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KIYOSHIGE OCHI, KATSUHITO MIYAMOTO, YUTAKA MIURA, HIROKI MITSUI, ISAO ...
1985 Volume 33 Issue 4 Pages
1703-1706
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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A facile synthetic method for pyrimidine acyclonucleosides is described. Bis (trimethylsilyl) ethers of uracils (1-3) react with 2-substituted 1, 3-dioxolanes (4) in the presence of a Lewis acid to form 1-[α-(2-hydroxyethoxy) alkyl] uracil derivatives. Treatment of these reaction mixtures with methanol containing sodium hydrogen carbonate or aqueous sodium hydroxide gives pyrimidine acyclonucleosides (5a-g).
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MIKIO HORI, EIJI IMAI, NORIHIRO KAWAMURA, TATSUNORI IWAMURA, TADASHI K ...
1985 Volume 33 Issue 4 Pages
1707-1710
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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In order to study the effects of N-substituents of benzomorphans on antagonist-agonist activity we synthesized several benzomorphan derivatives having N-alkenyl, alkynyl, pyranyl or oxetanylmethyl groups. Reduction of N-(hepta-2, 5-diyn-4-yl) benzomorphan (13) with Lindlar catalyst resulted in dealkylation to afford normetazocine (1), whereas reduction with diisobutylaluminum hydride gave N-(hept-2-en-5-yn-4-yl) benzomorphan (17). N-Dihydro-(14) and tetrahydropyran derivatives (15) were obtained by the reaction of 1 with 4-methoxypyrylium salt followed by reduction with sodium borohydride.
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YOSHIHIRO NITTA, YASUSHI ARAKAWA
1985 Volume 33 Issue 4 Pages
1711-1715
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Recently, it has been reported that the treatment of amino acids with alkyl p-toluenesulfonates in alcohol affords the p-toluenesulfonates of the corresponding alkyl esters in high yields. The results of our examination of this reaction indicated that the reaction proceeds predominantly through the general acid-catalyzed esterification of carboxylic acid by alcohol, and the involvement of transesterification is minor.
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TOZO FUJII, MASASHI OHBA, SHIGEAKI AKIYAMA
1985 Volume 33 Issue 4 Pages
1716-1720
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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In boiling 2.5 N solution of KOH in 40% (w/w) aqueous EtOH, the lactams (±)-5a, b, d were hydrolyzed to an extent of 75-98% within 8-20 h, attaining equilibrium with the corresponding ω-amino acid derivatives (±)-6a, b, d. The potassium salt (±)-8, generated in situ from the translactam acid (±)-7, was equilibrated with the ring-opened product (±)-6f and the recyclized cis isomer (±)-5f in a ratio of 57 : 15 : 28 within ca. 45 h under similar reaction conditions. The cis-N-(2-arylethyl) analog (-)-9 was converted into the trans-lactam acid (+)-13, a key synthetic precursor for the 8-hydroxy-9, 10-dimethoxybenzo [a] quinolizidine-type Alangium alkaloids, through application of such alkaline hydrolytic cis-trans equilibration followed by debenzylation.
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YUICHI KANAOKA, TETSUO TAKAHASHI, HITOSHI NAKAYAMA, KAZUTAKA TANIZAWA
1985 Volume 33 Issue 4 Pages
1721-1724
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Two 7-amino-4-methylcoumarinamide derivatives of tripeptides were synthesized. They were shown to be potentially useful substrates for fluorometric microdetermination of subtilisins BPN'and Carlsberg. The kinetic characteristics of the hydrolyses of these substrates by the enzymes were investigated.
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SHIZUO TODA, TOSHIO MIYASE, HIDEKO ARICHI, HISAYUKI TANIZAWA, YOSHIO T ...
1985 Volume 33 Issue 4 Pages
1725-1728
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Antioxidative components in the methanol extract of the rhizome of Curcuma longa L. were investigated by using our evaluation method based on the air oxidation of linoleic acid. Curcuminoids such as curcumin, 4-hydroxycinnamoyl (feruloyl) methane and bis (4-hydroxycinnamoyl) methane were found to be active components. Curcumin was the most active component and its 50% inhibitory concentrations for the air oxidation of linoleic acid were 1.83×10
-2% (thiobarbituric acid value) and 1.15×10
-2% (peroxide value). These values of curcumin are superior to those of dl-α-tocopherol.
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TOYOSHIGE ARAKI, JUNKO HIROGUCHI, HISAMI MATSUNAGA, YUKIO KIMURA
1985 Volume 33 Issue 4 Pages
1729-1733
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Asolectin, a commercial crude phosphatidylcholine, which is known to inhibit the antibacterial activity of polymyxins, was studied to identify the main inhibiting substance. It was separated into several fractions by using high performance liquid chromatography (HPLC) on LiChrosorb SI 60, and each fraction was tested for effect on the antibacterial activity of colistin sulfate, one of the polymyxin group antibiotics. Most of these fractions showed various degrees of inhibiting effect but, conversely, one fraction (corresponding to lysophosphatidylcholine) potentiated the antibacterial activity of colistin. With authentic samples we confirmed that lysophosphatidylcholine showed a potentiating effect on the antibacterial activity of colistin, polymyxin B and polymyxin M. These results suggest that some detergents may be useful as potentiators of the antibacterial activity of polymyxins.
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KAZUHIKO JUNI, JUNKO OGATA, NORIKO MATSUI, MIHO KUBOTA, MASAHIRO NAKAN ...
1985 Volume 33 Issue 4 Pages
1734-1738
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Polylactic acid (PLA) microspheres containing aclarubicin were prepared by a solventevaporation process and their release patterns were examined in vitro. When microspheres were prepared with the drug and PLA, the release rates of the drug were extremely small. When microspheres were prepared with fatty acid esters as additives, the release rates of the drug were significantly increased depending on the amount of the additive incorporated. Two additives, isopropyl myristate and medium-chain triglyceride, exhibited similar effects on the steady-state release rates of the drug from the microspheres. In addition, the effect of alkyl chain length of the additives on the release rate of the drug was examined by using a series of ethyl and butyl esters of fatty acids. A parabolic relationship was obtained between the steady-state release rate of the drug and the alkyl chain length of the additives. Therefore the release rate of the drug could be controlled by proper selection of the additive and by adjusting the amount of the additive used in the preparation of the microspheres.
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EIKO MATSUMURA, TAKASHI SHIN, SAWAO MURAO, SATOSHI YOMODA, TATSU KAWAN ...
1985 Volume 33 Issue 4 Pages
1739-1744
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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"N
α-Benzyloxycarbonyl amino acid urethane hydrolase III" was purified from the cell-free extract of Lactobacillus casei ε ATCC 7469. The enzyme was purified 583-fold with an activity yield of 50%, and its homogeneity was confirmed by polyacrylamide gel electrophoresis. The molecular weight of the native enzyme is about 230000, and the isoelectric point is 4.60. The enzyme activity was inhibited by p-chloromercuribenzoic acid (PCMB) and dithiothreitol (DTT). The presence of divalent cations (i.e., Co
2+ or Zn
2+) is essential for its activity. The enzyme catalyzed the hydrolysis of the urethane bonds of Z-Gly, Z-Ala and Z-Ser.
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Yoshisuke Tsuda, Shinzo Hosoi
1985 Volume 33 Issue 4 Pages
1745-1748
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Acidic phenylselenenylation of O-methylestrone with PhSeCl and BF
3.Et
2O gave an α-phenylselenenylketone and an α-chloro-α-phenylselenenylketone, both of which were converted to the same α, α-dimethoxyketone on treatment with mercury (II) perchlorate in methanol. Hydride reduction of this, dithiocarbonylation of the resulting product followed by acid hydrolysis, and treatment with tributyltin hydride gave O-methylisoestrone, the 1, 2-carbonyl transposed product, in overall yield of 75%.
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Shigeyuki Yoshifuji, Kenichi Tanaka, Yoshihiro Nitta
1985 Volume 33 Issue 4 Pages
1749-1751
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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The oxidation of N, C-protected L-2, 4-diaminobutyric acid, L-ornithine and L-lysine with RuO
4 gave the corresponding L-asparagine, L-glutamine and L-2-aminoadipic acid 6-amide derivatives, respectively.
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Naoki Sakura, Kyoko Hirose, Tadashi Hashimoto
1985 Volume 33 Issue 4 Pages
1752-1755
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Novel L-asparagine and L-glutamine derivatives with the carboxamide nitrogen (N
ca) acylated by urethane type protecting groups, tert-butyloxycarbonyl (Boc) and 4-nitrobenzyloxycarbonyl [Z(NO
2)], were synthesized through ruthenium tetroxide oxidative transformation of N
α, N
ω-diacylated L-2, 4-diaminobutyric acid and L-ornithine. N
ca-Boc and N
ca-Z (NO
2) groups can be deprotected by trifluoroacetic acid and catalytic hydrogenation respectively. N
α, N
ca-DiBoc-Asn-OH is applied to peptide synthesis by dicyclohexylcarbodiimide or mixed anhydride method without nitrile formation.
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Mochammad Sholichin, Kazumoto Miyahara, Toshio Kawasaki
1985 Volume 33 Issue 4 Pages
1756-1759
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Seven compounds, scillascilloside D-1, E-1∼-5, and G-1 were obtained in pure state from the fresh bulbs of Scilla scilloides and characterized. They are oligoglycosides of the spirocyclic nortriterpenoids related to eucosterol.
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Toshio Takahashi, Chikako Shimizu, Shinichi Nakamoto, Kiyoshi Ikeda, K ...
1985 Volume 33 Issue 4 Pages
1760-1762
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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New development of a general key-intermediate for synthesis of lipid A and related compounds and its conversion into lipid X are described.
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Miyoji Hanaoka, Hiroshi Yamagishi, Chisato Mukai
1985 Volume 33 Issue 4 Pages
1763-1765
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Regioselective demethylation of oxychelerythrine (5), derived from berberine (4), with p-toluenesulfonic acid in refluxing toluene gave oxyfagaridine (6), which was converted into fagaridine (1) in good yields by successive reduction and oxidation.
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Akira Matsuda, Misao Shinozaki, Tadashi Miyasaka, Haruhiko Machida, To ...
1985 Volume 33 Issue 4 Pages
1766-1769
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Reaction of 2-iodoadenosine (2) with terminal alkynes in the presence of bis (triphenylphosphine) palladium dichloride and cuprous iodide in triethylamine and N, N, -dimethylformamide gave 2-alkynyl-adenosines (3a-h) in excellent yields. Several compounds showed high activity as inhibitors in rat passive cutaneous anaphylaxis (PCA) reaction. Among them, 2-(3-hydroxypropynyl)- and 2-(3-hydroxybutynyl)-adenosines (3d, f) are much more potent than disodium cromoglycate (DSCG).
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Takeshi Kinoshita, Shigeru Tatara, Ushio Sankawa
1985 Volume 33 Issue 4 Pages
1770-1773
Published: April 25, 1985
Released on J-STAGE: March 31, 2008
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Two new indoles named paniculidines A and B were isolated from Murraya paniculata (Linn.) Jack., and their structures have been elucidated as methyl 2-methyl-4-(indol-3-yl)-butyrate and 2-methyl-4-(1-methoxyindol-3-yl)-1-butanol, respectively.
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