanate gave pyrido [1, 2-a] pyrimidin-4-one derivatives (18).
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SHIGEKO OZAKI, SUSUMU NISHIGUCHI, MASAICHIRO MASUI
1984 Volume 32 Issue 7 Pages
2609-2616
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Anodic oxidation of N-alkylhydroxylamines with and without a β-hydroxy group was studied by cyclic voltammetry and controlled potential electrolysis in aqueous buffer solution of pH 8.8. The hydroxylamines with a β-hydroxy group were oxidized initially to the corresponding nitroxides and gave the final products via two routes ; i) cleavage of the (α) C-(β) C bond to give aldehydes and oximes, and ii) disproportionation of the nitroxides to form the nitroso compounds. The hydroxylamines without a β-hydroxy group did not undergo cleavage of the (α) C-(β) C bond and gave nitroso compounds. Substituents on the α and β carbons affected the product distribution. When a phenyl group or two methyl groups were present on the (β) C, or one methyl group was present on both (α) C and (β) C, (α) C-(β) C bond cleavage was predominant.
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TAKAO KONOSHIMA, TOKUNOSUKE SAWADA
1984 Volume 32 Issue 7 Pages
2617-2621
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Two monoterpene glycosides 1 and 2 were isolated from the fruits of Gymnocladus chinensis BAILLON (Leguminosae). On the basis of chemical and physicochemical evidence, these glycosides were characterized as (6S)-2-trans-6-α-L-arabinopyranosyloxy-2, 6-dimethyl-2, 7-octadienoic acid and (6S)-2-trans-2, 6-dimethyl-6-[3-O-(β-D-glucopyranosyl)-4-O-(2-methylbutyroyl)-α-L-arabino-pyranosyloxy]-2, 7-octadienoic acid.
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MASAO FUJITA, MIKIKO YAMADA, SHOICHI NAKAJIMA, KENICHI KAWAI, MASAHIRO ...
1984 Volume 32 Issue 7 Pages
2622-2627
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The O-methylation effect on the carbon-13 nuclear magnetic resonance chemical shifts of ortho-disubstituted phenols was investigated. In phenols with nonconjugated ortho-disubstituents (1-10), O-methylation caused a downfield shift by an average of 5.2 ppm for the ortho-carbons (C-2 and -6), and a downfield shift by an average of 4.6 ppm for the para-carbon (C-4). These shift values are significantly different from those observed in ortho-monosubstituted and ortho-nonsubstituted phenols. This regularity is very useful for the spectral interpretation of some natural products with an ortho-disubstituted phenol group and for the determination of the position of the methoxy group in such compounds. Two new phthalides, silvaticol (15) and O-methylsilvaticol (16), were isolated along with nidulol (17) from Aspergillus silvaticus. In the course of the structure determination of these compounds, the O-methylation effects of ortho-mono-and ortho-disubstituted phenols were successfully applied to these phthalides. The structures of silvaticol and O-methylsilvaticol were determined as 6-hydroxy-4-methoxy-5-methylphthalide and 4, 6-dimethoxy-5-methylphthalide, respectively.
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KUNIO HIROI, RYUICHI KITAYAMA, SHUKO SATO
1984 Volume 32 Issue 7 Pages
2628-2638
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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A highly efficient and general synthetic route to optically active sulfinates by the stereospecific boron trifluoride etherate-catalyzed esterification of sulfinamides was developed. Dramatic solvent effects were observed in the thermal transformation of allyl sulfinate derivatives to sulfones. Heating of chiral trans-and cis-allyl sulfinates, (S)-(-)-3a, c, e and (S)-(-)-3b, d, f, in N, N-dimethylformamide at 90-120°C provided chiral sulfones (S)-(+)-and (R)-(-)-5, 6, 7 in good yields, respectively, with exceedingly high stereospecificity.
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KATSUHIDE MATOBA, NORIO KARIBE, TAKAO YAMAZAKI
1984 Volume 32 Issue 7 Pages
2639-2645
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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2-Methoxy-4, 4-dimethyl-2-cyclohexenone (II) afforded 5, 6-epoxy-6-methoxy-4, 4-dimethyl-6-hexanolide (III) upon reaction with m-chloroperbenzoic acid in 1, 1, 1-trichloroethane. On the other hand, the treatment of II with the same reagent in an aqueous disodium orthophosphate-methylene chloride system at 4°C gave 2, 3-epoxy-2-methoxy-4, 4-dimethylcyclohexanone (V), which could be converted to methyl 2-hydroxy-1-methoxy-3, 3-dimethylcyclopentanecarboxylate (VI). 2-Methoxy-4, 4-dimethyl-2, 5-cyclohexadienone (I) afforded 5, 6-epoxy-2-methoxy-4, 4-dimethyl-2-cyclohexenone (VIII) upon reaction with hydrogen peroxide in a basic medium. The reaction of I with m-chloroperbenzoic acid at room temperature gave 5, 6-epoxy-6-methoxy-4, 4-dimethyl-2-cyclohexenone (X). Neither VIII nor X gave the expected 2, 3, 5, 6-diepoxy-2-methoxy-4, 4-dimethylcyclohexanone (VII), but afforded 2, 3, 5, 6-diepoxy-6-methoxy-4, 4-dimethyl-6-hexanolide (IX).
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SHOJI KISHIMOTO, MICHIYUKI SENDAI, MITSUMI TOMIMOTO, SHOHEI HASHIGUCHI ...
1984 Volume 32 Issue 7 Pages
2646-2659
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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In the course of the chemical modification of sulfazecin, 3-[2-(2-aminothiazol-4-yl)-(Z)-2-(substituted oxyimino) acetamido]-4-methoxycarbonyl-2-azetidinone-1-sulfonic acids were synthesized starting from cis-1-(2, 4-dimethoxybenzyl)-4-methoxycarbonyl-3-phthalimido-2-azetidinone (2). These new 4-substituted derivatives showed more potent antimicrobial activities against gram-negative bacteria than did the corresponding 4-unsubstituted compounds, and the derivatives having 3, 4-cis stereochemistry were more active than the trans isomers, especially against P. aeruginosa and some β-lactamase-producing bacteria. The reported procedure for the cycloaddition reaction used to prepare 2 was investigated in detail ; by the use of a 20% excess of triethylamine, 2 was easily obtained in the yield of 72% as colorless crystals. A possible intermediate of β-lactam formation in this cycloaddition reaction, an acyl iminium salt (6), was isolated as crystals and converted into β-lactams by treatment with 1, 8-diazabicyclo [5. 4. 0]-7-undecene.
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NOBUTAKA FUJII, SHIROH FUTAKI, KOICHI YASUMURA, HARUAKI YAJIMA
1984 Volume 32 Issue 7 Pages
2660-2665
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The mesitylenesulfonyl (Mts) group was introduced at the N
in of tryptophan by Illi's method. This group is stable under various conditions required for practical peptide synthesis, such as treatments with dil. alkali, hydrazine hydrate, TFA and even 4 N HCl-dioxane or 25% HBr-AcOH. HF is not able to remove this protecting group, but it can be smoothly cleaved by 1 M trifluoromethanesulfonic acid/TFA or methanesulfonic acid. The usefulness of this new tryptophan derivative, Trp (Mts), for practical peptide synthesis was demonstrated by the synthesis of cholecystokinin-heptapeptide as an example.
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TADASHI KATAOKA, KIMINORI TOMIMATSU, HIROSHI SHIMIZU, MIKIO HORI
1984 Volume 32 Issue 7 Pages
2666-2675
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Selenoxanthene 10-oxides (5a-d) reacted with methyl propiolate, dimethyl and diethyl acetylenedicarboxylates to afford selenoxanthen-10-io [formyl (or alkoxalyl) alkoxycarbonyl]-methanides (6a-i). The 9-isopropyl derivative gave only trans-ylides and the 9-phenyl congener formed cis-and trans-ylides. The stereochemistry is discussed on the basis of the nuclear magnetic resonance spectral data. Reduction of the selenoxanthenium ylides with sodium borohydride afforded the ylide lactones (16a-c) and the ylide alcohols (17a-f). The product ratio depended on the solvent used.
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TAKASHI TANAKA, TOKIKO SUEYASU, GENICHIRO NONAKA, ITSUO NISHIOKA
1984 Volume 32 Issue 7 Pages
2676-2686
Published: July 25, 1984
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Six new galloyl and p-hydroxybenzoyl esters (2-7) of benzophenone C-glucosides have been isolated, together with a new benzophenone C-glucoside (1), from the leaves of Mangifera indica L. (Anacardiaceae). On the basis of chemical and spectroscopic evidence, the structures of these compounds have been established as maclurin 3-C-β-D-glucoside (1), maclurin 3-C-(6"-O-p-hydroxybenzoyl)-β-D-glucoside (2), maclurin 3-C-(2"-O-galloyl-6"-O-p-hydroxybenzoyl)-β-D-glucoside (3), maclurin 3-C-(2"-O-p-hydroxybenzoyl-6"-O-galloyl)-β-D-glucoside (4), maclurin 3-C-(2", 3", 6"-tri-O-galloyl)-β-D-glucoside (5), iriflophenone 3-C-(2", 6"-di-O-galloyl)-β-D-glucoside (6) and iriflophenone 3-C-(2", 3", 6"-tri-O-galloyl)-β-D-glucoside (7). (-)-Epicatechin 3-O-gallate (9), mangiferin (10), isomangiferin (11) and a new xanthone C-glucoside gallate, mangiferin 6'-O-gallate (8), have also been isolated and their structures have been similarly characterized. Furthermore, the above plant source contained polygalloylglucoses which were characterized on the basis of chemical and high performance liquid chromatographic analyses as a mixture of penta-to undecagalloylglucoses based on a 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose core. Maclurin 3-C-glucoside (1) has been transformed enzymatically to mangiferin (10) and isomangiferin (11), and it has become clear that 1 is a key intermediate in the biosynthesis of 10 and 11.
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YOSHIMITSU NAGAO, KAORU SENO, KOHJI KAWABATA, TADAYO MIYASAKA, SACHIKO ...
1984 Volume 32 Issue 7 Pages
2687-2699
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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A functional heterocycle, 3-acyl-1, 3-thiazolidine-2-thione [ATT (1)] has been shown to be effective as an acylating reagent for the amino group. ATT (1) was readily prepared by several methods, and reacted with various amino compounds in CHCl
3, CH
2Cl
2, THF, EtOH, THF-H
2O, or sulfolane to afford the corresponding amides, 2a-w and 3-10 in very high yields within a short time. This reagent exhibits high chemo-selectivity. Its reaction with the diamines 13 and 15 and the triamine 29, which include a primary amino group (s) and a secondary amino group, gave the products acylated only at the primary amino group (s), 14, 16, and 30, respectively, in high yields. Aminoalcohols and aminophenols were chemoselectively converted into acylaminoalcohols and acylaminophenols, respectively, by ATT (1). By utilizing this method, several amide alkaloids (26, 28, 30, and 34) were efficiently synthesized. This new aminolysis can be monitored by the disappearance of the yellow color of the starting materials, ATT (1) ; it is remarkably characteristic of this reaction.
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SUSUMU TSUSHIMA, YOSHIO YOSHIOKA, SEIICHI TANIDA, HIROAKI NOMURA, SHOS ...
1984 Volume 32 Issue 7 Pages
2700-2713
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Various carbamate analogs of lysophospholipids, N-alkyl-and alkenylcarbamoyl phospholipids (ACPLs), were synthesized and their antimicrobial properties were examined. The ACPLs studied differed in certain aspects of their chemical structure : the polar-head base, the aliphatic nonpolar tail attached to the carbamate nitrogen and the molecular backbone, e.g., 2-O-methylglycerol and 1, 3-propanediol. In contrast to lysolecithin and lecithin, the majority of the ACPLs showed inhibitory activities against Tetrahymena pyriformis (protozoan) and a range of fungi. In the series of ACPLs studied, the maximal inhibitory activities were observed with 2-O-methyl-1-O-(N-tetradecyl) carbamoylglycero-3-phosphocholine (3-C
14-A) and its 2-demethoxy compound (4-C
14-A). In comparison with clotrimazole, these compounds showed more potent activities against T. pyriformis, and comparable or lower activities against human pathogenic and phytopathogenic fungi. The relationships between structure and antimicrobial activity are discussed.
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HIROSHI TAKAHASHI, YASUHIRO CHIDA, TSUTOMU SUZUKI, HIRAKU ONISHI, SAIZ ...
1984 Volume 32 Issue 7 Pages
2714-2723
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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New optically pure (1S, 1'S)-and (1R, 1'R)-1-cycloalkyl-N-2'-hydroxy-1'-isopropylethyl-2-phenylethylamine hydrochlorides (3a-j) were synthesized in good yields. The analgesic activities of these hydrochlorides were evaluated by the acetic acid writhing method and the bradykinin-induced flexor reflex method. The structure of 3f'·HCl was elucidated by X-ray analysis. The relationship between the analgesic activity and the conformation of the 1-2 bond of these amines is discussed.
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MICHINORI KUBO, HIDEAKI MATSUDA, MOTOHARU TANAKA, YOSHIYUKI KIMURA, HI ...
1984 Volume 32 Issue 7 Pages
2724-2729
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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A 70% methanol extract of Scutellariae Radix, the dried root of Scutellaria baicalensis GEORGI, and its main flavonoid components, baicalin, baicalein and wogonin, have been screened in comparison with three standard anti-inflammatory agents, phenylbutazone, indomethacin and dexamethasone, for activity in various experimental models of inflammation. All of the test substances were found to inhibit an increase in vascular permeability in mice induced by acetic acid and to reduce acute paw edema in rats induced by compound 48/80. They also suppressed the secondary lesion in developing adjuvant-induced arthritis in rats. Since these substances from Scutellariae Radix were found to be effective in both the acute and chronic phases of inflammation, the crude drug Scutellariae Radix can be considered as having anti-inflammatory activity.
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HIROKI TSUKAMOTO, SUEO HISADA, SANSEI NISHIBE
1984 Volume 32 Issue 7 Pages
2730-2735
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Four new lignans, (+)-1-acetoxypinoresinol [(1S, 2R, 5R, 6S)-1-acetoxy-2, 6-bis (4-hydroxy-3-methoxyphenyl)-3, 7-dioxabicyclo [3. 3. 0] octane] (1), (+)-1-hydroxypinoresinol (2), (+)-1-acetoxypinoresinol 4"-O-methyl ether (3) and (+)-1-hydroxypinoresinol 4"-O-methyl ether (4), and two known lignans, (-)-olivil (5) and (+)-cyclo-olivil (6), were isolated from the bark of Olea europaea L. (Oleaceae). Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. The lignans 1, 2 and 3 were also isolated from the bark of Olea africana MILL. (Olea europaea L. subsp. africana (MILL.) GREEN), and lignans 5 and 6 from the bark of Olea capensis L.
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TAKAYASU KITAGAWA, KUMIKO IWAKURA, MASAKO OHSUGI, EIZO HIRAI
1984 Volume 32 Issue 7 Pages
2736-2744
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Isouron (1) and its isomer, 1-(3-tert-butylisoxazol-5-yl)-3, 3-dimethylurea (2), were determined by a colorimetric method with p-dimethylaminocinnamaldehyde (DACA) as the reagent. Compounds 1 and 2 were hydrolyzed to give 3-amino-5-tert-butylisoxazole (3) and 5-amino-3-tert-butylisoxazole (4), respectively, which were transformed into colored substances by reaction with DACA. The former colored product was a Schiff base but the latter product had a different absorption maximum from the corresponding Schiff base. The latter color reaction resulted in a bathochromic shift as compared with Schiff base formation at the 5-position. Traces of 2 (more than 0.05%) in 1 could be estimated precisely together with the quantitation of 1 by making use of this bathochromic effect.
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KAZUHIRO WATANABE, REIJI KIMURA, ITSUO YOSHIZAWA
1984 Volume 32 Issue 7 Pages
2745-2751
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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When estradiol 17-sulfate was incubated with rat liver microsomes in the presence of a reduced nicotinamide adenine dinucleotide phosphate (NADPH)-generating system, 4-hydroxyestradiol 17-sulfate was obtained as a minor product accompanying the major metabolite, 2-hydroxyestradiol 17-sulfate. This 4-hydroxylation was shown to occur without cleavage of the conjugate group. At the substrate concentration of 200 μM, which is about twice the K
m value of estradiol 17-sulfate 2-hydroxylase, the amounts of 2-and 4-hydroxylated products formed by liver microsomes from male rats were 15.03±1.43 and 0.23±0.01%, respectively. Analogous results were obtained with microsomes from female rats under the same conditions : the yields of 2-and 4-hydroxylated metabolites were 8.75±0.97 and 0.14±0.02%, respectively. Thus, the relative ratios of 2-and 4-hydroxylation of estradiol 17-sulfate were approximately 60 : 1 in both sexes. A synthesis of the authentic conjugate, 4-hydroxyestradiol 17-sulfate, and a method for its assay by high-performance liquid chromatography with an electrochemical detector are also described.
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JUN HAGINAKA, HIROYUKI YASUDA, TOYOZO UNO, TERUMICHI NAKAGAWA
1984 Volume 32 Issue 7 Pages
2752-2758
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Although sulbactam has no ultraviolet (UV) absorption maximum above 200 nm, it was found to be easily degraded in alkaline methanol and in alkaline aqueous solution to yield products having UV absorption maxima at 267 nm and 278 nm, respectively. An ion-pair reversed-phase high-performance liquid chromatographic (HPLC) method utilizing this alkaline degradation as a postcolumn reaction has been developed for the determination of sulbactam in plasma and urine. A high and reproducible detector response due to the degradation product (s) was obtained when methanol was used as an organic modifier of the eluent. The HPLC and postcolumn reaction conditions were as follows : column, Develosil ODS-10 (25 cm×4.6 mm i.d.) ; eluent, 5mM tetra-n-butylammonium bromide+1mM Na
2HPO
4+1mM NaH
2PO
4 solution/methanol=3/1 (v/v) for urine samples and 2/1 (v/v) for plasma samples ; flow rate, 1.2 ml/min ; postcolumn reagent, 0.5 N aqueous NaOH solution at a flow rate of 0.6ml/min ; reaction coil, 2m×0.25mm i.d.; detection, 276nm. The procedure was quantitative over a wide range of sulbactam concentrations in plasma and urine down to 0.2 μg/ml and 1.0 μg/ml, respectively. The intra-and inter-assay precisions for plasma at a sulbactam level of 0.53 μg/ml were of the order of 2.0% and 3.5%, respectively.
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YOSHIHISA IWAMOTO, ICHIJI MIFUCHI
1984 Volume 32 Issue 7 Pages
2759-2765
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Treatment of yeast cells with acriflavine followed by illumination with fluorescent lamps resulted in extensive "petite" induction in addition to rapid cell inactivation and nuclear gene mutation. There was no petite induction or cell inactivation in the un-illuminated cells. Such photobiological damage induced by acriflavine was not observed under deoxygenated conditions, such as in the presence of NaN
3, which is a scavenger of singlet oxygen (
1O
2). Photodynamic treatment of yeast cells did not cause marked changes in the CsCl sedimentation profile of mitochondrial DNA. These results showed that the petite induction and the cell inactivation after acriflavine treatment are mainly due to type II photodynamic action.
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TAKAKO YOKOZAWA, TAEKO KOBAYASHI, HIKOKICHI OURA, YUJI KAWASHIMA
1984 Volume 32 Issue 7 Pages
2766-2772
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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In order to clarify the mechanism of action of ginsenoside-Rb
2 in rats, time course experiments were carried out. The maximum decrease in the hepatic glycogen content was found 8h after the treatment, but the content had nearly recovered to the control level 24h after the treatment. In contrast, the level of hepatic glucose-6-phosphate increased, reaching the maximum at 8h. There was also a dramatic increase in the phosphofructokinase activity, peaking at 12h. In addition, accumulation of lipid in adipose tissue was observed 10-12h after the administration of ginsenoside-Rb
2, whereas no significant changes in the total lipid, triglyceride, total cholesterol, phospholipid, glucose, pyruvate, and lactate levels of the liver were observed throughout the experimental period. An increase of hepatic glucose-6-phosphate dehydrogenase activity was observed 2-4h after the treatment, but this response was transitory.
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MINORU KURODA
1984 Volume 32 Issue 7 Pages
2773-2780
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The steady flow behavior, dynamic characteristics and particle size (microscopical counting) of a semisolid O/W cream prepared with cetomacrogol and cetostearyl alcohol were studied. The continuous shear flow curve of this cream was in the form of an anti-clockwise hysteresis loop. Vertical vibration imposed on the cream, using a Sanki viscoelasto recorder, caused a first-order breakdown of viscoelastic structure formed in the cream at a rate of 10
-5 s
-1 for dynamic viscosity and 10
-4 s
-1 for dynamic modulus, while the vibration caused coalescence of the oil globules dispersed in the cream at a rate of 10
-15 s
-1. The destruction of viscoelastic structure was much more rapid than the coalescence.
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JUNJI HIRATE, JUN WATANABE, SHOJI OZEKI
1984 Volume 32 Issue 7 Pages
2781-2787
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The effect of convulsions on teh dispositions of creatinine and urea, which are considered to pass through the water-filled pores of biological membranes easily, was examined by means of plasma analysis and whole-body autoradiography following intravenous administration of each compound to rats during tonic convulsions induced by pentylenetetrazole or electricity. The data on the plasma levels showed that, in convulsed rats, the transfer of creatinine and urea from plasma to tissues was suppressed and the total body clearance of both chemicals was significantly decreased. The results of whole-body autoradiography, which showed decreased or almost stopped blood flow in the intestinal tract, skin, and kidney of convulsed rats, were in good agreement with the above observations.
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YOSHIHISA WATANABE, TAMOTSU KONDO, MASAKI MIYAMOTO, SHIGERU SASAKAWA
1984 Volume 32 Issue 7 Pages
2788-2794
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Two types of microcapsules with different negative surface potentials, poly (1, 4-piperazinediylterephthaloyl) microcapsules containing various concentrations of sodium polystyrene sulfonate solution and hemolysate-loaded polyamide microcapsules of different degrees of carboxylation, were prepared by using an interfacial polymerization technique, and the interactions of these microcapsules with human polymorphonulcear leucocytes (PMNs) were investigated as a function of the surface potential of the microcapsules in the absence and presence of plasma proteins. The rate of oxygen consumption by PMNs was taken as a measure of the interaction. In the absence of plasma proteins, the rate of oxygen consumption by PMNs increased with increasing difference in surface potential between the microcapsules and PMNs. The presence of plasma proteins affected the rate of oxygen consumption, which was dependent on the protein species present and related to the surface potential of the microcapsules. This was interpreted as showing that the surface potential of the microcapsules exerts a great influence on the mode and amount of protein adsorption on the microcapsule surface.
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TSUYOSHI KOJIMA, MASAHIRO NAKANO, KAZUHIKO JUNI, SHOHEI INOUE, YASUHIK ...
1984 Volume 32 Issue 7 Pages
2795-2802
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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To achieve sustained release of local anesthetics from injectable formulations, polycarbonate microspheres were prepared by a solvent-evaporation process. Release patterns of benzocaine, lidocaine, and dibucaine from polycarbonate microspheres in vitro were investigated. Drug contents and sizes of microspheres affected the release patterns of the local anesthetics. The release rate of drugs from smaller microspheres was greater than that from larger microspheres, and with increase in the drug contents, the release rate increased. Microspheres before and after release studies were observed by scanning electron microscopy. It was confirmed that the use of polycarbonate microspheres resulted in sustained release of local anesthetics.
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JUNZO SUZUKI, NAOMI YAGI, SHIZUO SUZUKI
1984 Volume 32 Issue 7 Pages
2803-2808
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Photochemical reaction of phenol with nitrite ion was investigated by ultraviolet irradiation in aqueous solution. The main product of the photochemical reaction was isolated and identified as p-nitrosophenol on the basis of spectral data and high performance liquid chromatography analysis. The production of p-nitrosophenol increased with increases in nitrite ion concentration and irradiation time. The production rate of p-nitrosophenol was enhanced under basic condition or under a nitrogen atmosphere, and was suppressed by the addition of sodium thiocyanate or under an oxygen atmospheres. These results suggested that the photo-nitrosation was caused by NO and OH radicals produced by the photolysis of nitrite ion.
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FUJIO MURAI, MOTOKO TAGAWA, SOREN DAMTOFT, SOREN ROSENDAL JENSEN, BENT ...
1984 Volume 32 Issue 7 Pages
2809-2814
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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On the basis of exhaustive
1H-and
13C-nuclear magnetic resonance (NMR) spectral studies and chemical transformations, the structure of an iridoid glucoside formerly designated as 5-epideoxyloganic acid, isolated from Nepeta cataria L., has been revised to (1R, 5R, 8S, 9S)-deoxyloganic acid, which is renamed 1, 5, 9-epideoxyloganic acid. The absolute configuration of this glucoside was established by its chemical conversion to an antipode of boschnialactone.
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ATSUSHI NUMATA, KAZUKO HOKIMOTO, TSURUKO TAKEMURA, TAKAKO KATSUNO, KYO ...
1984 Volume 32 Issue 7 Pages
2815-2820
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Three compounds having antifeeding activities for the larvae of the yellow butterfly, Eurema hecabe mandarina DE L'ORZA, were isolated from Osmunda japonica THUNB. These compounds were identified as (4R, 5S)-osmundalactone (II), (4R, 5S)-5-hydroxy-2-hexen-4-olide (III) and succinic acid (V), of which the former is the main antifeedant in this plant. (4R, 5S)-5-Hydroxyhexan-4-olide (I) and (3S, 5S)-3-hydroxyhexan-5-olide (IV) were isolated in addition to the antifeedants, and various sterols, fatty alcohols and fatty acid esters were obtained as a mixture. This is the first report of the occurrence of I, II and III as natural products, though they have been artificially prepared.
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YASUNOBU AKIYAMA, JUNKO ABE, TOKUKO TAKANO, TOMOMI KAWASAKI, MASANORI ...
1984 Volume 32 Issue 7 Pages
2821-2824
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The reactions of 3-benzoylacrylonitrile (1a) with 3-amino-5, 5-dimethyl-2-cyclohexenone (2) and ethyl 3-aminocrotonate (4) gave the corresponding pyridine derivatives, 3 and 5, respectively. 3-Ethoxycarbonylacrylonitrile (1b) also reacted with ethyl 3-benzylaminocrotonate (6) and 1-ethoxycarbonylmethylene-1, 2, 3, 4-tetrahydroisoquinoline (9) to give the pyrrolin-5-one derivatives, 7 and 10, respectively.
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CHUNGGI SHIN, YASUCHIKA YONEZAWA, TOYOFUMI YAMADA
1984 Volume 32 Issue 7 Pages
2825-2831
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The synthesis of dehydrotripeptides, composed of an α-amino acid and two α-dehydroamino acid (DHA) residues, by the direct coupling of N-protected △
1-dehydrodipeptide with DHA ester and by the β-elimination of △
1-dehydrotripeptide containing a threonine residue is described. Moreover, the configurational determination of all the new products is discussed.
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ISAO MATSUNAGA, SHIGETOSHI NAGATAKI, ZENZO TAMURA
1984 Volume 32 Issue 7 Pages
2832-2835
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Fluorescein monoglucuronide (III), the main metabolite of fluorescein (I), was chemically synthesized by means of the Koenigs-Knorr reaction. Nuclear magnetic resonance (NMR) spectra and mass spectra (MS) showed that the synthesized material was monoglucuronidated fluorescein. The changes in absorption spectra with pH indicated that this material was an "ether" glucuronide. The glucuronoside linkage was concluded to be β, since this material was hydrolyzed by β-glucuronidase. Thus, the synthesized material was confirmed to be fluorescein mono-β-D-glucuronide.
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JINSAKU SAKAKIBARA, TOYO KAIYA, YOICHI IITAKA
1984 Volume 32 Issue 7 Pages
2836-2840
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Acidic treatment of a grayanol derivative (3), easily formed from grayanotoxin-II (1), afforded a novel cyclization product (7), whose structure was elucidated as 3 (S), 20 : 5 (R), 10 (R)-diepoxy-14 (R), 16 (R)-dihydroxy-1-epi-leucothane by direct X-ray crystallographic analysis.
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TAKAYASU KITAGAWA, MASAKO OHSUGI, EIZO HIRAI
1984 Volume 32 Issue 7 Pages
2841-2844
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Some isoxazole herbicides were determined by a colorimetric method with p-dimethyl-aminocinnamaldehyde (DACA) as the reagent. The compounds (2, 3 and 4) having various substituents at the 3-position were hydrolyzed to 3-amino-5-tert-butylisoxazole (5). The assay method was based on the coloration of 5 with DACA, which was reported previously. The optimum hydrolysis conditions were determined. Compound 5 was obtained from 2, 3 and 4 with sufficient recoveries under neutral, alkaline and acidic conditions, respectively. The raw materials could thus be evaluated effectively by simple assay methods.
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MASASHI TOMODA, NORIKO SHIMIZU, KEIKO KATOH
1984 Volume 32 Issue 7 Pages
2845-2847
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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Procedures for the identification of decoction of Alismatis Rhizoma (rhizome of Alisma orientale JUZEPCZUK or related species) by cellulose acetate membrane electrophoresis, paper partition chromatography, and thin-layer chromatography were developed. These methods are due to the presence of a characteristic new component.
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JUNJI HIRATE, JUN WATANABE, SHOJI OZEKI
1984 Volume 32 Issue 7 Pages
2848-2850
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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The plasma levels of creatinine following intravenous administration to chronically (4 months) CCl
4-treated rats, which have been extensively used as an experimental model of cirrhosis, were compared with those of control rats. The total body clearance of creatinine in chronically CCl
4-treated rats (6.95 ml/min/kg) was about 70% of the control value (9.85 ml/min/kg). This result suggested that the kidney as well as the liver is impaired by CCl
4 treatment. This means that the renal clearance of drugs whose elimination is mainly dependent on the kidney might be decreased by CCl
4 treatment.
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YOSHIKUNI TANIOKA, YUKIO YASUDA, NOBUO AOYAGI, HIROYASU OGATA, NAHOKO ...
1984 Volume 32 Issue 7 Pages
2851-2854
Published: July 25, 1984
Released on J-STAGE: March 31, 2008
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A surgical procedure for chronic jugular vein cannulation of Gottingen miniature pig for repeated blood samplings is described. Cannulated minipigs G were used for a preliminary study of the bioavailabilities of nalidixic acid tablets showing different dissolution rates and to investigate the elimination profiles of nalidixic acid in blood after intravenous administration of the drug. The results indicate the usefulness of these catheterized minipigs G for bioavailability studies requiring fequent blood samplings.
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