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Eiji Ochiai, Chikara Kaneko
1959 Volume 7 Issue 3 Pages
267-273
Published: May 10, 1959
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Die Nitrierung von Chinolin-1-oxyd mittels Benzoylnitrat wurde in der Weise verbessert und vereinfacht, dass man auf Chinolin-1-oxyd in Chloroform-Losung zuerst Benzoylchlorid und dann Silbernitrat einwirken lasst. Beim analogen Behandeln von Chinolin-1-oxyd mit Acetylchlorid und Silbernitrat konnte man ausser dem 3-und 3, 6-Dinitroderivat eine kleine Menge 6-Nitrochinolin-1-oxyd aber kein 1-Acetoxy-3, 6-dinitrocarbostyril isolieren. Das letztere konnte man jedoch beim Einwirken der uberschussigen Reagenzien auf 3-Nitrochinolin-1-oxyd erhalten. 3, 6-Dinitrochinolin-1-oxyd ergab bei der Einwirkung von Benzoylnitrat 1-Benzoyloxy-3, 6-dinitrocarbostyril. Ein umgestalteter Mechanismus fur die Reaktion wurde vorgeschlagen.
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Chikara Kaneko
1959 Volume 7 Issue 3 Pages
273-277
Published: May 10, 1959
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Bei der Chlorierung von 2-Hydroxychinolin-1-oxyd mit Phosphoroxychlorid wurde 2, 4-Dichlorchinolin erhalten. 2-Hydroxychinolin-1-oxyd ergab beim Nitrieren mit Salpetersaure in Eisessig-Losung das 6, 8-Dinitroderivat. Das Acetyl-, Benzoyl-und Tosylderivate von 2-Hydroxychinolin-1-oxyd und seiner 6, 8-und 3, 6-Dinitroderivate wurden hergestellt. Ihre Konstitutionen wurden durch die IR-spektrographische Untersuchung als die 1-Acyloxycarbostyril-Derivate festgestellt. 1-Benzoyloxycarbostyril widersteht der Einwirkung von Benzoylnitrat, wahrend Carbostyril dabei 6-Nitroderivat ergibt. Die katalytische Reduktion des Tosylates von 2-Hydroxychinolin-1-oxyd mit Palladium-Kohle in Athanol-Losung ergab 3, 4-Dihydrocarbostyril.
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Shichiro Akiya, Toshiaki Osawa
1959 Volume 7 Issue 3 Pages
277-281
Published: May 10, 1959
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Methyl 4, 6-benzylidene-β-D-glucosaminide hydrochloride (III) was synthesized by a new method. Deamination of (III) with sodium nitrite in weak acetic acidity resulted in facile cleavage of glycosidic bond and simultaneous dehydration between C-2 and C-5 positions to form 2, 5-anhydro-4, 6-benzylidene-D-mannose. On the other hand, deamination of methyl 2-amino-4, 6-benzylidene-2-desoxy-α-D-altroside hydrochloride (V) with sodium nitrite afforded methyl 2, 3-anhydro-4, 6-benzylidene-α-D-alloside (VI) without any change in glycosidic bond. The mechanisms of these deamination reactions were discussed.
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Zen-ichi Horii, Yasumitsu Tamura, Kunihiko Tanaka, Takefumi Momose
1959 Volume 7 Issue 3 Pages
281-286
Published: May 10, 1959
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Terranaphthoic acid, a degradation product of oxytetracycline, was synthesized and the structure proposed by Hochstein, et al. for this compound was thereby confirmed.
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Hikokichi Oura
1959 Volume 7 Issue 3 Pages
286-290
Published: May 10, 1959
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The α-compound, m.p. 92∼93.5°, and β-compound, m.p. 87∼89°, of 2-tetracosyl-3-hydroxyoctacosanoic acid was deuterated and their infrared spectra were measured. Attempt was made to elucidate the steric configuration of α-and β-compounds from difference in the strength of hydrogen bonds but there was no marked difference between the two isomers. Some difference, however, was found to exist between the α-and β-compounds in the velocity of deuteration.
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Morizo Ishidate, Toyokazu Kishi, Shoji Takitani
1959 Volume 7 Issue 3 Pages
291-293_1
Published: May 10, 1959
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In connection with the known fact that some aromatic amines are metabolized and excreted in urine as glucuronic acid conjugates, the N-glucosyluronates of primary aromatic amines, such as aniline, toluidine, p-chloroaniline, p-aminoazobenzene, p-dimethyl-aminoaniline, and p-phenylenediamine, were prepared. The same compound of secondary amines were not obtained. It was established that the conjugate should have a structure of N-glucopyranosyluronic acid, possibly in β-configuration, from the fact the acetylation product derived from methyl ester of glucuronic acid conjugate of aniline was identical with the compound prepared from methyl (2, 3, 4-tri-O-acetylglucopyranosyl-bromid) uronate and aniline.
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Jun Okuda
1959 Volume 7 Issue 3 Pages
295-296
Published: May 10, 1959
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Distribution of FMN-dephosphorylating enzyme in the cells of the small intestine was studied. 1) In the case of a homogenate, the highest activity was found in the jejunum. The activity of the ileum was lower than that of the duodenum. 2) In the case of subcellular fraction, about 80% of the activity was found in the cytoplasm fraction. In each case, the highest activity was found in the cytoplasm fraction and that in the mitochondria fraction was higher than that of the nucleus fraction.
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Hiroshi Yamanaka
1959 Volume 7 Issue 3 Pages
297-299
Published: May 10, 1959
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4-Methoxypyrimidine 1-oxide was prepared and its Reissert reaction afforded 4-methoxypyrimidine-2-carbonitrile, which was derived to 2, 4-dimethoxypyrimidine to confirm the structure. At the same time, difference in the nucleophilic activity of the 2-and 4-positions in pyrimidine 1-oxide was clarified. During the course of this work, a simple process for the preparation of 4-methoxypyrimidine was established.
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Manabu Hanano
1959 Volume 7 Issue 3 Pages
300-305
Published: May 10, 1959
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1) A diffusion model was presented on the percutaneous absorption from lipidinsoluble vehicle and the equation was derived in regard to the decrease in the rate of concentration of a drug applied : C/C
0=exp (-At/RV) where C
0 is the initial concentration of a drug, C the concentration at time t, R the over-all resistance, V the volume of vehicle, and A the area applied. The relation between the rate of decrease and the degree of dissociation of a drug was also expressed from the same model : C/C
0=exp (-At (1-a)/RV) where a is the degree of dissociation. 2) Both equations were proved to be conformable to the absorption of salicylic and benzoic acids from the aqueous and buffer solutions through the intact human skin.
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Michiko Kagawa
1959 Volume 7 Issue 3 Pages
306-315
Published: May 10, 1959
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1. 4-Acetylborneol was synthesized by an indirect process and it was cofirmed that the Hurd-Christ's 2-acetyl-6-hydroxycamphane is 4-acetylborneol and one kind of Rupe reaction occurs in this case. 2. By heating 2-ethynylborneol with dilute hydrochloric acid, 2-camphanylidene-acetaldehyde was obtained, no unsaturated ketone having been found, which is a product of Rupe reaction. Therefore the Meyer-Schuster rearrangement occurs in this case. 3. 2-Camphanylideneacetaldehyde was obtained by standing 2-ethynylborneol with conc. formic acid at 40°, showing that it undergoes Meyer-Schuster rearrangement at 40°and Rupe reaction at high temperature. 4. 4-Acetylborneol, 2-ethynylcamphene, 2-acetylcamphene, 2-acetylborneol, 4-ethynylcamphene, 4-acetylcamphene, 4-acetylcamphor, 4-ethynylborneol, and 4-ethynylcamphor, presumed to be related with anionotropic rearrangement of 2-ethynylborneol, were synthesized and their properties were studied.
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Hiroya Tanabe
1959 Volume 7 Issue 3 Pages
316-319
Published: May 10, 1959
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Methyl methacrylate polymerised in a concentration of about 10
-3M in the reaction system of aniline oxidized with periodic acid, and benzoic acid was oxidized in a concentration of 10
-2M to salicylic acid in the same system. From these facts it was proved that the oxidation of aniline is a radical reaction and a free hydroxyl radical is produced, thereby proving the correctness of presumptions reported in the previous paper of this series.
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Itiro Yosioka, Shintaro Takahashi, Hiroshi Hikino, Yasuko Sasaki
1959 Volume 7 Issue 3 Pages
319-323
Published: May 10, 1959
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The sesquiterpenoid alcohol, the so-called atractylol, a major constituent of the essential oil from the rhizomes of Atractylodes lancea DE CANDOLLE (Compositae), was separated into the known eudesmol and a new sesquiterpenoid alcohol, hinesol, which were characterised. Association of the two alcohols was established unambiguously by the regeneration of the so-called atractylol from them.
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Sadao Iguchi, Kazuhito Hisatsune, Michiko Himeno, Shigeteru Muraoka
1959 Volume 7 Issue 3 Pages
323-328
Published: May 10, 1959
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Yoshinobu Sato, Takuzo Nishimura
1959 Volume 7 Issue 3 Pages
329-331
Published: May 10, 1959
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4-Cyano-5-methoxymethylquinoline was prepared from quinoline-5-carboxylic acid through several steps. This quinoline compound was found to easily form a δ-lactone compound on boiling with conc. hydrochloric acid.
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Hisashi Nogami, Jun Hasegawa, Yoshinobu Nakai
1959 Volume 7 Issue 3 Pages
331-337
Published: May 10, 1959
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A new mothod for examining the disintegration of a tablet and a granule continuously and in detail was proposed. The beginning of disintegration, the time necessary for the maximum surface area of tablet ingredient, and the time required for a powder to dissolve completely were determined precisely. This method was applied to the tablet of calcium carbonate in the acetate buffer of pH 4.2 and the following conclusions were drawn. a) The tablet prepared from CaCO
3 powder by direct compression disintegrated and dissolved very rapidly, and difference between the original powder and the tablet was not recognized. b) The disintegration and solution rate of CaCO
3 granule that contained starch paste was not rapid and larger particles remained undissolved in the final stage. c) It was evidenced that the tablet prepared from CaCO
3 granule disintegreted more slowly than the tablet prepared by direct compression.
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Hisashi Nogami, Jun Hasegawa, Yoshinobu Nakai
1959 Volume 7 Issue 3 Pages
337-342
Published: May 10, 1959
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Disintegration of a granule and the tablet of basic magnesium carbonate was investigated, apparent particle-size distribution was compared, and the effects of binder and disintegrator was studied by thermal analysis. The relation between testing method for disintegration by U.S.P. and J.P., and the change of surface area was discussed, and the following conclusions were drawn. 1) Judging from the change of surface area, the effect of compressional force was not notable in a tablet prepared with well-disintegrating granule. 2) The disintegration time of a tablet prepared by direct compression was very prolonged and this relation was clearly recognized by the evaluation of apparent particle-size distribution of a tablet.
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Tatsuo Yamauchi
1959 Volume 7 Issue 3 Pages
343-348
Published: May 10, 1959
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1) 25D-Spirosta-3, 5-diene (I), cholesta-3, 5-diene, and solanida-3, 5-diene were found to be photometrically assayed on a micro-scale and accurately using a characteristic extinction at 235mμ due to 3, 5-diene system in the molecules. With the aid of this method, the yields of (I), the main by-product accompanying diosgenin, from diosgenin and its glycosides upon acid treatment under various conditions were determined in order to find the optimal hydrolytic condition of diosgenin glycosides to minimize the yield of (I). 2) In comparison with diosgenin and its glycosides, the formation of corresponding ⊿
3, 5-steroid by acid treatment from epi-diosgenin, 25D-spirost-4-en-3-ol, cholesterol, cholesterol glucoside, epi-cholesterol, solanidine, and solanine was examined in the same way. 3) A minor amount of 3-chloro-25D-spirost-5-ene was obtained besides (I) on boiling diosgenin with 2∼4N hydrochloric acid in 50% ethanol.
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Haruo Saikachi, Takuzo Hisano
1959 Volume 7 Issue 3 Pages
349-356
Published: May 10, 1959
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The condensation of 2-picoline with various aromatic primary amines (or nitro compounds) in the presence of sulfur was carried out at elevated temperature. This reaction was tentatively divided into three types : The first type is a simple thiopicolinoyl ; the second, a mixed type, yielding thiopicolinoyl and thiazolyl cyclization products ; and the last, unchanged (or resinous). It is noteworthy that protomeric amino group, such as that of N
1-position of sulfanilamide and 2-position of pyridine, was active to some extent for this reaction. Oxidative cyclization of five thiopicolinoyl intermediates (XXI, XXIII, and XXIV) from dianisidine, sulfanilamide, homosulfanilamide, 2-aminopyridine, and 5-nitro-2-aminopyridine with potassium ferricyanide was unsuccessful, but not for (XXII) and (XXV). The chemical structure of these cyclization products was discussed on the basis of their ultraviolet spectral observation and electronic theory. Microbiological activity of these compounds will be reported elsewhere.
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Takeo Ishiguro, Hiroyuki Mogi
1959 Volume 7 Issue 3 Pages
356-358
Published: May 10, 1959
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Nous avons deduit l'existence des hydrates a 1/2, 2, 4, 6, 8, 9, et 10H
2O du diphenylhydantoinate de calcium a la lumiere des resultats de la mesure de la pression de la vapeur d'eau de dissociation des hydrates du diphenylhydantoinate de calcium. Parmices hydrates, l'hydrate a 8 H
2O ou l'hydrate a 6 H
2O sont les plus stables dans l'etat normal et les hydrates a 9 et 10H
2O sont efflorescents.
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Takeo Ishiguro, Hiroyuki Mogi
1959 Volume 7 Issue 3 Pages
359-361
Published: May 10, 1959
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Nous avons obtenu la courbe de solubilite et la courbe de viscosite-temperature, en mesurant la solubilite du diphenylhydantoinate de calcium dans l'eau et la viscosite de la solution saturee a des temperature comprises entre 20°et 60°, et nous avons determine les temperatures de transition des hydrates du diphenylhydantoinate de calcium d'apres le fait que les points de discontinuite dans ces courbes correspondent aux points de transition des parties solides (hydrates de DHC) qui coexistent avec la solution saturee.
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Toru Masuda, Toyokazu Kishi, Mitsuko Asai, Satoru Kuwada
1959 Volume 7 Issue 3 Pages
361-365
Published: May 10, 1959
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Attempt was made for the total synthesis of 6, 7-dimethylribolumazine which is considered to be an intermediate in the biosynthesis of riboflavin. In the first place, crude 4-ribitylaminouracil was prepared from 4-chlorouracil and D-ribamine. Although this compound could not be produced in a pure enough state, it was isolated as its 5-nitroso derivative as pretty rods, m.p. 105°(decomp.). This nitroso compound was reduced to the corresponding amino compound with sodium hydrosulfite, but as the latter could not be separated pure, it was immediately led to 6, 7-dimethylribolumazine by reaction with diacetyl. Physical properties of the product were in complete agreement with those of the 6, 7-dimethylribolumazine separated from the mycelium of Er. ashbyii, and the structure of the product was thereby positively established.
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Toru Masuda, Toyokazu Kishi, Mitsuko Asai, Satoru Kuwada
1959 Volume 7 Issue 3 Pages
366-368
Published: May 10, 1959
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According to the method reported previously 4-ribitylaminouracil was produced from 4-chlorouracil and D-ribamine, and its nitroso derivative was reduced to 4-ribitylamino-5-aminouracil, which was isolated as hydrochloride or sulfite. Reaction of the salt with pyruvic acid in the presence of hydrazine afforded 6-methyl-7-hydroxy-8-D-ribityl-2 (3H), 4 (8H)-pteridinedione, m.p. 263°(decomp.), which was in complete accord in every property with purple fluorescent 6-methyl-7-hydroxyribolumazine isolated from the mycelium of Eremothecium ashbyii.
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Kyosuke Tsuda, Toshinobu Asai, Eiji Ohki, Atsuji Tanaka, Takemasa Mats ...
1959 Volume 7 Issue 3 Pages
369-372
Published: May 10, 1959
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Progesteron (I) wurde durch Fermentierung mit Syncephalastrum racemosum COHN in 7α, 15β-Dihydroxyprogesteron (II) und Trihydroxyprogesteron (III) ubergefuhrt. Das letztere konnte auch durch mikrobiologische Umwandlung von (II) mit gleichem Mikro-organismus erhalten werden. Damit wurden die Stellungen 7α und 15β fur die zwei Hydroxy-Gruppen im Trihydroxylierungsprodukt gesichert. Fur das dritte Hydroxyl wurde die 14α-Stellung vorgeschlagen und diese Zuordnung durch Vergleichung mit Cholestan-14α, 15α-diol bzw. Cholestan-14α, 15β-diol in Bezug auf der Verbrauchsgeschwindigkeit von Perjodsaure bzw. Bleitetraacetat gestutzt.
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Y. Kase, T. Yuizono, T. Yamasaki, T. Yamada, S. Io, M. Tamiya, I. Kond ...
1959 Volume 7 Issue 3 Pages
372-377
Published: May 10, 1959
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1-Methyl-3-di (2-thienyl) methylenepiperidine citrate (AT-327) showed antitussive effect more potent than codeine in unanesthetized dogs and effect approximately equal to codeine in pentobarbitalized cats. The efficacy was also demonstrated in clinical trials with 45 patients. The antitussive activity seemed to be due to its direct action on the cough center per se. The drug did not show any analgesic activity, tendency of establishing tolerance, or indicate addiction liability, either in animal experiments or in clinical trials. The toxicity was found to be lower than that of codeine in the mouse. Other pharmacological properties of the drug were also discussed briefly.
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Yoshitoshi Kase, Tomokazu Yuizono
1959 Volume 7 Issue 3 Pages
378-382
Published: May 10, 1959
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An introduction of a piperidino group into a certain compound can manifest or strengthen antitussive activity, independent of analgesic activity. This property seems to appear not only in analgesics but also in other compounds possessing depressant action on the central nervous system to some extent.
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Tyunosin Ukita, Kinzo Nagasawa
1959 Volume 7 Issue 3 Pages
383-385
Published: May 10, 1959
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Eiji Ochiai, Masayuki Ishikawa
1959 Volume 7 Issue 3 Pages
386-389
Published: May 10, 1959
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Tohru Ueda, Eiko Ohtsuka
1959 Volume 7 Issue 3 Pages
389-390
Published: May 10, 1959
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Morizo Ishidate, Yoshio Sakurai, Yutaka Kuwada
1959 Volume 7 Issue 3 Pages
391-392
Published: May 10, 1959
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Mahiko Horiuchi
1959 Volume 7 Issue 3 Pages
393-394
Published: May 10, 1959
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Issei Iwai, Tetsuo Hiraoka
1959 Volume 7 Issue 3 Pages
394-395
Published: May 10, 1959
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