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Hikokichi Oura, Tokuko Makino
1958 Volume 6 Issue 5 Pages
451-455
Published: October 15, 1958
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Methylation of methyl 2-hexadecyl-3-hydroxyeicosanate and methyl 2-tetracosyl-3-hydroxyoctacosanate was examined. 2-Tetracosyl-3-methoxyoctacosanoic acid was obtained from this reaction followed by chlorination of its product, but not 2-hexadecyl-3-methoxyeicosanoic acid.
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Hikokichi Oura
1958 Volume 6 Issue 5 Pages
456-462
Published: October 15, 1958
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Condensation of 2-tetracosyl-3-acetoxyoctacosanoic acid chloride and ethyl benzyl tetracosylmalonate afforded ethyl 2, 4-ditetracosyl-3-oxo-5-acetoxytriacontanoate whose reduction with sodium borohydride gave 2, 4-ditetracosyl-3, 5-dihydroxytriacontanoic acid. Preparation of their derivatives was examined.
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Hikokichi Oura
1958 Volume 6 Issue 5 Pages
462-467
Published: October 15, 1958
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Condensation of 2-hexacosyl-3-acetoxytriacontanoic acid chloride and ethyl benzyl tetracosylmalonate gave ethyl 2-tetracosyl-3-oxo-4-hexacosyl-5-acetoxydotriacontanoate whose reduction with sodium borohydride finally afforded the objective 2-tetracosyl-3, 5-dihydroxy-4-hexacosyldotriacontanoic acid, C
82H
164O
4.
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Tetsuji Kametani, Keiichiro Fukumoto, Yukio Nomura
1958 Volume 6 Issue 5 Pages
467-472
Published: October 15, 1958
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The methyl derivatives of 2-, 3-, and 4-methylpyridine, 2-methylthiophene, and 2-methylfuran were synthesized from the corresponding primary alcohol by way of its phenylurethan by treating the alcohol with phenyl isocyanate and catalytic hydrogenation of the urethan formed, in the presence of palladium-black and sodium hydroxide.
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Keizo Kitahonoki
1958 Volume 6 Issue 5 Pages
472-476
Published: October 15, 1958
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The ketol (II'), obtained by ozonolysis of dimethyl agathenedicarboxylate, was converted to the pyridine derivative (III), which was reduced with sodium and ethanol to several stereoisomeric imino-esters (IVa) and imino-alcohols (Va). One of the imino-esters was obtained directly by catalytic reduction of the ketol (II') in methanolic ammonia.
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Shigeo Senda, Akio Suzui
1958 Volume 6 Issue 5 Pages
476-479
Published: October 15, 1958
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All of the compounds derived from the condensation of monosubstituted ureas (substituents : phenyl, cyclohexyl, methyl) and ethyl acetoacetate were 3-substituted 6-methyluracil derivatives. In the case of phenylurea, the hydrolysis of the condensation product gave 1-[3-(3-phenylureido) crotonoyl]-3-phenylurea without the formation of a uracil ring, and when the condensation product was methylated, the ring closure occurred to afford 1, 6-dimethyl-3-phenyluracil. In the case of cyclohexylurea or methylurea, 5-alkyl-6-methyluracil was obtained in a good yield via ethyl 3-(3-alkylureido) crotonate.
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Shigeo Senda, Akio Suzui
1958 Volume 6 Issue 5 Pages
479-482
Published: October 15, 1958
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The methylation of 6-methyl-2-thiouracil with dimethyl sulfate gave 3, 6-dimethyl-and 1, 6-dimethyl-2-methylthio-4-pyrimidone. The alkylation of 6-methyl-2-methylthio-4-pyrimidone with alkyl halide, however, gave both 3-alkyl-6-methyl-2-methylthio-4-pyrimidone and 4-alkoxy-6-methyl-2-methylthiopyrimidine. The compounds obtained above were hydrolyzed to afford 3-alkyl-6-methyluracils and 6-methyluracil. 4-Alkoxy-6-methyl-2-methylthiopyrimidine was also synthesized from 4-chloro-6-methyl-2-methylthiopyrimidine and sodium alkoxide.
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Shigeo Senda, Akio Suzui, Makoto Honda, Hajime Fujimura
1958 Volume 6 Issue 5 Pages
482-487
Published: October 15, 1958
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5-(2-Dimethylaminoacylamino)-1, 3, 6-trialkyluracils, which are analogous to Aminopropylon in chemical structure, were synthesized and their pharmacological activities were tested (Table I). Quaternary ammonium salt of these compounds with methyl bromide showed remarkable increase in their toxicity, but, generally, they showed comparatively satisfactory results both in analgesic activity and toxicity.
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Shigeo Senda, Akio Suzui, Makoto Honda
1958 Volume 6 Issue 5 Pages
487-490
Published: October 15, 1958
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5-Dialkylamino-1, 3, 6-trialkyluracils, which were analogous with aminopyrine in chemical structure, were synthesized systematically and their phamacological actions were investigated. It is interesting that 5-dimethylamino-3-cyclohexyl-1, 6-dimethyluracil (V) showed analgesic, hypothermic, antifebrile, and moreover tranquilizing actions with less toxicity than aminopyrine.
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Shigeo Senda, Makoto Honda, Kyoji Maeno, Hajime Fujimura
1958 Volume 6 Issue 5 Pages
490-495
Published: October 15, 1958
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Various kinds of 5, 6-dialkyl-2-thiouracils, 5, 6-dialkyluracils, and 3, 5, 6-trialkyluracils (alkyl : CH
3, C
2H
5, C
3H
7, C
4H
9, iso-C
4H
9, C
5H
11, iso-C
5H
11), which were analogous with barbital in their chemical structures, were synthesized systematically, and relationship between pharmacological action and chemical structure was investigated. The compounds of this series showed sedative rather than analgesic action, and 3, 6, 5-trialkyluracils (R
3, R
5 : C
4H
9, R
6 : CH
3) showed a comparatively strong sedative action.
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Eiji Ochiai, Takenari Nakagome
1958 Volume 6 Issue 5 Pages
495-496
Published: October 15, 1958
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5-Nitroisochinolin-N-oxyd ergibt beim Behandeln mit Tosylchlorid nach Schotten-Baumann 4-Tosyloxy-5-nitroisochinolin und 5-Nitroisocarbostyril mit der Ausbeute von 50∼60% und 15∼40% bzw. der Theorie. 4-Tosyloxy-5-aminoisochinolin und 4-Hydroxy-5-nitroisochinolin wurden hergestellt.
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Eiji Ochiai, Takenari Nakagome
1958 Volume 6 Issue 5 Pages
497-500
Published: October 15, 1958
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Die Nitrierung von 1, 2, 3, 4-Tetrahydroisochinolin (I) und seinem 2-Methyl-bzw. 2-Acetylderivate (II bzw. III) wurde unter milder Bedingung untersucht. (I) und (II) ergaben dabei ausser dem 7-Nitroderivat, dem Hauptprodukt, noch eine kleine Menge 6-Nitroderivat. Aus (III) konnte man ausser dem 7-Nitroderivat nur ein Mononitroderivat des 2-Acetyl-1-oxo-tetrahydroisochinolins rein isolieren.
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Yosio Sakurai, Hiroshi Imamura, Ayako Moriwaki
1958 Volume 6 Issue 5 Pages
501-504
Published: October 15, 1958
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The fact was presented in this paper that there was no quantitative parallelism between the tumor-growth retarding effect of a compound on animal tumors and its inhibiting effect on dehydrogenase activity in vitro of the living cells of the same kind of tumor. An attention should therefore be paid to this fact when a drug is to be selected for clinical purpose from the anti-cancer agents by comparing their inhibiting activity on this enzyme of tumor piece taken from a patient.
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Masao Uchibayashi
1958 Volume 6 Issue 5 Pages
504-507
Published: October 15, 1958
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Gitorin was obtained efficiently from the leaves of Digitalis lanata in 0.0123% yield by the method combining column chromatography and solvent-partition method, and its structure was confirmed by the Mannich hydrolysis, which furnished gitoxigenin, dianhydrogitoxigenin, and glucose.
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Hayao Nawa, Masao Uchibayashi
1958 Volume 6 Issue 5 Pages
508-511
Published: October 15, 1958
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Rhodexin-B, a cardiac glycoside of Rhodea japonica ROTH., was subjected to the Mannich hydrolysis and oleandrigenin (16-acetylgitoxigenin) was obtained as the main product, together with gitoxigenin, dianhydrogitoxigenin, and rhamnose. From these results the existing formulation for the structure of rhodexin-B and-C were corrected to 16-acetylgitoxigenin rhamnoside (II) and 16-acetylgitoxigenin rhamnosido-glucoside (III), respectively. This report constitutes the first example of the Mannich hydrolysis of the glycosides of oleandrigenin linking with a 2-hydroxy sugar.
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Mitiiti Fujita, Tsutomu Furuya
1958 Volume 6 Issue 5 Pages
511-517
Published: October 15, 1958
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The paper chromatography of more than 30 kinds of natural and synthetic coumarin derivatives was studied using 8 different solvent systems. The relationship between Rf values and structure of compounds in regard to the properties of the developing solvent systems was discussed. The separation of coumarin derivatives by multibuffered chromatography was also studied.
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Mitiiti Fujita, Tsutomu Furuya
1958 Volume 6 Issue 5 Pages
517-520
Published: October 15, 1958
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The metabolic fate of umbelliferone was studied by the quantitative analysis of urinary excrete of rabbits. The orally administered umbelliferone was converted into glucuronide (44.32%) and ethereal sulfate (19.10%) accompanying unchanged umbelliferone (20.23%). An extractor of high efficiency was designed to be employed for the continuous extraction of urinary metabolites.
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Mitiiti Fujita, Tsutomu Furuya
1958 Volume 6 Issue 5 Pages
520-523
Published: October 15, 1958
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The fate of herniarin in the rabbit was studied. The chief metabolite is umbelliferone but a small amount of unchanged herniarin was excreted, and both metabolites were estimated quantitatively. No evidences for biological hydroxylation or lactone-ring cleavage was obtained.
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Toru Masuda, Toyokazu Kishi, Mitsuko Asai, Satoru Kuwada
1958 Volume 6 Issue 5 Pages
523-527
Published: October 15, 1958
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When Er. ashbyii was cultivated, pyruvic acid (V) was detected in the mycelium as well as in the broth. Addition of (V) in the cultivation medium, however, checked the formation of riboflavin (IV) and increased the production of 6-methyl-7-hydroxyribolumazine (VI). Formation of (VI) seems to be due to the reaction of (V) with 4-ribitylamino-5-aminouracil which is assumed to be an intermediate of (IV). Er. ashbyii was cultivated in the basic medium, and determination was conducted on the (IV), (VI), and 6, 7-dimethylribolumazine (III) in the samples collected at regular intervals. As a result, it was found that (III) was produced in a very small quantity, compared with (IV), and (VI) in a rather large quantity. This result is well explained by assuming that (IV) is formed through (III), and (VI) is a final product in this metabolism.
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Shigeru Yoshida, Rinji Takasaki
1958 Volume 6 Issue 5 Pages
527-531
Published: October 15, 1958
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1) Acetylation of perhydrofurothiothiamine (II) and thiothiamine (III) with acid anhydride respectively gave N-acylated perhydrofurothiothiamine (IV) and N, O-diacylated thiothiamine (V). Treatment of N, O-diacetylthiothiamine with acetic anhydride in pyridine afforded N, N, O-triacetylthiothiamine (VI). Alkali treatment of (V) gave N-acylated thiothiamines. 2) Attempts to obtain lipoic anhydride, for the synthesis of N-lipoylthiothiamine, were without avail.
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Kenichi Takeda, Tameto Okanishi, Ariyoshi Shimaoka
1958 Volume 6 Issue 5 Pages
532-536
Published: October 15, 1958
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Two new sapogenins, yonogenin and kogagenin, and tokorogenin were isolated from the epigeous part of Dioscorea Tokoro MAKINO. The structure of yonogenin was established to be 25D, 5β-spirostane-2β, 3α-diol (Va) by its degradation to samogenic acid (IIa) and by its conversion via Δ
2-olefin (III) to samogenin (IVa), which was epimerized to original yonogenin (episamogenin). 25D, 5β-Spirostane-2α, 3β-diol (VIIa) was also prepared.
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Kenichi Takeda, Tokuo Kubota
1958 Volume 6 Issue 5 Pages
536-539
Published: October 15, 1958
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α-Spinasterol had been isolated previously from the root of Bupleurum falcatum L. Its more-soluble sterol fractions were investigated by fractional crystallization and chromatography on alumina. Besides α-spinasterol three sterols, Δ
7-stigmastenol, Δ
22-stigmastenol, and stigmasterol, were isolated and identified. Although Δ
22-Stigmastenol was already known as synthetic material, this work is the first example of its isolation from plants.
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Shoshiro Nakamura
1958 Volume 6 Issue 5 Pages
539-543
Published: October 15, 1958
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Griseolutein-B and-A were purified by the counter-current distribution method and their properties were examined. Diacetylgriseolutein-B was easily purified and crystallized. It had one methoxyl group, two acetyl groups, and one carboxyl group, but no C-methyl group or N-oxide group. Its methyl ester was obtained. Alkaline hydrolysis of diacetylgriseolutein-B gave griseoluteic acid which was crystallized as its methyl ester or as monomethyl ester of monoacetylgriseoluteic acid. Distillation of griseoluteic acid with zinc dust gave phenazine, 1-methoxyphenazine, and another compound. This compound was identified as 1-methoxy-4-methylphenazine by comparison with the synthesized sample. 1-methoxy-4-methylphenazine was synthesized from aniline and 3-nitro-4-methoxytoluene and its two crystal forms were observed.
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Shoshiro Nakamura
1958 Volume 6 Issue 5 Pages
543-547
Published: October 15, 1958
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Decarboxylation of diacetylgriseolutein-B in qinoline with copper gave 1-methoxy-4-hydroxymethylphenazine. The periodic acid oxidation of griseolutein-B gave griseoluteic acid, formic acid, and formaldehyde. From these results a partial structure of griseolutein-B was presented. The reduction of 1-acetoxy-4-methoxycarbonylphenazine with lithium aluminum hydride which gave 1-hydroxy-4-hydroxymethylphenazine and 1-hydroxy-4-methylphenazine was described.
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Shoshiro Nakamura
1958 Volume 6 Issue 5 Pages
547-550
Published: October 15, 1958
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A drastic reduction of diacetylgriseolutein-B monomethyl ester gave 1-methoxy-4, 9-dimethylphenazine. Griseoluteic acid was assumed to be 1-methoxy-4-hydroxymethyl-9-carboxyphenazine. From these results and the periodate oxidation, griseolutein-B was concluded to be 1-methoxy-4-[(1, 2-dihydroxyethoxy) methyl]-9-carboxyphenazine. The synthesis of 1-methoxy-4, 6-dimethylphenazine and 1-methoxy-4, 9-dimethylphenazine is described.
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Tsukasa Kuraishi
1958 Volume 6 Issue 5 Pages
551-556
Published: October 15, 1958
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Infrared and ultraviolet absorption spectra of 4-and 5-carboxy-6-chloro-3-pyridazinol (I and II) and of their esters (IE and IIE) were measured. It was found that (I) exists in a chelated form in its crystalline state and that (II) forms an intermolecular hydrogen bonding. Metal chelate compounds of (I) with nickel, copper, or manganese were reported. The preparation and ultraviolet absorption spectrum of 5-carbamoyl-6-chloro-3-pyridazinol (II
Amide) were described.
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Yoshinori Kidani
1958 Volume 6 Issue 5 Pages
556-562
Published: October 15, 1958
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The properties of copper chelate compound of 1-hydroxyphenazine, which possesses one oxine-like functional group to form a chelate, as well as the composition of the chelate in solution and its dissociation constant were studied by the spectrophotometric method. 1-Hydroxyphenazine-copper chelate forms a five-membered ring compound in a neutral medium. 1-Hydroxyphenazine di-N-oxide also has a chelating functional group which seems to be a little different from the former compound, and the properties and composition of copper chelate were also investigated. The copper chelate of its di-N-oxide forms a six-membered chelate ring.
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Yoshinori Kidani
1958 Volume 6 Issue 5 Pages
563-566
Published: October 15, 1958
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Copper chelates of 1, 6-dihydroxyphenazine and its di-N-oxide, which possess two functional groups, were examined by spectrophotometric method concerning their properties and compositions in solution, as well as their dissociation constants. 1, 6-Dihydroxyphenazine forms a five-membered chelate ring, indicating the molar ratio of 1 : 1, a normal complex. The N-oxide derivative also form a chelate with molar ratio of 1 : 1, forming a six-membered chelate ring.
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Hirotaka Otomasu, Shoichi Nakajima
1958 Volume 6 Issue 5 Pages
566-570
Published: October 15, 1958
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Quinoxaline, quinoxaline N-oxide, and 2, 3-dimethylquinoxaline were resistant to nitration, but the quinoxaline derivatives containing polar functions, either in benzene or pyrazine ring, were readily nitrated. Thus, 5-methoxy-, 6-methoxy-, and 2-hydroxy-3-methyl-quinoxalines yielded upon nitration 5-methoxy-6, 8-dinitro-, 5-nitro-6-methoxy-and 2-hydroxy-3-methyl-6-nitro-quinoxalines, respectively.
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Hisashi Nogami, Fujio Nakagawa
1958 Volume 6 Issue 5 Pages
571-574
Published: October 15, 1958
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Considerations on the colorimetric determination with dye as a weak acid-weak base reaction have been described. Other applications in the pharmaceutical fields are suggested. Several equations were derived on which are based the following five items : 1) Some of organic acids may be determined by colorimetry with a basic dye as well as with organic bases. 2) The dye which combined with sample reaches maximum value at a certain pH value. 3) Dissociation constants of a sample and of a dye should preferably be as large as possible. 4) The calibration curve is linear. 5) In general, the ratio of combination of a sample and a dye is nearly in integral ratio, such as 1 : 1.
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Yoshio Ban, Takeshi Oishi
1958 Volume 6 Issue 5 Pages
574-576
Published: October 15, 1958
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3, 4-Dimethoxyphenethyl alcohol and 3, 4-methylenedioxyphenethyl alcohol were respectively prepared from veraltraldehyde and piperonal in a four-step process involving Darzens reaction with the over-all yield of 45∼50%.
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Shigeru Yoshida, Mitsuru Kataoka
1958 Volume 6 Issue 5 Pages
576-577
Published: October 15, 1958
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N-Acyl-O, S-dibenzoylthiamines (II) were prepared by the application of acid anhydride to O, S-dibenzoylthiamine (I).
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Kyozo Hayashi
1958 Volume 6 Issue 5 Pages
578a
Published: October 15, 1958
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Tsunematsu Takemoto, Koji Daigo
1958 Volume 6 Issue 5 Pages
578b-580
Published: October 15, 1958
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Kyosuke Tsuda, Ryoichi Hayatsu
1958 Volume 6 Issue 5 Pages
580-582
Published: October 15, 1958
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