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Minoru Sekiya, Toshio Oishi
1959 Volume 7 Issue 8 Pages
855-857
Published: December 20, 1959
Released on J-STAGE: March 31, 2008
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It was found that aromatic aldehyde, N-arylmethylenealkylamine, and formamide react together to give N-arylmethylene-1-formamido-1-arylmethylamine. Benzaldehyde and p-chlorobenzaldehyde were used as reactants with the corresponding N-arylmethylenealkylamine. By using benzaldehyde and N-(p-methoxybenzylidene) methylamine, N-(p-methoxybenzylidene)-α-formamidobenzylamines containing different aryl groups were obtained.
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Tsutomu Momose, Yo Ueda, Shujiro Goya
1959 Volume 7 Issue 8 Pages
858-861
Published: December 20, 1959
Released on J-STAGE: March 31, 2008
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Ultraviolet absorption of 47 benzenesulfonamide derivatives was measured in 95% ethanol. Both electron-donating and -attracting groups in the para-position of sulfon-amide group effected a shift to longer wave lengths. The correlation of displacement of the absorption maxima with the electronic character of substituents was discussed, and approximately linear relation of the shift with Hammett's σ was found in electron donating groups.
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Tsutomu Momose, Yo Ueda, Shujiro Goya
1959 Volume 7 Issue 8 Pages
862-863
Published: December 20, 1959
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Ultraviolet absorption spectra of phenyl methyl sulfone derivatives were compared with those of benzenesulfonamide derivatives. Introduction of an electron-donating group in the para-position of phenyl methyl sulfone causes a larger bathochromic shift of the first primary band than that in the para-position of benzenesulfonamide, whereas the introduction of electron-attracting group gives hypsochromic shift from the corresponding benzenesulfonamide. Effect of substituents attached to the methyl group of methyl-sulfones on the spectra was also discussed.
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Tsutomu Momose, Shujiro Goya
1959 Volume 7 Issue 8 Pages
864-866
Published: December 20, 1959
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The Fries rearrangement of 5, 8-dimethoxy-1-naphthol acylate gave 2-acyl-5, 8-dimethoxy-1-naphthol in a yield of 24∼56%. These acyl compounds were demethylated and oxidized to 5-hydroxy-6-acyl-1, 4-napthoquinones.
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Eiichi Matsui
1959 Volume 7 Issue 8 Pages
867-872
Published: December 20, 1959
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Mercapto compounds were tested as to their chemical reactivity with nitrogen mustard (HN
2) and its N-oxide (HN
2-O) in vitro, and as to their preventive action in vivo against rat leucopenia induced by the same agents. Of these compounds, L-cysteine alone was found to show remarkable activity in vivo, while D-cysteine and L-cysteine methyl ester were proved to be only slightly effective. Administration of L-cysteine 30 min. after HN
2-O injection prevented to some extent the leucopenia of Yoshida sarcoma rats without being deprived of its anti-tumor effect.
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Morizo Ishidate, Yoshio Sakurai, Hiroshi Imamura, Ayako Moriwaki
1959 Volume 7 Issue 8 Pages
873-877
Published: December 20, 1959
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A new and simplified method for screening of antitumor substances with in vitro-cultured tumor cells is presented. The effect of the test compound is determined by observation of the delayed appearance and long-lasting cytomorphological change of the cells through 72 hours of incubation. The method is especially suitable for sereening of antimitotic or radiomitotic substances, because the real characteristic damage on nuclei can be discriminated from an acute unspecific cytotoxicity. By this technique, it is possible to avoid the error of taking a depression of growth rate caused by a mere cytolysis or by direct destruction as an index of the true anti-tumor effectiveness.
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Nobuo Suzuki, Kiyoshi Tsukida
1959 Volume 7 Issue 8 Pages
878-883
Published: December 20, 1959
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1. When submitted to some thermal and photochemical treatments, luteochrome, C
40H
56O
2, suffers partial trans-cis isomerization and rearrangement into aurochrome. By means of chromatography a quantitative study of the resulting complex mixture was possible. 2. All-trans luteochrome was more stable to thermal and photochemical treatments than all-trans-β-carotene mono- and di-epoxides. However, considerable amount of stereoisomerization occurred when subjected to some treatments such as illumination in the presence of iodine or melting of crystals. 3. Luteochrome yielded four kinds of cis forms whose spectral characteristics were studied and their tentative configurational assignments were made. Some of these isomers were adsorbed on a chromatographic column, above or below the corresponding all-trans form. None of the cis forms crystallized.
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Makoto Yokoo
1959 Volume 7 Issue 8 Pages
884-886
Published: December 20, 1959
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Pyridine was determined by catalytic reduction over Raney nickel and subsequent azotometry of secondary amines. Catalytic reduction of pyridine was completed merely by shaking it with Raney nickel W-6 in a test tube, omitting the general procedure of introducing hydrogen. Thus, pyridine, isonicotinic acid, N-hydroxymethyl-isonicotinamide, and 2-benzyl-aminopyridine was determined with an accuracy within 1.3%.
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Hiroshi Tanida
1959 Volume 7 Issue 8 Pages
887-891
Published: December 20, 1959
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2-Aminoquinoline 1-oxide gave 6-tosyloxy-2-aminoquinoline by rearrangement with tosyl chloride in 49% yield. A small quantity of an isomeric by -product (7%), which was considered to be 3-tosyloxy-2-aminoquinoline, was not identified.
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Sadao Ohki, Ichiro Matuo
1959 Volume 7 Issue 8 Pages
892-895
Published: December 20, 1959
Released on J-STAGE: March 31, 2008
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In expectation of a curariform activity with little side effects, methiodide of 3, 3'-polymethylenediquinolizidines (I : n=4, 6, 8, and 10) were synthesized. Condensation of the potassium salt of 3-ethoxycarbony1-4-oxoquinolizidine and polymethylene bromide, followed by saponification and decarboxylation, and reduction with lithium aluminum hydride of the lactam compound so obtained afforded the objective compounds (I). (I : n=4) was also obtained through 3-(4-phenoxybutyl) quinolizidine (IX) as an intermediate and compounds obtained by the two procedures were found to be identical. The curariform activity of (I) (n=4 and 6) was one-quarter that of tubocurarine chloride while their toxicity was 6 and 10 times, respectively, of tubocurarine. The compound with n=10 had a strong antibacterial and antifungal activity.
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Katsura Morita, Shunsaku Noguchi, Masamoto Nishikawa
1959 Volume 7 Issue 8 Pages
896-897
Published: December 20, 1959
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An equimolar complex of dimethylformamide and phosgene, which is readily formed in situ or in dry benzene from the components with concomitant loss of carbon dioxide, was found to be an excellent formylating agent for steroid alcohols. A mechanism of the reaction was proposed and the yield of the formyl esters are given for a number of steroids.
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Tokuo Kubota
1959 Volume 7 Issue 8 Pages
898-902
Published: December 20, 1959
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Kogagenin diacetate (IV) has been correlated to the known yonogenin diacetate (XIVb) and the acetoxyl groups in the former were proved to be located at C-2 and C-3. The structure of the carbonate of kogagenin diacetate was also established. Consequently, the structure of kogagenin has been confirmed as 25D-spirostane-1β, 2β, 3α, 5β-tetrol (I) as proposed earlier.
1) Also, the reaction of kogagenin with phosgene was investigated and it was found that phosgene rather predominantly reacts with a cis-α-glycol than a diaxial 1, 3-glycol in kogagenin.
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Hideo Kano, Yasuo Makisumi, Shiro Takahashi, Masaru Ogata
1959 Volume 7 Issue 8 Pages
903-906
Published: December 20, 1959
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Halogenation of 5-methyl-7-hydroxy- and 5-methyl-7-amino-s-triazolo [2, 3-a] pyrimidines with chlorine or bromine gave teh corresponding 6-halogeno derivatives (IX), (X), (XIII), and (XIV). 5-Methyl-6-halo-7-hydroxy derivatives (IX and X) were transformed to the corresponding 6-halo-7-chloro derivatives (VI and XI), which were converted into some 7-substituted 6-halogeno derivatives (XIII, XIV, XV, and XVI) by the usual nucleophilic substitution. Some of these compounds showed biological activity.
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Yasuo Makisumi, Hideo Kano
1959 Volume 7 Issue 8 Pages
907-911
Published: December 20, 1959
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Six kinds of 7-substituted s-triazolo [2, 3-a] pyrimidines, which are related to some isomeric compounds of natural purines and their antagonists, were prepared. Halogenation of 7-hydroxy- and 7-amino-s-triazolo [2, 3-a] pyrimidines with chlorine or bromine gave the corresponding 6-halogeno derivatives (VII), (VIII), (XI), and (XII). Some other 7-substituted 6-halogeno derivatives (XI), (XII), (XIII), and (XIV) were also derived from (IX) and (X) by the usual substitution reactions. Some of these compounds showed biological activity.
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Kyozo Hayashi
1959 Volume 7 Issue 8 Pages
912-916
Published: December 20, 1959
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It has previously been reported that aliphatic amino acid was obtained from alkylmalonic acid using the Schmidt reaction, in a good yield. In this report the synthesis of more than twenty kinds of phenylalanine analogs from arylmalonic acid is described and furthermore, the effect of the benzene ring and its substituents on the reaction was examined, and some new information were obtained. 1) When the group of malonic acid combines directly with the benzene ring, the yield was considerably good. 2) In the case of benzylmalonic acids, when the electronegative group exists in the benzene ring, the expected amino acid was obtained, though in a low yield, but in the case with the positive group in the benzene ring, the expected amino acid was scarcely obtained. 3) From benzylmalonic acid the yield of amino acid was 18%, but from cyclohexyl-ethylmalonic acid, the yield of cyclohexylalanine was 50%.
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Torizo Takahashi, Mikio Hori, Akio Kanbara
1959 Volume 7 Issue 8 Pages
917-920
Published: December 20, 1959
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A new synthetic route for N, N-dimethyl-1-m-hydroxyphenylcyclohexaneethylamine (IX) from ethyl cyclohexylidenecyanoacetate is described. 1-(m-Methoxyphenylcyclohexyl) trimethylamine (XII) was prepared by the Curtius degradation of 1-m-methoxyphenyl-cyclohexaneacetic acid (V) and subsequent dimethylation.
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Goro Chihara, Keiichi Tanikawa
1959 Volume 7 Issue 8 Pages
920-924
Published: December 20, 1959
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A new analytical procedure using infrared absorption spectra was established for determination of compounds containing heavy nitrogen (
15N). This procedure is a combination of the Kjeldahl method and gas determination by infrared spectrum. Compounds containing heavy nitrogen is converted to ammonia, and qualitative and quantitative analyses are carried out after determination of key bands of
15NH
3 from the difference between
14NH
3 and
15NH
3 in the symmetric deformation vibration of NH
3 in the region of 800∼1200 cm
-1. Precision of the present procedure is somewhat lower than that by mass spectrometer but the procedure is far more simple and will be effective for various experiments using heavy nitrogen (
15N).
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Toshihiko Okamoto, Hideo Tani
1959 Volume 7 Issue 8 Pages
925-930
Published: December 20, 1959
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N-Alkoxypyridinium derivatives were reacted with potassium cyanide and 2- and 4-cyanopyridines were obtained as the reaction product. This reaction was proved to be a universal reaction for quaternary salts of N-oxides of pyridine and substituted pyridines including quinoline and isoquinoline. A mechanism for this reaction was proposed.
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Hideo Tani
1959 Volume 7 Issue 8 Pages
930-934
Published: December 20, 1959
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The mechanism of the reaction of 1-alkoxypyridinium compounds with cyanide ion was studied and as the intermediate of this reaction, dihydropyridine-type compounds were confirmed by ultraviolet spectra. Several factors affecting the ratio of the amount of 2- and 4-cyanopyridines in the reaction products were also investigated.
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Tohru Ueda, Eiko Ohtsuka
1959 Volume 7 Issue 8 Pages
935-937
Published: December 20, 1959
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Guanosine diphosphate mannose (GDPM), coenzyme of mannose polymerization, was chemically synthesized. GMP and cyclohexylamine were condensed to form N-cyclohexylphosphoramidate in the presence of DCC. The amidate (III) was reacted with benzyl hydrogen phosphate and after hydrogenation led to GDP (V). (III) and α-d-mannos-1-yl phosphate were condensed in pyridine and, after isolation and purification by ion-exchange chromatography, 83.5% pure GDPM was obtained in 32% yield. The synthetic GDPM was quite identical with the natural one in all respects.
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Hiroshi Igeta
1959 Volume 7 Issue 8 Pages
938-941
Published: December 20, 1959
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Reaction of 3-methoxypyridazine with hydrogen peroxide in glacial acetic acid afforded a mono-N-oxide compound (I). On being treated with phosphoryl chloride, (I) yielded 3-methoxy-6-chloropyridazine (II), whose identification by admixture with an authentic specimen proved (I) to be the 1-oxide (Ia). (I) was hydrolyzed to 3-hydroxy-pyridazien 1-oxide (V). Methylation of (V) afforded the original base (I) as the main product and the reaction of (V) with acetic anhydride yielded maleic acid hydrazide (VI). From the consideration of ultraviolet spectrum and pKa values, it was concluded that the phenolic structure (Vc) has a larger contribution than the tautomeric pyridazone N-oxide structure (Vd).
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Ken'ichi Takeda, Tameto Okanishi, Arimasa Shimaoka
1959 Volume 7 Issue 8 Pages
942-944
Published: December 20, 1959
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Partial synthesis of 25D, 5β-spirostane-2α, 3α-diol, the only unknown isomer of 25D, 5β-spirostane-2, 3-diols, is described.
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Hiroshi Tanida
1959 Volume 7 Issue 8 Pages
944-945
Published: December 20, 1959
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2- and 4-(N-Methylanilino) quinolines were obtained by teh reaction between quinoline 1-oxide and tosyl chloride in N-methylformanilide. In this reaction boric trifluoride was also used as a catalytic agent.
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Masanobu Terasaka
1959 Volume 7 Issue 8 Pages
946-949
Published: December 20, 1959
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1959 Volume 7 Issue 8 Pages
949-951
Published: December 20, 1959
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