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Studies on the Syntheses of Coclaurine and Analogous Compounds. (4) Synthesis of dl-Isococlaurine
富田 眞雄, 山口 秀夫
1952 年 72 巻 10 号 p.
1219-1222
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The authors synthesized
dl-compound of the so-called isococlaurine, the structure of which had been presumed by King as 1-(4′-hydroxybenzyl)-6-hydroxy-7-methoxy-1, 2, 3, 4-tetrahydroisoquinoline (II). Hydrochloride, m.p. 215°. Free base, m.p. 135-136°.
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Alkaloids of Cyclea insularis (Makino) Diels. (8). Synthesis of Depsidan Nucleus and the Structure of Insularine
犬伏 康夫
1952 年 72 巻 10 号 p.
1223-1227
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The author synthesized depsidan (V), and by comparison of the ultraviolet absorption curve of the above substance with that of the decarboxylated compound (XV) of insularic acid obtained by the decomposition of insularine, an alkaloid of
Cyclea insularis (Makino) Diels, proved spectrochemically, as well as synthetically, that insularine has the nucleus of depsidan (V) in its molecule.
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小菅 卓夫
1952 年 72 巻 10 号 p.
1227-1231
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
Chemical properties of an antimicrobial substance isolated from
Houttuynia cordata, a popular medicinal plant in eastern and southeastern Asia, were investigated and it was found to contain decanoyl acetaldehyde. Synthesis of the substance was achieved from methyl nonyl ketone and ethyl formate by means of the Claisen condensation. In the course of this work, it was also established that sodium bisulfite adduct of enolizable aldehyde can be prepared by leading sulfur dioxide into the sodium salt solution.
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藤田 栄一, 西条 利明, 富田 眞雄
1952 年 72 巻 10 号 p.
1232-1237
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
M. Tomita and Fujita previously decomposed
O-methyloxyacanthine (II) by means of metallic sodium in liquid ammonia, and obtained two kinds of bisected bases, one of the
d-type (III) and the other
l-type (IV), thus verifying that the configuration of the asymmetric center at the right-hand tetrahydroisoquinoline nucleus in the molecule of (II) underawent inversion from
d-type to
l-type by this reaction.
Moreover, it had already been clarified by Bruchhausen that when oxyacanthine (I) was reacted with 0.5 molar equivalent of hydrochloric acid, the configurations of the two asymmetric centers in its molecule underwent inversion from (+, +) to (+, -), and repandine (V) of its diastereoisomer was formed. In the present series of experiments, the authors carried out the decomposition of
O-methylrepandine (VI) by metallic sodium in liquid ammonia, and proved two kinds of
d-type (VII) and
d-type (IX) as the bisected bases. Thus, it has been revealed that the configuration of the asymmetric center at the right-hand tetrahydroisoquinoline nucleus in (VI) again underwent inversion from
l-type to
d-type by this reaction.
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諸江 辰男, 松島 照海, 宮本 統
1952 年 72 巻 10 号 p.
1238-1240
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
In order to discover an advantageous method of preparing 3, 4-benzotropolone, the Cook's synthetic procedure was reëxamined. This compound was obtained in a good yield from cinnamic aldehyde, via phenylvaleric acid. At the same time, monobromo-benzotropolone was obtained.
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Critical Examination of the Analytical Method of Iron, Copper, Zinc, Cobalt, Nickel, Manganse, and Magnesium in Tissues
木村 健二郎, 原 礼之助, 飯島 登
1952 年 72 巻 10 号 p.
1240-1245
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The methods of analysis are examined in the microdetermination of iron, copper, zinc, cobalt, nickel, manganese, and magnesium in tissues. Following methods have given good results.
1) For serum iron-Colorimetric determination with α, α′-bipyridyl.
2) For iron in organ-Thiocyanate method. Addition of acetone makes the analysis more accurate and sensitive.
3) For copper in serum and organ, and for zinc in organ-Extraction titration with dithizone solution.
4) For cobalt in organ-Colorimetric determination with nitroso-R-salt.
5) For nickel in organ-Colorimetric determination with dimethylglyoxime.
6) For manganese in organ-Colorimetric determination in permanganate with an oxidizing agent, silver peroxide.
7) For magnesium in serum and each tissue-Colorimetric determination with Titan yellow. Colorimetry with oxine is not suitable.
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Metabolism of Iron and Copper
木村 健二郎, 飯島 登, 原 礼之助
1952 年 72 巻 10 号 p.
1245-1249
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
Using a dog as the experimental animal, the authors studied systematically the metabolism of iron and copper from normal to hemorrhagic shock state. By bleeding, the hypotential state continued for several hours, finally the animal fell into a sate of shock. The liver, spleen, and serum were chosen for this study.
1) The iron and copper content of the liver decreased markedly without any exception. No marked decrease of iron takes place during the hypotential state. Only when the state of shock was finally reached was iron liberated from the liver.
2) The serum iron value in vein distinctly decreased without any exception, while, in artery, the decrease was not so marked. In all cases, the serum iron level in artery was always more than that in the vein.
3) The variation of serum copper value was not always consistent. It is assumed that the general tendency is an increase. No difference could be observed in the content of vein serum and that of artery serum.
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Metabolism of Cobalt, Nickel, Zinc, Manganese, and Magnesium
木村 健二郎, 飯島 登, 原 礼之助
1952 年 72 巻 10 号 p.
1249-1252
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
Using a dog as an experimental animal, the metabolism of cobalt, nickel, zinc, manganese, and magnesium has been studied from normal to secondary hemorrhagic shock. The results are as follows:
1) The content of cobalt, nickel, zinc, manganese, and magnesium markedly decreased in the liver.
2) No marked change occured in the spleen.
3) Of vein serum, the magnesium content increased in a state of hemorrhagic shock.
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Change in Ferritin Iron Content
木村 健二郎, 飯島 登, 原 礼之助
1952 年 72 巻 10 号 p.
1252-1253
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The content of ferritin iron was determined in a normal state and in hemorrhagic shock. The results are summarized as follows:
1) Normal ferritin obtained in the present experiments contains about 15-17% iron. These values seem to be slightly smaller compared with those obtained by other workers.
2) Ferritin of hemorrhagic shock shows markedly lower iron content. The nitrogen content remains almost constant independent of whether it is in a normal state or in a hemorrhagic shock.
3) These results show that the liberation of ferritin iron occurs in the hemorrhagic shock.
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Liberation of Ferritin Iron
木村 健二郎, 原 礼之助, 飯島 登
1952 年 72 巻 10 号 p.
1254-1256
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The effect of some inorganic substances, nitrogen, carbon dioxide, and hydrogen gas, and copper, cobalt, nickel, zinc, manganese, tin, and magnesium, were studied in the ferritin-iron liberation. The results are summarized as follows:
1) Hydrogen gas promotes the ferritin-iron liberation. The effect of nitrogen and carbon dioxide gas was not clear.
2) The effect of copper, cobalt, nickel, manganese, zinc, and magnesium salt was not clear, but, in the existence of hydrogen gas, it seems that these salts slightly promote the ferritin-iron liberation.
3) Stannous chloride slightly promotes the ferritin-iron liberation. This may be due to the reducing activities.
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Syntheses of Salicifoline Chloride and Analogous Compounds
富田 眞雄, 中野 立彦
1952 年 72 巻 10 号 p.
1256-1260
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The authors synthesized from isovanillin, salicifoline chloride (I), viz., β-(3-hydroxy-4-methoxyphenyl)-ethyl-trimethylammonium chloride, a main base of
Magnolia salicifolia Maxim.,
Magnolia Kobus DC., and
Magnolia stellata Maxim., belonging to the Magnoliaceae, which grow in Japan. Thus, the structure of salicifoline chloride has synthetically been confirmed as being represented by formula (I). In this connection, β-(3-methoxy-4-hydroxyphenyl)-ethyl-trimethylammonium chloride (IV), β-(2-hydroxy-3-methoxyphenyl)-ethyl-trimethylammonium chloride (VI), and β-(2, 3-dimethoxyphenyl)-ethyl-trimethylammonium iodide (VII), having the structure analogous to that of salicifoline chloride, have also been synthesized.
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Alkaloids of Magnolia denudata Desr. (1)
富田 眞雄, 中野 立彦
1952 年 72 巻 10 号 p.
1260-1262
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The authors isolated and identified three kinds of quaternary bases from the bark of
Magnolia denudata Desr., belonging to the Magnoliaceae, which grows in Japan. The one was isolated as the chloride, crystallizing in colorless prisms, m.p. 260-261° (decomp.), and the other two as the picrates, crystallizing in yellow needles, m.p. 181.5-182°, and in orange yellow prisms, m.p. 222-223°, respectively. As a result of examination, it has been confirmed that the first two bases are salicif oline chloride (I) and magnocurarine (II) picrate, respectively. The last picrate of m.p. 222-223° is now being studied.
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Chlorination of 2-Alkyl-6-Nitro- and 2-Alkylbenzothiazoles
水野 義久, 足立 亀久夫, 神田 進
1952 年 72 巻 10 号 p.
1263-1265
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) Possible routes of preparing benzothiazole analogs of chloramphenicol were examined, one of which was proved to be promising. The route is as follows: 2-Ethyl-, 2-ethyl-6-nitro-, 2-dichloroethyl-6-nitro-, 2-acetyl-6-nitro-(X), and to 2-α-bromoacetyl-6-nitrobenzothiazole. Overall yield of (X) by the present route was found to be 18%.
2) During the present investigation, following new compounds were prepared: Benzothiazolyl-2-carbohydrazide, m.p. 171°; 2-acetylbenzothiazole, m.p. 107-108°, its semicarbazone, m.p. 258° (decomp.); 2-acetyl-6-nitrobenzothiazole, m.p. 191-192°; 2-α, α′-dichloro-6-nitrobenzothiazole, m.p. 93-94°; 2-bromoacetyl-6-nitrobenzothiazole, m.p. 146-147°.
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Nitration of 2-Substituted Benzothiazoles
水野 義久, 足立 亀久夫, 中村 要
1952 年 72 巻 10 号 p.
1266-1268
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) Benzothiazole, 2-methyl-, 2-methoxy-, 2-chloro-, 2-acetyl-, 2-carbethoxy-, and 2-nitrobenzothiazoles were nitrated under comparable condtions. Yield of 2-mononitro derivatives were as follows: 6-Nitro-2-methyl-, 89%, 6-nitro-2-methoxy-, 82% (including that of 2-hydroxy-6-nitrobenzothiazole); 6-nitrobenzothiazole, 62%; 6-nitro-2-chloro-, 48%; 6-nitro-2-acetyl-, 28%. From 2-nitrobenzothiazole, no nitration product was obtained.
2) In benzothiazole, 2 and 6-positions may be in para-relation to each other, at least in an activated state.
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Nitration of 4-Substituted 2-Methylbenzotltiazoles
水野 義久, 足立 亀久夫
1952 年 72 巻 10 号 p.
1269-1271
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) Nitration of 4-substituted 2-methylbenzothiazoles was carried out to examine the behavior of the substituent at 4-position towards nitration. In the nitration, effect of the substituent is predominant, as compared with superposed 6-position-directing power of the benzothiazole nucleus and 2-methyl group on it. The yield ratio of 5-nitro product to that of 7-nitro product is considerably dependent on the nature of the substituent. That is due to the inductive effect of the substituent.
2) The following new compounds were prepared: 2, 4-Dimethyl-7-nitro-, m.p. 155-156°; 2, 4-dimethyl-5-nitro-, m.p. 105-106°; 2-methyl-7-nitro-4-methoxy-, m.p. 183°; and 2-methyl-4-methoxy-5(?)-nitrobenzothiazole, m.p. 103°.
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Nitration of 2-Methylnitrobenzothiazoles
水野 義久, 足立 亀久夫
1952 年 72 巻 10 号 p.
1271-1272
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
On nitration of 4-nitro- and 7-nitro-2-methylbenzothiazoles, dinitro-2-methylbenzothiazoles, presumably 4, 6-dinitro- and 5, 7-dinitro-2-methylbenzothiazolés, were obtained. On the other hand, nitration of 5-nitro- and 6-nitro-2-methylbenzothiazoles failed to give dinitro-2-methylbenzothiazoles.
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On the Relative Stability of Benzoquinolizinium Ring System
菅沢 重彦, 赤星 三彌, 鈴木 眞言
1952 年 72 巻 10 号 p.
1273-1277
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
An attempted selective hydrogenation of 9:10-double bond of 3, 4-dihydro-9, 10-dehydro-(2′, 1′:1, 2-benzoquinolizinium) salts by means of Na
2S
2O
4-Na
2CO
3 ended fruitless. In its stead ring cleavage took place, yielding
N-β-phenethylpyridones with quantitative yield in smooth reaction. This clvaeage reaction appeared to be a base-induced one, since sodium hydroxide or silver oxide worked as well, whereas smooth cleavage was effected by sodium carbonate only in the presence of sodium dithionite, and the labile quinolinium hydrogen sulfite formed first as an intermediate seems to be prerequisite in this case. The selective hydrogenation was achieved with LiAlH
4 in absolute ether. The compound thus produced (VIII) was found to be highly sensitive to oxidation, rapidly decolorizing on exposure to air.
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On the Relative Stability of Dibenzoquinolizinium Ring System
赤星 三彌
1952 年 72 巻 10 号 p.
1277-1281
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
Those dibenzoquinolizinium salts, prepared from β-phenethyl bromides and quinoline or isoquinoline via three stage-reactions, were cleaved rather more easily than the corresponding monoquinolizinium salts by means of Na
2S
2O
4-Na
2CO
3 or sodium hydroxide. Somewhat similarly constructed berberine chloride, however, was reduced selectively by the former reagent, affording dihydro-anhydroberberine. 9:10-Double bond of 4′, 5′-methylenedioxy-3, 4, 5, 6, 7, 8-hexahydro-9, 10-dehydro-(2′, 1′:1, 2-benzoquinolizinium) salt (IX) was also reduced smoothly by this means. The influences of some substituents on the relative stability of benzoquinolizinium ring system were also discussed.
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An Estrogen Bioassay based on the Weight of Mice Uterus, and its Application. (1). Test of the Validity of this Method as Qualitative and Quantitative Assay
伊藤 四十二, 玉置 文一, 江草 雅子, 坂本 秀治
1952 年 72 巻 10 号 p.
1282-1286
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) By the bioassay, based on the uterine weight of mice, the estrogen which is at least more potential than 0.6 microgram of estrone can be clearly certified.
2) The sum of responses, caused by several dosages of estrone, could not be certified as being maximum at 72nd hour after injection, even after the reduction of covariance between body weight and uterine weight. Without reduction, the effect due to the difference of dosage could be certificed as being significant.
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Estrogen Biossay, based on the Weight of Mice Uterus, and its Application (2). Further Investigation on the Experimental Data and Test of the Lineality of log Dose-Response Curves
Yosoji Ito, Bun-ichi Tamaoki, Masasko Egusa, Hideharu Sakamoto
1952 年 72 巻 10 号 p.
1286-1290
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) After further analysis of Experiment II, the response at the 72nd hour after injection was certified as being most suitable for parallel line assay among the responses at every 24 hours, in respect to the lineality of its log dose-response curve and the quantity of its “λ”,
2) The relationship between the reduced responses and the log doses could be found as being linear in Experiment II.
3) The unreduced responses caused by estrone and estradiol at the 72nd hour after injection, were certified as being proportional to their log doses.
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Estrogen Bioassay, based on the Weight of Mice Uterus, and its Application. (3) The Application of this Method for Qualitative and Quantitative Assay
Yosoji Ito, Bun-ichi Tamaoki, Masako Egusa, Hideharu Sakamoto
1952 年 72 巻 10 号 p.
1290-1294
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The bioassay, based on the uterine weight of mice, was applied as a qualitative assay to test the estrogenic activities of the extracts from whale ovaries, whale testis, and hog testis, and it was found in this assay that only the extract from whale ovaries possessed a significant estrogenic activity, while the others had not. The estrogenic activities of several synthetic estrogens were quantitatively assayed, using the 4-point assay design, to calculate their relative potencies, which were tabulated.
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Effect of Pterins on the Yoshida Sarcoma
櫻井 欽夫, 吉野 兄史
1952 年 72 巻 10 号 p.
1294-1296
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
Aminopterin and other simpler derivatives of 2, 4-diamino-4-hydroxy- or 2-amino-4-hydroxy-pteridine were synthesized and their effect upon Yoshida ascite sarcoma was also studied. It was shown that aminopterin itself causes a severe damage upon the nuclei of the tumor cells by an intraperitoneal administration of 1mg/kg, but the other simpler pteridines showed no remarkable effect upon animals within, the dosage of 10-100mg/kg.
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愛甲 軍雄, 尾張 栄彦, 鳥越 政弘
1952 年 72 巻 10 号 p.
1297-1300
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
We synthesized methyl-
bis-β-chloroethylamine
N-oxide and found that its effect upon the Yoshida ascites sarcoma is far more surpassing than methyl-
bis-β-chloroethylamine (HN
2). We also recognized that it changes in its aqueous solution (pH 8) to
N-β-chloroethyl-dimethylene-1, 2-oxaimine-
N-methochloride within several hours at a room temperature and then secondarily to
N, N-methyl-β-chloroethyl-O-β-chloroethylhydroxylamine.
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Synthesis of Iodinin
吉岡 一郎, 喜谷 喜徳
1952 年 72 巻 10 号 p.
1301-1303
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
Iodinin was synthesized by the oxidation of 1, 6-dihydroxyphenazine with H
2O
2 and acetic anhydride in benzene solution.
N-oxidation of 1- and of 2-hydroxyphenazine was also investigated.
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津田 恭介, 早津 了一
1952 年 72 巻 10 号 p.
1303-1310
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
Cholesteryl tosylate, when refluxed with pyridine and α-picoline, forms pyridinum and picolinium salts which yield, upon low pressure-distillation, C
32H
49N and C
33H
51N, respectively. Cholesteryl tosylate and γ-picoline, 2, 6-lutidine, or 2, 4, 6-collidine, do not form salts upon similar refluxing, but yield respective bases, C
33H
51N, C
34H
53N, and C
35H
55N. The authors clarified the structures of these weakly basic amines and confirmed that the cholestenyl group was bonded to the γ-position of pyridine, and in the methyl of α- and γ-picoline. The phenomenon of the alkyl transiting from the nitrogen to the methyl is an entirely new reaction observed for the first time.
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Paper Chromatographic Studies of Rhubarbs. (1)
柴田 承二, 瀧戸 道夫
1952 年 72 巻 10 号 p.
1311-1314
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
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Über die Druckhydrierung des 4-Nitropyridin-N-oxydes
石井 輝司
1952 年 72 巻 10 号 p.
1315-1316
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
4-Nitropyridin-
N-oxyd wird durch die Druckhydrierung mit Raney-Nickel oder Nickel-formiatparaffin (bei pH ca. 3-4) als Katalysator in methanolischer Lösung in das 4-Aminopyridin als Hauptprodukt übergeführt, wenn man unter der Reaktionstemp. von 160-170° resp. 100-110° arbeitet. Falls man dabei das Raney-Nickel verwendet, so entsteht als Nebenprodukt das Azoxy-, das Azo-pyridin-
NN′-dioxyd, das 4-Pyridon und das
N-Methylpiperidin and ausserdem das Ammoniak, je nach der Reaktionstemp. Dagegen kommt bei der Anwendung vom Nickelformiatparaffin kein Nebenprodukt zur Entstehung.
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Uuml;ber die Druckhydrierung des 4-Nitro-, 4-Oxy-, und 4-Methoxy-chinoiin-N-oxydes
石井 輝司
1952 年 72 巻 10 号 p.
1317-1324
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) 4-Nitrochinolin-
N-oxyd wird durch die Druckhydrierung mit Raney-Nickel oder Nickelformiatparaffin (bei pH 4) als Katalysator in methanolischer Lösung (bei 50-74°) in das 4-Aminochinolin, jedoch mit schlechter Ausbeute, resp. (bei 120-140°) in das 4-Amino-Bz-tetrahydrochinolin mit guter Ausbeute übergeführt.
2) 4-Oxychinolin-
N-oxyd wird durch die Druckhydrierung mit Raney-Nickel in methanolischer Lösung in das 4-Oxychinolin (bei 40-55°) und 4-Oxy-Bz-tetrahydrochinolin (bei 160-240°) als Hauptprodukt mit guter Ausbeute übergeführt, und daneben auch das Py-Tetrahydrochinolin, das
cis-
N-Methyldekahydrochinolin und das
N-Methyl-Py-tetrahydrochinolin, je nach der Reaktionstemp., erfasst.
3) 4-Methoxychinolin-
N-oxyd wird durch die Druckhydrierung mit Raney-Nickel in methanolischer Lösung in das 4-Methoxychinolin (bei 40-50°) und das 4-Methoxy-Bz-tetrahydrochinolin (140-260°) als Hauptprodukt mit guter Ausbeute übergeführt, und daneben auch in das
cis-
N-Methyldekahydrochinolin und das
N-Methyl-Py-tetrahydrochinolin, je nach der Reaktionstemp., erfasst.
4) 4-Methoxychinolin wird bei der Druckhydrierung mit Raney-Nickel unter Zusatz von Nickelchlorid in methanolischer Lösung nur zum Teil von einer Umlagerung begleitet, wobei das
N-Methyl-4-chinolon gebildet wird.
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浮田 忠之進, 積田 亨
1952 年 72 巻 10 号 p.
1324-1327
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The fraction of diterpenic acid, which had previously been isolated from the fruits of
Juniperus japonica, was reinvestigated and two isomers were obtained in a pure state. The one was a new diterpenic acid, C
20H
30O
2, and the other was found to be identical with 7-isodextropimaric acid.
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Reimer-Tiemann Reaction of 1-Methyl-2-hydroxy-5, 6, 7, 8-tetrahydronaphthalene
浮田 忠之進, 野島 庄七, 長沢 金藏
1952 年 72 巻 10 号 p.
1327-1332
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1-Methyl-2-hydroxy-5, 6, 7, 8-tetrahydronaphthalene was treated under the conditions of the Reimer-Tiemann synthesis, resulting in two new products. The structures of these compounds are discussed and it is concluded that the one possesses the structure of 1-methyl-2-hydroxy-3-aldehyde-5, 6, 7, 8-tetrahydronaphthalene and the other, 1-methyl-1-dichloromethyl-2-keto-1, 2, 5, 6, 7, 8-hexahydronaphthalene.
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Dibenzofuran Derivatives. (1)
柴田 承二, 名取 信策, 角 保男
1952 年 72 巻 10 号 p.
1333-1336
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
A series of dibenzofuran derivatives which possess various substituents in 3- or 8-position was synthesized and their antibacterial activities were discussed. 3-Amino-and 3-guanidino-8-chlorodibenzofurans showed remarkable antibacterial effect against
Mycobacterium tuberculosis A. T. C. C. No. 607.
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菅沢 重彦, 伴 義雄
1952 年 72 巻 10 号 p.
1336-1339
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1-Methyl-3-ethylpyridinium methosulfate, when treated with alkaline potassium ferricyanide, gave a single oxidation product. Its constitution was established as 1-methyl-3-ethyl-2-pyridone, since by chlorination followed by oxidation it was converted into 2-chloropyridine-3-carboxylic acid of m. p. 193° (vigorous effervescence!), not identical with the authentic 2-chloropyridine-5-carboxylic acid.
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Crystallographic Study on Santonin and its Related Compounds
三橋 博
1952 年 72 巻 10 号 p.
1339-1342
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
The refractive index and optical axial angle were found to be most useful for microchemical detection. Under a polarized microscope, santonin, β-santonin, artemisin, and ψ-santonin could easily be distinguished. Santonin shows a very strong dispersion and its value of optical axial angle is 2V=26°(+). Consequently, the presence of santonin in Artemisia plant could easily be determined by this measurement. Crystallographic data of α-hydroxysantonin, hyposantonyl quinol, ψ-santonin, monobromosantonin,
l-α-desmotroposantonin acetate, and santonic acid were determined.
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Syntheses and Antiviral Effects of 3-Phenylazo-4-hydroxynaphthalene Sulfonic Acid and Its Derivatives
上田 武雄, 豊島 滋, 伊藤 知男
1952 年 72 巻 10 号 p.
1343-1346
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) 3-Phenylazo-4-hydroxynaphthalene selfonic acid and its derivatives were synthesized by diazotizing aniline and its ring-substitutes and coupling the resulting diazonium compounds with α-naphthol sulfonic acid-(4).
2) These compounds were tested as to their activities
in vitro against the Nakayama strain of
Encephalitis japonica.
3) 3-(
p-Methylphenylazo)-4-hydroxynaphthalene selfonic acid possessed a remarkable activity against the virus among the series of 3-phenylazo-4-hydroxynaphthalene sulfonic acid.
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Syntheses and Antiviral Effects of 3-Phenylazo-4-aminonaphthalene Sulfonamide and Its Derivatives
上田 武雄, 豊島 滋, 和智 恒雄, 檜山 実, 谷口 三春
1952 年 72 巻 10 号 p.
1346-1350
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
(1) 3-Phenylazo-4-aminonaphthalene sulfonamide and its derivatives were synthesized by diazotizing aniline and its ring-substitutes and coupling the resulting diazonium compounds with 4-aminonaphthalene sulfonamide-(1) and its
N1-substitutes.
(2) These compounds were tested as to their activities
in vitro against
Encephalitis japonica.
(3) Among the series of 3-phenylazo-4-aminonaphthalene sulfonamides,
p-(3-phenylazo-4-aminonaphthalenesulfonamido)-benzoic acid showed the most marked activity against the virus, approximately 15 times that of sodium 3-phenylazo-4-aminonaphthalene sulfonate, and the relatively low toxicity. This drug is of promise for the
in vivo test.
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Chemotherapeutic Effect of p-(3-Phenylazo-4-aminonaphthalenesulfonamido)-benzoic Acid (PANS-No. 325) against Neurotropic Viruses
上田 武雄, 豊島 滋, 和智 恒雄, 檜山 実, 谷口 三春
1952 年 72 巻 10 号 p.
1351-1354
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1)
p-(3-Phenylazo-4-aminonaphthalenesulfonamido)-benzoic acid shows a remarkable effect on the Japanese encephalitis virus and the Col. SK virus
in vitro and
in vivo, with a low toxicity.
2) It is assumed that the antiviral effect of
p-(3-phenylazo-4-aminonaphthalenesulfonamido)-benzoic acid might be caused by a direct interaction between the compound and viruses.
3) It is doubtful whether the compound possesses neurotropy, cerebrotropy, and penetration-power into cells.
4) Chemoprophylactic effect of the compound may be expected because of its direct interaction with viruses.
5)
p-(3-Phenylazo-4-aminonaphthalenesulfonamido)-benzoic acid is of promise for clinical uses.
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Syntheses and Antiviral Effects of 3-Phenylazo-4-hydroxynaphthalene Sulfonamide and Its Derivatives
上田 武雄, 豊島 滋, 伊藤 知男
1952 年 72 巻 10 号 p.
1354-1359
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) 3-Phenylazo-4-hydroxynaphthalene sulfonamide and its derivatives were synthesized by diazotizing aniline and its ring-substitutes, and coupling the resulting diazonium compounds with 4-hydroxynaphthalene sulfonamide and its
N1-substitutes.
2) These compounds were examined as to their activities
in vitro against the Nakayama strain of
Encephalitis japonica.
3) Among these compounds,
o- and
p-[3-(
p-methylphenylazo)-4-hydroxynaphthalenesulfonamido]-benzoic acid possessed the effects approximately equal to that of
p-(3-phenylao-4-aminonaphthalenesulf onamido)-benzoic acid, which were proved to possess the strongest effects
in vitro and
in vivo among all known substances active against neurotropic virus
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Antiviral Effects of Naphthoquinone Derivatives
上田 武雄, 豊島 滋, 伊藤 知男
1952 年 72 巻 10 号 p.
1360-1363
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) Naphthoquinone derivatives and 1, 4-naphthoquinone-4-anil derivatives were examined as to their activities
in vitro against
Encephalitis japonica.
2) Potassium 1, 2-naphthoquinone-3-phenylazo-4-sulfonate and 2-hydroxy-1, 4-naphthoquinone-4-anil possessed weak antiviral activities, but this series generally did not show any remarkable result.
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Automatization of Organic Analysis. (6). Automatic Apparatus for Micro-Dumas Method
坂本 秀策, 平井 通博
1952 年 72 巻 10 号 p.
1363-1367
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
Complete automatization of micro-Dumas method for nitrogen analysis was concluded by the automatic combustion apparatus devised by the authors. Desirable motion of the movable furnace was effected by the use of a cam of special design. By the use of this mechanism, the total analytical time has been shortened compared to the existing Pregl method, the procedure has been much simplified, and individual difference in analytical values has been eliminated. Samples that decompose at thigh temperatures, which were apt to be incompletely decomposed by the Pregl method and were the cause of error, could be analyzed easily and with good results.
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Hydroxynaphthalene Sulfonic Acid Derivatives; Syntheses and Tests for their Effects on Bacteria and Viruses
檜山 実
1952 年 72 巻 10 号 p.
1367-1370
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
(1) Twenty derivatives of hydroxynaphthalene sulfonic acid were synthesized, two of which were unknown substances in literature, and their properties have been made clear. (2) As the results of the examinations as to their antibacterial effects, it was found that three compounds, 1-naphthol-4-sulfonamide, 1-ethoxynaphthalene-4-sulfonamide, and
N-(3-hydroxy-4-oxo-1-naphthylidene)-naphthionic acid, possessed slight effects, but the others did not exert any effect at all. (3) As to their antiviral effects, it was found that two compounds, 1, 2-naphthoquinone-4-sulfonic acid and the naphthylid-enenaphthionic acid, showed effects approximately equal to that of naphthionic acid.
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Aminonaphthalene Sulfonamide Derivatives; Syntheses and Tests for their Effects on Bacteria and Viruses
檜山 実
1952 年 72 巻 10 号 p.
1370-1374
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
(1) Twenty-two derivatives of aminonaphthalene sulfonamide were synthesized, 17 of which were unknown substances in literature, and their properties have been made clear. As for two compounds, 1-acetylaminonaphthalene-4-sulfochloride and 1-acetylaminonaphthalene-4-sulfonamide, the author proposed the melting points different from those formerly reported. (2) As the results of antibacterial tests, all of these compounds were found weaker as to their activities than sulfanilamide and its dervatives. (3) As to antiviral effects, however, remarkable activities were recognized in three
N4-substituted derivatives of 1-aminonaphthalene-4-sulfonamide:
N4-Phenyl,
N4-(
o-carboxyphenyl), and
N4-(1′-naphthyl) derivatives.
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Naphthyiazohenzene Sulfonamide Derivatives; Syntheses and Tests for their Effects on Bacteria and Viruses
檜山 実
1952 年 72 巻 10 号 p.
1374-1377
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
(1) Twenty-three derivatives of naphthylazobenzene sulfonamide were synthesized, 15 of which were unknown substances in literature, and their properties have been made clear. (2) Antibacterial effects of these above compounds were found inferior to that of sulfanilamide. (3) As for antiviral effects, activities approximately equal to that of naphthionic acid were recognized in
p-(1-amino-4-sulfo-2-naphthylazo)-benzene sulfonamide,
p-(2-amino-3, 6-disulf o-1-naphthylazo)-benzene sulfonamide, and
p-(1-hydroxy-8-amino-3, 6-disulf o-2-naphthylazo)-benzene sulfonamide, among which the first compound with an amino and a sulfo radicals in the naphthalene ring, was the most active. It should also be noted that the azo derivatives with sulfanilamide as the diazo component, exerted antiviral effects, while the others with such diazo component as sulf apyridine, self athiazole, or sulf apyrimidine, showed almost none.
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bis (Naphthylazophenyl) Sulfone Derivatives; Syntheses and Tests for their Effects on Bacteria and Viruses
檜山 実
1952 年 72 巻 10 号 p.
1378-1380
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
1) Nine derivatives of
bis (naphthylazophenyl) sulfone were synthesized, all of which, except one, are unknown substances in literature, and their properties have been made clear.
2) As a result of antibacterial tests,
bis [
p-(1-amino-4-sulfo-2-naphthylazo) phenyl] sulf one and
bis [
p-(1-amino-4-selfamyl-2-naphthylazo) phenyl] sulfone, were found to possess effects similar to that of sulfanilamide.
3) As for antiviral effects, the 2 said compounds were also found effective on the virus. It is of interest that these 2 compounds showed considerable activities against both bacteria and viruses.
4) Antibacterial and antiviral properties of derivatives of naphthalene sulf onic acid hitherto synthesized were reviewed, and it was found that many compounds of this series possessed antiviral activitis more marked than that of naphthionic acid, and it was also concluded that derivatives of
bis (naphthylazophenyl) sulfone might be of promise for a wide range of microbial diseases.
5) It seems possible to obtain, by syntheses, more effective antiviral drugs in future, judging from the fact that compounds possessing antiviral activities were found by these studies.
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根来 玄忠
1952 年 72 巻 10 号 p.
1381-1383
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
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柳田 昌一
1952 年 72 巻 10 号 p.
1383-1384
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
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Quantitative Determination of Crude Filicin
原田 利一
1952 年 72 巻 10 号 p.
1384-1386
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
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A New Detection Method for Flavanones
柴田 承二, 笠原 昭
1952 年 72 巻 10 号 p.
1386-1388
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
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藤田 路一
1952 年 72 巻 10 号 p.
1388-1390
発行日: 1952/10/25
公開日: 2010/02/19
ジャーナル
フリー
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1952 年 72 巻 10 号 p.
e1a
発行日: 1952年
公開日: 2010/02/19
ジャーナル
フリー
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1952 年 72 巻 10 号 p.
e1b
発行日: 1952年
公開日: 2010/02/19
ジャーナル
フリー