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Kotobuki Hano, Heitaroh Iwata, Kunihiro Nakajima
1965 Volume 13 Issue 2 Pages
107-113
Published: February 25, 1965
Released on J-STAGE: March 31, 2008
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Of the phenazine derivatives tested, phenazine-di-N-oxides produced the most marked prolongation of the survival time of mice bearing Ehrlich ascites carcinoma. Phenazine-mono-N-oxides were only moderately effective. The di-N-oxide compounds, however, were ineffective against the solid form of Ehrlich carcinoma. Other phenazine derivatives exhibited no effect on the growth of tumor cells. The degrees of inhibition of glycolysis (aerobic or anaerobic) and respiration of tumor cells by these compounds were in the same order as their antitumor activities. So, the following general structure-activity relationships were observed with the series of compounds tested : appreciable antitumor activity was found only among compounds with the 〓N→O moiety. Possible parallels between the antitumor activities of these compounds and the degrees of their inhibition of energy-generating systems of tumor cells were shown.
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Masahiro Nakadate, Yoshihiro Takano, Tadamasa Hirayama, Setsuko Sakaiz ...
1965 Volume 13 Issue 2 Pages
113-118
Published: February 25, 1965
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As a part of studies on the Janovsky reaction of nitropyridines, 3-substituted-5-nitropyridines such as 2-hydrazino-5-nitronicotinonitrile (I), 5-nitronicotinonitrile (II), 5-nitronicotinic acid (III), ethyl 5-nitronicotinate (VIII), 5-nitronicotinamide (IX), and 3-amino-5-nitropyridine (XI) were prepared. Some of their N-oxides such as ethyl 5-nitronicotinate 1-oxide (VII), 5-nitronicotinic acid 1-oxide (XII) and 5-nitronicotinonitrile 1-oxide (XV) were also prepared.
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Issei Iwai, Kazuo Tomita, Junya Ide
1965 Volume 13 Issue 2 Pages
118-129
Published: February 25, 1965
Released on J-STAGE: March 31, 2008
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The addition reaction of nitryl chloride and nitrosyl chloride with phenyl acetylene (Ia), phenylmethylacetylene (Ib), diphenylacetylene (Ic), 3-phenyl-2-propyn-1-ol alcohol acetate (Id), phenylpropiolic acid (Ie), and ethyl phenylpropiolate (If) was carried out under various conditions which afforded the corresponding chloro-nitroolefins : α-chloro-β-nitrostyrene (trans IIa and cis IIa), 1-chloro-1-phenyl-2-nitro-1-propene-1(IIb), α-chloro-β-nitrostylbene(IIc), 2-nitro-3-chloro-3-phenyl-2-propen-1-ol acetate (IId), α-nitro-β-chlorocinnamic acid (IIe), and ethyl α-nitro-β-chlorocinnamate (IIf) respectively. The geometrical relationship of the isomers of α-chloro-β-nitrostyrene were determined by dipole moments and infrared and ultraviolet spectra.
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Isuke Imada, Hiroshi Morimoto
1965 Volume 13 Issue 2 Pages
130-135
Published: February 25, 1965
Released on J-STAGE: March 31, 2008
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2-Acetoxy-3-methoxy-5-methyl-p-benzoquinone (IV) was synthesized by two methods starting from vanillin but the yield was not good in either case. The hydroquinone compound of IV was condensed with phytol and the product was hydrolyzed to give 2-hydroxy-3-methoxy-5-methyl-6-phytyl-p-benzoquinone (XI). Treatment of XI with triethylamine afforded the chromenol compound (XII), and difference in color reaction with phosphomolybdic acid of demethylubichromenol (35)(C) derived from demethylubiquinone (B) gave a powerful support to the structure of the latter (B).
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Isuke Imada, Hiroshi Morimoto
1965 Volume 13 Issue 2 Pages
136-142
Published: February 25, 1965
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1) Using the mitochondria treated with acetone, measurement was made about the activity-restoring effect of ubiquinone (35)(I) and related compounds on the succinate oxidase system, and as the partial structure required for the effect the following points were made clear : i) the quinone nucleus is necessary, ii) the methoxyl at position of 3 may be changed to a hydroxyl but if it is converted to acetoxyl the effect is lost, iii) the length of the isoprene side chain has no influence so long as the number of the isoprene is 7∼10, but when the double bonds of the side chain are saturated, the activity decreases to 1/2, and when one of the double bonds is conjugated with the quinone nucleus, the activity lowers to 1/3. 2) When added to beef-heart mitochondria, some substances in Table IV other than ubiquinone (35)(I) and ubichromenol (35) acetate (IX) show slight inhibition of the succinate oxidase system.
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Akira Takamizawa, Yoshio Hamashima
1965 Volume 13 Issue 2 Pages
142-155
Published: February 25, 1965
Released on J-STAGE: March 31, 2008
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The behaviours of 7-amino-2, 3-dimethyl- and 7-amino-2, 3, 6-trimethylpyrazolo [1, 5-α]-pyrimidines (I, II) against acylation and alkylation were investigated. Mono- and diacylates were obtained from II but only monoacylate from I, of which reason was considered due to the steric effect of the methyl group at the 6-position. The substitution position of acyl groups was confirmed to be at 7-amino group but alkyl groups at N-4 position, respectively, from their chemical and physical evidences. Their nuclear magnetic resonance and ultraviolet spectra were also discussed briefly.
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Keiji Yoshida, Tokuo Kubota
1965 Volume 13 Issue 2 Pages
156-165
Published: February 25, 1965
Released on J-STAGE: March 31, 2008
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Reactions of 17β-hydroxy-A-norandrost-3(5)-ene-1, 2-dione (Ia) and its 17-propionate (Ib) with several reagents have been examined. Treatment of I with zinc-acetic acid or lithium-liquid ammonia resulted in the reduction of only the C
1-carbonyl group giving 1β, 17β-dihydroxy-A-norandrost-3(5)-en-2-one (II). On the contrary, reaction of I with carbonyl reagents in the usual condition afforded the corresponding derivatives which were condensed at only the C
2-carbonyl group with the reagents. Lithium aluminum hydride or sodium borohydride reduction of I gave the glycols, (IV) and (V), epimeric at C-2 with the 1β-hydroxyl group.
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Keiji Yoshida, Tokuo Kubota
1965 Volume 13 Issue 2 Pages
165-172
Published: February 25, 1965
Released on J-STAGE: March 31, 2008
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Catalytic hydrogenations of the A-nor-Δ
3(5)-steroid derivatives have been described. The unsaturated 1β, 2β, 17β-(I) and 1β, 2α, 17β-(II) triols on hydrogenation with palladium-charcoal afforded afforded the saturated 1β, 17β-diol(IIIa) accompanied with hydrogenolysis of their allylic C
2-hydroxyl group, while with Adams' catalyst gave the respective trihydroxy-5β-steroids (IVa) and (VIa). The unsaturated 1β, 17β-dihydroxy-2-one (VIIa) was hydrogenated over palladium-charcoal into the corresponding 5β-steroid (VIIIa), but with Adams' catalyst to yield exclusively the 5α-steroid (XIa).
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Morizo Ishidate, Yuji Imai, Yoshinobu Hirasaka, Kenji Umemoto
1965 Volume 13 Issue 2 Pages
173-176
Published: February 25, 1965
Released on J-STAGE: March 31, 2008
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It was found that some carbohydrates with lactone group was quantitatively absorbed on anion exchange resins in aqueous solution, and by elution with suitably mineral acid they were recovered in high yield as the corresponding free acid. Thus D-glucuronic acid (II), 1, 2-O-isopropylidene-D-glucofuranosiduronic acid (V), methyl D-glucofuranosiduronic acid (VII) and L-gulonic acid (IX) were obtained advantageously from their lactone derivatives. It is noteworthy that some of them have not been obtained in success by the direct neutralization of lactone derivatives with alkaline medium.
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Yoshinobu Hirasaka, Isao Matsunaga
1965 Volume 13 Issue 2 Pages
176-179
Published: February 25, 1965
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Hepta-O-acetyl-4-O-(α-D-glucopyranosyl)-D-glucuronic acid (VII) was obtained in crystalline state by potassium permanganate oxidation of 1, 2, 3, 2', 3', 4', 6'-hapta-O-acetyl-D-maltose (VI), and by de-acetylation of VII, 4-O-(α-D-glucopyranosyl)-D-glucuronic acid (GU) was obtained. The acid hydrolysis rate of GU was also decribed.
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Masao Shimizu, Genkichi Ohta, Osamu Nagase, Seizaburo Okada, Yasuhiro ...
1965 Volume 13 Issue 2 Pages
180-188
Published: February 25, 1965
Released on J-STAGE: March 31, 2008
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A novel synthesis of pantethine (VIII) from 3-aminopropionitrile (I) was established through the intermediate formation of thiazoline derivative (IV) followed by hydrolysis thereof.
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Masao Shimizu, Yasushi Abiko
1965 Volume 13 Issue 2 Pages
189-197
Published: February 25, 1965
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1. Coenzyme A was synthesized from pantothenic acid, pantethine or S-benzoylpantetheine by rat liver extract. Biosynthesis of CoA from pantethine progressed in vitro more rapidly than from pantothenate, and a slightly lower yield of CoA was obtained when S-benzoylpantetheine was used as a substrate than when pantethine was used. 2. Pantothenate, pantethine or S-benzoylpantetheine, incorporated into a pantothenic acid-deficient diet, supported the normal growth of young rats. Tissue-CoA levels of the rats fed these diets were maintained in the normal range while the levels of the other rats, which were fed the deficient diet, were reduced by about a half. 3. Intravenous injection or oral administration of these substances into pantothenic acid-deficient rats resulted in an almost complete recovery of CoA level in the liver within 2 hours after administration.
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Keiichi Takamura, Akitoshi Shioya, Katsumaro Minamoto, Noriaki Asada, ...
1965 Volume 13 Issue 2 Pages
198-204
Published: February 25, 1965
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N-Alkyl or N, N-dialkyl 3-(substituted anilino) propionamide derivatives were prepared by several procedures. Some of these compounds were found to possess valuable analgetic and spasmolytic activities.
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Keiichi Takamura, Akitoshi Shioya, Katsumaro Minamoto, Tadahiro Yamamo ...
1965 Volume 13 Issue 2 Pages
205-210
Published: February 25, 1965
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N-Alkyl or N, N-dialkyl 3-(N'-acyl-, N'-alkyl- or N'-benzylsubstituted anilino)propionamide derivatives were prepared from corresponding N-alkyl or N, N-dialkyl 3-(substituted anilino) propionamides by treating with acid anhydride, alkylhalide, or formaldehyde, formic acid and benzyl chloride, respectively. N, N-Dialkyl 3-(substituted anilino) propylamines were also prepared by condensation of 3-(substituted anilino) propyl chlorides with secondary amines. N, N-Dialkyl 3-(N'-acyl-substituted anilino) propylamines were obtained by treatment of 3-(substituted anilino) propylamines with acid anhydrides. Some of these compounds were found to possess analgetic activities.
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Keiichi Takamura, Akitoshi Shioya, Tadahiro Yamamoto, Shin-ichi Takama ...
1965 Volume 13 Issue 2 Pages
211-217
Published: February 25, 1965
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N, N-Dialkyl 3-(substituted anilino) butyramides were prepared by condensing of N, N-dialkyl crotonamides or N, N-dialkyl 3-chlorobutyramides with substituted anilines. N, N-Dialkyl 3-(N'-benzyl-substituted anilino) butyramides were prepared from N, N-dialkyl 3-(substituted anilino) butyramides and benzyl chloride. Some of the compounds thus prepared have analgetic activities.
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Hideo Yamaguchi, Kuniko Nishimoto
1965 Volume 13 Issue 2 Pages
217-220
Published: February 25, 1965
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Systematic extraction and isolation of alkaloids were carried out on Physalis alkekengi L.var franchettii HORT forma bunyardii MAKINO. Besides two alkaloids, there was obtained an oily base, C
13H
21O
2N, as a chief alkaloid, which was confirmed to be 3α-tigloyloxytropane (I) as a result of detailed examinations.
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Morio Ikehara, Hitoshi Uno
1965 Volume 13 Issue 2 Pages
221-223
Published: February 25, 1965
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Shun-ichi Yamada, Shiro Terashima, Kazuo Achiwa
1965 Volume 13 Issue 2 Pages
227-229
Published: February 25, 1965
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Bunji Shimizu, Motoji Asai, Takuzo Nishimura
1965 Volume 13 Issue 2 Pages
230-232
Published: February 25, 1965
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