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Seigoro Hayashi, Hiroshi Ueki, Seiko Harano, Junko Komiya, Susumu Iyam ...
1964 Volume 12 Issue 11 Pages
1271-1276
Published: November 25, 1964
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Dimethanesulphonylthioalkanes and analogous compounds were synthesized by the reaction of corresponding sodium thiosulphonate and appropriate dibromide to test the carcinostatic activity compaed with Myleran. It was found that some of these compounds inhibited pronouncedly the growth of the solid tumor produced by Ehrlich ascites carcinoma cells.
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Masahiro Nakadate, Takatsune Maki, Michiya Kimura
1964 Volume 12 Issue 11 Pages
1276-1281
Published: November 25, 1964
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A sensitive and accurate colorimetric determination for urinary creatinine is described. The principle of this method is based on the reaction of creatinine with 2, 2', 4, 4'-tetranitrobiphenyl in the presence of potassium hydroxide to give a stable color which shows no photo- and temperature-sensitity and is measured spectrometrically at 555 mμ. The applicable concentration range is 0 to 200 μg./ml. of creatinine. No interferences were shown by considerably larger amounts of acetone, glucose, ascorbic acid, pyruvic acid, and dehydroepiandrosterone.
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Toshihiko Ariyoshi, Eigo Takabatake
1964 Volume 12 Issue 11 Pages
1281-1285
Published: November 25, 1964
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Malonic acid derivatives having cyclohexene ring were prepared and their effects on the metabolism of EHB in the rat liver preparation were examined. In the female rats pretreated with cyclohexenylethylmalonamic acid ethyl ester (VI), cyclohexenylethylmalonic acid diamide (VII), 2-cyclohexenyl-2-ethylacetamide (VIII), and cyclohexenylethylacetylurea (IX), the duration of EHB-hypnosis was shortened and the EHB-metabolizing activity of liver homogenate was stimulated. On the other hand, the duration of EHB-hypnosis was prolonged and the metabolizing activity was inhibited by pretreatment with 2-(diethylamino) ethyl cyclohexenylethylacetate hydrochloride (X) or N-[2-(diethylamino) ethyl]-2-cyclohexenyl-2-ethylacetamide oxalate (XI).
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Toshihiko Ariyoshi
1964 Volume 12 Issue 11 Pages
1286-1289
Published: November 25, 1964
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Various 1-methyl- and 1, 3-dimethybarbiturates were prepared and their stimulatory effect on EHB-metabolism in the rat liver preparation were examined. The pretreatment of female rats with original barbiturates markedly accelerated the EHB-metabolism than that with 1-methylbarbiturates, and 1, 3-dimethylbarbiturates treatment had not such a stimulatory effect. It was demonstrated that such stimulatory effect of various N-substituted barbiturates on EHB-metabolism would be related to the substitution of N-position of barbituric acid ring.
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Shiro Takahashi, Hideo Kano
1964 Volume 12 Issue 11 Pages
1290-1295
Published: November 25, 1964
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1-Methylbenzimidazole 3-oxide reacted with phenyl isocyanate, phenyl isothiocyanate, dimethyl acetylenedicarboxylate, and methyl propiolate, at room temperature and with benzonitrile, phenyl isocyanide, and benzyne on heating to give 1-methyl-2-anilino-benzimidazole (II), II, dimethyl 1-methyl-2-benzimidazoloxalacetate, methyl α-formyl-1-methyl-2-benzimidazolacetate, 1-methl-2-benzamidobenzimidazole, II, 1-methyl-2-(ο-hydroxyphenyl) benzimidazole, respectively. Although the initial cycloadducts could not be isolated, these reactions can be best explained as occurring via 1, 3-dipolar cycloaddition.
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Yoshio Ban, Masako Seo
1964 Volume 12 Issue 11 Pages
1296-1301
Published: November 25, 1964
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The total synthesis of alstoniline, an alkaloid of Alstonia constricta F. MUELL, was achieved by applying a new synthetic method of β-carboline derivatives which has been being developed in this laboratory.
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Hiroshi Nakamura, Setsuzo Tejima, Masuo Akagi
1964 Volume 12 Issue 11 Pages
1302-1307
Published: November 25, 1964
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The works on the bromination of 3, 4, 6-tri-O-acetyl-D-glucal and methanolysis of the product which had been reported by Fischer, Bergmann, and Schotte (Ber., 53, 509 (1920)) were restudied. The strctures of the two crystalline compounds termed the "triacetyl-methylglucoside-2-bromohydrins I and II" were demonstrated as methyl 2-bromo-2-deoxy-3, 4, 6-tri-O-acetyl-β-D-glucopyranoside and methyl 2-bromo-2-deoxy-3, 4, 6-tri-O-acetyl-β-D-mannopyranoside, respectively. 2-Bromo-2-deoxy-1, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranose (X) was prepared as a crystalline form. Crystalline, stable bromide (XI) was prepared starting from X, and assigned as 2-bromo-2-deoxy-3, 4, 6-tri-O-acetyl-α-D-glucopyranosyl bromide which was not identical with the labile bromide by Fischer, et al. The nuclear magnetic resonance spectra presented a further proof for the configurations at C1 and C2 in X and XI.
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Tsutomu Momose, Yo Ueda, Chiharu Nakakura
1964 Volume 12 Issue 11 Pages
1307-1311
Published: November 25, 1964
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Free cholesterol in blood serum was extracted with acetone-ethanol, precipitated with digitonin, and developed with perchloric acid-phosphoric acid-ferric chloride reagent, which was previously used for the determination of total cholesterol in serum.
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Toshio Kawasaki, Itsuo Nishioka
1964 Volume 12 Issue 11 Pages
1311-1315
Published: November 25, 1964
Released on J-STAGE: March 31, 2008
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As the leaf saponins of Digitalis purpurea L. two saponins, I and II, were detected on a paper chromatogram and isolated by column chromatography on alumina. With the aid of thin-layer chromatography I was found to be composed of two saponins, I-1 and I-2, while II to be a mixture of six (three pairs). I-1 and I-2 were obtained in pure state according to the Tschesche method and characterized, respectively, as tigogenin- and gitogenin-tetraglycosides both of which equally have one mole each of D-galactose and D-xylose and two moles of D-glucose as the sugar moieties. I-1, m.p. 284∼286°(decomp.), [α]
28D-64.0°, was named desgalactotigonin and I-2, m.p. 252∼255°(decomp.), [α]
25D-58.5°, F-gitonin. Three pairs of saponins in II were assumed to be penta-, hexa- and hepta-glycosides and each pair was presumed to consist of tigogenin- and gitogenin-glycosides both of which might have the same sugar composition.
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Masaaki Horiguchi, Mitsuo Ishida, Nobuyuki Higosaki
1964 Volume 12 Issue 11 Pages
1315-1319
Published: November 25, 1964
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Gas chromatography was successfully applied to the separation of a mixture of nine organophosphorous insecticides using three different column under varying conditions. This method was applicable to the quantitative analysis of commercial Malathion dusts and provided results comparable to the colorimetric estimation.
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Kazukichi Kato
1964 Volume 12 Issue 11 Pages
1319-1328
Published: November 25, 1964
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The mechanism of the new color reaction of steroid has been studied on cholesterol. In this reaction, cholesterol is changed at first by anhydrous aluminum chloride into cholesteryl chloride and then into cholest-3, 5-diene. Colorimetric and chromatographic investigations reveal that they are intermediates from cholesterol to the next step of the reaction. A colorless species obtained from cholesteryl chloride and anisaldehyde gives a characteristic color with anhydrous aluminum chloride or other Lewis acid. For this colorless reaction product, a benzal type structure conjugated with double bonds in rings of the steroid is postulated, and a mechanism based on the Prins reaction is proposed, for which a support is obtained from the spectroscopic data in comparison with a reaction product of cholest-5-ene. It is concluded that the coloration may be due to a coupling of the reaction product with Lewis acid which gives rise to resonance structures.
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Tadashi Sasaki, Katsumaro Minamoto
1964 Volume 12 Issue 11 Pages
1329-1338
Published: November 25, 1964
Released on J-STAGE: March 31, 2008
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Im Rahmen der Untersuchungen der Synthesemoglichkeit von as-Triazin-N-oxyden, oxydierten wir 3-Amino- bzw. 3-Amino-5, 6-dimethyl-as-triazin durch Persaure, wobei sich die entsprechenden 5-Oxo-verbindungen und ein Mono-N-oxyd von 3-Amino-5, 6-dimethyl-as-triazin erhalten lieβen, deren Konstitutionen bzw. diejenigen der acetylierten Korpern durch Dipolmoment-Messungen sowie spektroskopisch diskutiert wurden.
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Tetsuo Miyadera, Issei Iwai
1964 Volume 12 Issue 11 Pages
1338-1343
Published: November 25, 1964
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Quinolizinium bromide (IVa) was prepared in good yield from commercially available ethyl picolinate and γ-butyrolactone. This synthetic route is convenient for synthesis of the parent compound (VIa) and was extended to preparations of the monomethyl derivatives (IVb∼d, VII).
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Tetsuo Miyadera, Eiji Ohki, Issei Iwai
1964 Volume 12 Issue 11 Pages
1344-1351
Published: November 25, 1964
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Quinolizinium bromide (V) reacts with warious Grignard reagents giving two geometric isomers of ring opened products respectively. The reaction intermediate would be a 4-substituted-4H-quinolizine derivative (IV) which rearranges to the more stable pyridine derivative (i.e., VIII).
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Fumio Yoneda, Takayuki Ohtaka, Yoshihiro Nitta
1964 Volume 12 Issue 11 Pages
1351-1356
Published: November 25, 1964
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Durch die Einwirkung von phenacylbromiden auf 3-Amino-6-chlorpyridazin wurden verschiedenartige 2-Phenyl-6-chlorimidazo [1, 2-b] pyridazine hergestellt. Das Chloratom der letzteren wurde durch Einwirkung von Na-Alkoholaten, Dialkylaminen bzw. wasr. alkoholischem Kali gegen Alkoxyl-, Dialkylamino- bzw. Hydroxyl-gruppen ausgetaus ht.
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Kyosuke Tsuda, Susumu Ikuma, Masaaki Kawamura, Ryuji Tachikawa, Kiyosh ...
1964 Volume 12 Issue 11 Pages
1357-1374
Published: November 25, 1964
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The structures of both tetrodonic acid hydrobromide and 6, 11-diacetylanhydrotetrodotoxin hydroiodide were established by chemical and X-ray crystallographical research. Based upon structures of both these salts and upon other chemical information, we determined that tetrodotoxin and anhydrotetrodotoxin have zwitterionic hemilactal structures.
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Kazuo Sugimoto, Sadao Ohki
1964 Volume 12 Issue 11 Pages
1375-1378
Published: November 25, 1964
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Aromatic nitrogen mustards containing an azo group (VII∼XV), a nitrogen mustard with a carrier and masking group, were synthesized in one step starting from p-amino-phenylalanine or aliphatic p-amino-phenyl acid.
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Yoshio Ban, Masako Seo
1964 Volume 12 Issue 11 Pages
1378-1380
Published: November 25, 1964
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1-Methyl-1, 2, 3, 4, 7, 8-hexahydro-13H-benz [g] indolo [2, 3-a] quinolizinium salt (VIII, R=CH
3) was synthesized from 3-chloro-5-methyl-5, 6.7, 8-tetrahydroisoquinoline (Va), in which case the intermediary quaternary bromide (VIIa) was isolated.
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Yoshio Ban, Ichizo Inoue
1964 Volume 12 Issue 11 Pages
1381-1383
Published: November 25, 1964
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3-Ethyl-10-methoxy-12H-indolo [2, 3-a] quinolizinium chloride might be called "10-methoxy-flavopereirine hydrochloride, " which was synthesized by the method developed in this laboratory with some expectation that this compound would at some time be found in nature.
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Zenzo Tamura, Toshio Imanari
1964 Volume 12 Issue 11 Pages
1386-1388
Published: November 25, 1964
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Matsuo Mitsuyoshi, Mikio Yamazaki
1964 Volume 12 Issue 11 Pages
1388-1389
Published: November 25, 1964
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Masahiko Fujino, Takaaki Kamiya, Hidesuke Iwasaki, Jisaburo Ueyanagi, ...
1964 Volume 12 Issue 11 Pages
1390-1392
Published: November 25, 1964
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Seigoro Hayashi, Hiroshi Ueki, Kimio Hamamura, Mizuyo Tsukada
1964 Volume 12 Issue 11 Pages
1393-1394
Published: November 25, 1964
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Yoshio Arata
1964 Volume 12 Issue 11 Pages
1394-1395
Published: November 25, 1964
Released on J-STAGE: March 31, 2008
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