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Isao Seki
1966 Volume 14 Issue 5 Pages
445-453
Published: May 25, 1966
Released on J-STAGE: March 31, 2008
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Preparation of 14-hydroxy-halo-codides (II, III), the reactions of II or III with pyrrolidine, and the acetolysis of II, III, or 14-acetoxycodeine 6-tosylate (XVI) were described with regard to steric effects of the 14β-hydroxyl group on these reactions.
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Isao Seki
1966 Volume 14 Issue 5 Pages
453-461
Published: May 25, 1966
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Preparation of 6-amino-hydrophenanthrene compounds from the 6-oxo-hydrophenanthrene compounds derived by the Hofmann degradation reaction of the 6-oxo-morphine alkaloids was described. There have been used catalytic reductive amination of the 6-oxo-compounds and catalytic, sodium borohydride, and formic acid reductions of their enamine derivatives. Behaviors of the 6-oxo-compounds in the described reactions were quite similar to those of the 6-oxo-morphines reported previously.
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Toshimitsu Ujiie
1966 Volume 14 Issue 5 Pages
461-466
Published: May 25, 1966
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8 Nitrofurans related to 2-[2-(5-nitrofuryl)vinyl]-4-quinolinecarboxylic acid and 6 Schiff bases of 5-nitrofuraldehyde were prepared and tested for their effect upon Ehrlich ascites carcinoma in mice. As the results, 2-[2-(5-nitrofuryl)vinyl]-8-quinolinol acetate and 2-[2-(5-nitrofuryl)vinyl]-4-quinolinecarboxylic acid hydrazide were shown to be very effective in inhibiting the cancer cells growth.
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Takayuki Misawa, Hiroyasu Kaneshima, Masuo Akagi
1966 Volume 14 Issue 5 Pages
467-473
Published: May 25, 1966
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1. It was found that fructose 1, 6-diphosphate and fructose 6-monophosphate were accumulated by borate in anaerobic glycolysis system of liver homogenates of guinea pigs. 2. Glyceraldehydephosphate dehydrogenase
*2 (GAP dehydrogenase) from yeast and in liver homogenates of guinea pigs and rats were found to be inhibited by borate. The inhibition was observed in both cases in which free D-glyceraldehyde or D-glyceraldehyde 3-phosphate was used as substrate. 3.GAP dehydrogenase was inhibited competitively by borate, and the inhibition was reversed by dialysis, but not reversed by excess sugars or polyhydroxy compounds in the experimental condition. 4. Borate has no effect on lactate dehydrogenase
*6 from rabbit muscle and also in liver homogenates of guinea pigs. 5. Toxicity of borate was discussed from biochemical point of view.
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Shoji Shibata, Ushio Sankawa, Heihachiro Taguchi, Kazuo Yamasaki
1966 Volume 14 Issue 5 Pages
474-478
Published: May 25, 1966
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Erythroskyrine, a nitrogen containing coloring matter of Penicillium islandicum SOPP is biosynthesized from 1 acetate (for C
(25) (26)) 9 malonate (for C
(2) (3) (9∼24)) and valine (for N
(1) C
(4∼8)).
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Tsukinaka Yamana, Yuzo Mizukami, Fujio Ichimura
1966 Volume 14 Issue 5 Pages
479-481
Published: May 25, 1966
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The kinetics hydrolysis of ethyl D-glucuronate in acid solution have been studied. It has been shown that the ester at first hydrolyzed to both D-glucuronic acid and its lactone, then they reached to equilibrium.
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Mitsuo Yamada, Akira Saito, Zenzo Tamura
1966 Volume 14 Issue 5 Pages
482-487
Published: May 25, 1966
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A fluorometric method of determination of pyridoxal-5-phosphate (PALP) and pyridoxal (PAL) in blood or organ has been developed. This method is based on Bonavita reaction of KCN with either PALP or PAL, and found to be convenient and has remarkable sensitivity for PAL as compared with the enzymatic methods. The method is also applicable to animal experiment, though it is somewhat inferior to the enzymatic methods in the sensitivity for PALP.
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Mitsuo Yamada, Akira Saito, Zenzo Tamura
1966 Volume 14 Issue 5 Pages
488-491
Published: May 25, 1966
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The specificity of the previously reported fluorometric method of determination of PALP in biological materials was investigated. The fluorescence excitation and emission spectra, the change in fluorescence intensity with pH, the electrophoresis, the paper chromatography, and the hydrolysis with acid phosphatase were examined with the PALP fraction obtained from mouse liver. The results showed that the method had high specificity for the determination of PALP in liver.
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Akira Nohara, Kin-ichi Imai, Mikio Honjo
1966 Volume 14 Issue 5 Pages
491-495
Published: May 25, 1966
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Hydrolysis of 6-benzamido-9-(2', 3', 4', -tri-O-acetyl-6'-diphenylphoshoryl-β-D-glucopyranosyl) purine (I) in alkaline solution gave 9-β-D-glucopyranosyladenine-6' phosphate (III) and -4' phosphate (IV) via the intermediate 4', 6'-cyclic phosphate. III and IV have been deaminated to give 9-β-D-glucopyranosylhypoxanthine-6' phosphate (IX) and -4' phosphate (X), respectively.
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Masashi Okada, Atsushi Yamada, Yukio Saito, Mieko Hasunuma
1966 Volume 14 Issue 5 Pages
496-501
Published: May 25, 1966
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Epoxidation of Δ
14, 16-dianhydrogitoxigenin (I) with 1.2 molar equivalents of perbenzoic acid gave 3β-hydroxy-14β, 15β-epoxy-5β-carda-16, 20 (22)-dienolide (III) which was hydrogenated over palladium-on-charcoal to afford 17α-digitoxigenin and digitoxigenin, both being obtained and identified as their acetates (IX, X). The preparation of 3β, 16β-diacetoxy-14α, 15α-epoxy-5β-carda-16, 20 (22)-dienolide (XII) from Δ
14-anhydrogitoxigenin diacetate (XI) and some reactions of XII were described.
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Shojiro Uyeo, Yoshifumi Maki, Yoshitomo Yamamoto
1966 Volume 14 Issue 5 Pages
502-505
Published: May 25, 1966
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A new compound, isopropylidenedihydrotaxinolactone, C
23H
36O
6, has been isolated as a by-product on treatment of dihydrotaxinol with acetone in the presence of toluenesulfonic acid or hydrochloric acid and shown to be represented by formula VI.
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Toshihiko Okamoto, Masaaki Hirobe, Yasunobu Tamai, Emiko Yabe
1966 Volume 14 Issue 5 Pages
506-512
Published: May 25, 1966
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N-Aminopyridinium salt (I) was reacted with cyanide ion in water at room temperature to give 2-(4-pyridyl)-s-triazolo [1, 5-α] pyridine (IV). In alkaline medium I exists as an equilibrium mixture with the ylide type, N-iminopyridine (II) which was reacted with several nitrile compounds to produce s-triazolo [1, 5-α] pyridine derivatives by 1, 3 dipolarcyclo addition. This novel triazole ring could also be synthesized by ring closure of 1, 2-diaminopyridinium salt with a carboxylic acid, acid chloride or acid anhydride. Reaction of N-methylaminopyridinium salt (XIII) or N-acetamidopyridinium salt (XIV) with cyanide ion did not afford any 1, 3-dipolar cycloaddition products. Explanation for the difference in reactivity among I, XIII and XIV was attempted from each pKa' values.
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Toshihiko Okamoto, Masaaki Hirobe, Tsuneyoshi Yamazaki
1966 Volume 14 Issue 5 Pages
512-517
Published: May 25, 1966
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N-Aminoquinolinium iodide (I) was treated with alkali in dimethylformamide to afford N-iminoquinoline dimer (II) which was further converted into N-acetimidoquinoline (III) by the reaction with acetic anhydride and successive alkaline treatment. The addition of hydroiodic acid or methyl iodide to III provided N-acetamidoquinolinium iodide (IV) or N-methylacetamidoquinolinium iodide (V) respectively. Reaction of I, IV, and V with cyanide ion was investigated. In water, I provided four products ; 4-cyanoquinoline, 2, 4-dicyanoquinoline (VI), 4-cyanoquinaldamide (VII) and 2-(4-cyano-2-quinolyl)-s-triazolo [1, 5-α] quinoline (VIII), but in methanol two products ; 4-cyanoquinoline and VII. V was also reacted in water to give a reaction intermediate, 1-methylacetamido-2-cyano-1, 2-dihydroquinoline (X VI) which was easily decomposed to 2-cyanoquinoline and N-methylacetamide quantitatively. But IV did not afford any products as above and was recovered as its ylide compound (III).
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Toshihiko Okamoto, Masaaki Hirobe, Akio Ohsawa
1966 Volume 14 Issue 5 Pages
518-523
Published: May 25, 1966
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1-(N-Methylacetamido) alkylpyridinium salt was also quite reactive to cyanide ion at its 4-position as showed in the reaction of N-methylacetamidopyridinium salt. In this paper, was reported syntheses of various N-amino derivatives of alkylpyridines and the results of the reaction of them with cyanide ion. By utilizing this reaction, it would be possible to obtain various 4-cyanoalkylpyridines without by-producing 2- or 6-cyanoalkylpyridines.
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Toshihiko Okamoto, Masaaki Hirobe, Emiko Yabe
1966 Volume 14 Issue 5 Pages
523-528
Published: May 25, 1966
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s-Triazolo [1, 5-α] pyridine ring was quite stable and showed properties similar to those of aromatic compounds. Nitration of 2-methyl-s-triazolo [1, 5-α] pyridine (IV) with potassium nitrate and sulfuric acid gave two mononitro compounds (V) and (VI). Catalytic reduction of V and VI gave the corresponding amino derivatives (VII) and (VIII) which were further converted to the corresponding bromo derivatives (IX) and (X) by the Sandmeyer reaction. But this ring was quite unstable against oxidation and fission of the pyridine ring occurred to give s-triazole derivatives.
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Atsusuke Terada, Hiroo Ito, Masatoshi Nagawa
1966 Volume 14 Issue 5 Pages
528-533
Published: May 25, 1966
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2-Bromo-3-acetoxyropiophenone (VI) was reacted with potassium phthalimide in dimethylformamide to give 2-acetoxy-3-phthalimidopropiophenone (XI). XI was submitted to hydrogenation over palladium on charcoal followed by acetylation with acetic anhydride and pyridine to yield two DL-isomers of 1-phenyl-3-phthalimide-1, 2-propanediol diacetate (XIII). Two DL-isomers of 1-(p-nitrophenyl)-3-(2, 2-dichloroacetamido)-1, 2-propanediol (I), the position isomers of chloramphenicol, were derived from XIII.
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Atsusuke Terada, Hiroo Ito, Masatoshi Nagawa
1966 Volume 14 Issue 5 Pages
533-536
Published: May 25, 1966
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The configurational investigation of the two DL-isomers of 1-(p-nitrophenyl)-3-(2, 2-dichloroacetamido)-1, 2-propanediol with were obtained as the substances of m.p. 161∼163°(Ia) and m.p. 151∼153°(Ib) in the previous study
1) was persued and Ia and Ib were assigned as threo and erythro forms respectively.
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Kazuo Achiwa, Shun-ichi Yamada
1966 Volume 14 Issue 5 Pages
537-549
Published: May 25, 1966
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The absolute configuration of (+)-isovaline ((+)-VIII) was correlated with D-(-)-quinic acid ((-)-XI) by leading to (+)-5-ethyl-5-methyl-2-pyrrolidinone ((+)-XXIX-A and B) from (+)-isovaline and D-(-)-quinic acid. It was recommended that (+)-isovaline should be shown by the formula IX or X, that is, S(+)-isovaline. The solvent effects on ORD curves of (+)-XXXI were also observed.
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Daisuke Satoh, Setsuko Kobayashi, Mieko Horie
1966 Volume 14 Issue 5 Pages
552-554
Published: May 25, 1966
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Chikara Kaneko, Sachiko Yamada
1966 Volume 14 Issue 5 Pages
555-557
Published: May 25, 1966
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Sachiko Natsume, Takanobu Itai
1966 Volume 14 Issue 5 Pages
557-560
Published: May 25, 1966
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