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Eisaku Hayashi
1951 Volume 71 Issue 4 Pages
213-217
Published: April 25, 1951
Released on J-STAGE: February 19, 2010
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Synthese von 4-Aminopyridin-Derivaten
Tetsuzo Kato, Michitoshi Ohta
1951 Volume 71 Issue 4 Pages
217-220
Published: April 25, 1951
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Kenkichi Tomita
1951 Volume 71 Issue 4 Pages
220-224
Published: April 25, 1951
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1)
N-Alkyl-3-amino-piperidines were synthesized through two different courses, the one starting from nicotinamide and the other, from 2-amino-pyridine.
2) Through the first course,
N-methyl-,
N-ethyl- and
N-isopropyl-3-amino-piperidines were obtained: through the second one,
N-methyl- and
N-ethyl derivatives.
3) The identities of
N-methyl- and
N-ethyl-3-amino-piperidines by the two courses were established by m.p. and mixed m.p. of their dipictrates.
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Synthesis of p-Nitro-acetophenone
Shigehiko Sugasawa, Norio Sugimoto, Jun-ichi Iwao, Yutaro Nakamura
1951 Volume 71 Issue 4 Pages
225-226
Published: April 25, 1951
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p-Nitro-acetophenone, an important starting material for the synthesis of chloramphenicol, was prepared from
p-amino-acetophenone by the Sandmeyer's reaction in a 65% yield. This method will be recommended for its simplicity in manipulation and also from the economical view-point.
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On the Structure of Biscoclaurine Alkaloids. (1). Cleavage of Isotetrandrine with Metallic Sodium in Liquid Ammonia and the Structure of Alkaloids in the Oxyacanthine-Berbamine Series
Masao Tomita, Eiichi Fujita, Fujio Murai
1951 Volume 71 Issue 4 Pages
226-234
Published: April 25, 1951
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The authors carried out the decomposition of isotetrandrine with metallic sodium in liquid ammonia. As a result, compounds corresponding to 1-(4′-methoxy-benzyl)-6, 7-dimethoxy-
N-methyl-1, 2, 3, 4-tetrahydroisoquinoline (VII) and 1-(4′-hydroxy-benzyl)-6-methoxy-7-hydroxy-
N-methyl-1, 2, 3, 4-tetrahydroisoquinoline (VIII) were obtained as the decomposition products. On the basis of this result, the authors confirmed that the structure of isotetrandrine is (III, R=CH
3). Accordingly, all structures of alkaloids in the oxyacanthine-berbamine series were determined.
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Antibacterial Properties of 3-Alkylated or 3-Acylated 4-Hydroxycoumarins and of a Related Pyrone
Tyunosin Ukita, Den-ichi Mizuno, Tomie Tamura, Tamio Yamakawa, Shoshic ...
1951 Volume 71 Issue 4 Pages
234-243
Published: April 25, 1951
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1) Several 4-hydroxycoumarins having acyl-groups in 3-position were tested as to their antibacterial properties against nine bacteria in several cultivating media in vitro.
The length of the acyl-side chains was found to be an important factor for the activity. 3-
n-Decanoyl derivative was found to be the most active compound. It could prevent the growth of
Staph. aureus in a dilution of 1:64000000 in Knight's medium.
2) Some 3-alkyl-4-hydroxycoumarins and 6-methyl-4-hydroxy-3-octanoylpyrone-2 were tested as to their activities in order to compare them with the above mentioned compounds.
Both the former, which lacks the tricarbonylmethane group, and the latter, which lacks benzene ring were less active compared with the corresponding 3-acyl derivatives.
3) The most active compound, 3-
n-decanoyl-4-hydroxycoumarin was tested as to its toxicity in mice.
4) 3-Acyl-4-hydroxycoumarins were tested as to a number of properties, which are commonly positive for detergents, such as surface activity and heamolytic power, but these tests were found to be negative.
5) The low antibacterial activities of 3-acyl-4-hydroxycoumarins when tested in serum broth may be due to the serum albumin present, which was found to antagonise the activity, while egg albumin was inert.
6) The influences of copper or cobalt ions, and cysteine, on the antibacterial activities of these 3-acyl derivatives were tested. No remarkable effects of these substances were found.
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Tozaburo Kurihara, Takuo Ito
1951 Volume 71 Issue 4 Pages
243-246
Published: April 25, 1951
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1. Eine neue Nitrierungs-Methode von Thioxanthon wurde mitgeteilt.
2. Vierunddreizig neue Derivate von Thioxanthon wurden synthetisiert. Diese Substanzen haben wir durch die Kondensation von Chloraminothioxanthon-Gruppe mit jedem der folgenden Stoffe: Methansulfonsäure, Halogenalkyl, Halogenacyl, Halogen-thiazol, -pyrimidin u.s.w. erhalten.
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Sakahiko Owari
1951 Volume 71 Issue 4 Pages
246-249
Published: April 25, 1951
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4-Hydroxylamino-4′-hydroxy-, 4-hydroxylamino-4′-amino-, 4-nitro-3-hydroxy-4′-amino- and 4-amino-3-hydroxy-4′-amino-diphenyl sulfones were prepared to investigate their bacteriostatic activities.
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Komei Miyaki, Kazuo Satake, Makoto Hayashi
1951 Volume 71 Issue 4 Pages
249-256
Published: April 25, 1951
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Masaru Hasegawa
1951 Volume 71 Issue 4 Pages
256-259
Published: April 25, 1951
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Die Bromierung des Chinaldins mit
N-Bromsuccinimid wurde unter verschiedenen Bedingungen versucht. Der Reaktionsverlauf wurde dabei von der Polarität der angewandten Lösungsmittel stark beeinflusst. In polaren Lösungsmitteln, wie Chloroform oder Aether, ist die Reaktionsgeschwindigkeit ziemlich gross und es entsteht hierbei hauptsächlich ω-Dibromchinaldin neben einer kleiner Menge ω-Tribromchinaldin. In den nicht polaren Lösungsmitteln, wie Benzol oder Tetrachlorkohlenstoff, vollzieht sich die Reaktion viel langsamer. Durch Bestrahlung mit Ultraviolettenstrahlen und durch Erhitzen auf 80-90° wurden dabei ω-Monobromchinaldin als Hauptprodukt neben ω-Dibromid erhalten. Die Trennung von ω-Bromiden wurde wegen ihrer verschidenen Basizität erzielt. Das Di- und Tri-bromid sind im Gegensatz zum Monobromid sowie zum Chinaldin in 5% iger Bromwasserstoff-Lösung unlöslich. Andererseits ist das Dibromid in 20% iger Salzsäure löslich, im Gegensatz zum Tribromid. Das Bromatom des Monobromides ist so beweglich, dass es beim Behandeln mit verd. Salzsäure in ω-Monochlorchinaldin übergeht.
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Synthese von 2′-Chlorderivaten der Cinchona-Alkaloiden
Eiji Ochiai, Goro Kobayashi, Masatomo Hamana, Tsutomu Sugasawa
1951 Volume 71 Issue 4 Pages
260-262
Published: April 25, 1951
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ar. -Mono-
N-oxyd des Chinins und Dihydrochinins wurden durch Einwirkung von Phosphoroxychlorid in Chloroform-Lösung je in das entsprechende 2′-Chlorderivat übergeführt. Hiermit ist ein neuer Weg zur Herstellung von 2′-substituierten Cinchona-Alkaloiden geöffnet worden.
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Ueber die Reduktion der aromatischen tertiaeren Aminoxyden mittels Phosphortrichlorid
Masatomo Hamana
1951 Volume 71 Issue 4 Pages
263-266
Published: April 25, 1951
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Pyridin- und Chinolin-
N-oxyd sowie ihre Nitro-, Oxy- und Amino-Derivate werden durch Erwärmen mit Phosphortrichlorid in Chloroform je in das entsprechende Tertiäramin reduziert. Als eine Nebenreaktion wurde die Ersetzung des 4-ständigen Nitrobzw. Hydroxyl-Gruppe durch die Chlor-Gruppe beim Chinolin-
N-oxyd bemerkt und besonders beim 4-Nitrochinolin-
N-oxyd nur das 4-Chlorchinoline erhalten. 4-Aminoderivat des Pyridin-bzw. Chinolin-
N-oxydes ist in Chloroform sehr schwer löslich, sodass nur ein Teil in das entsprechende Tertiäramin reduziert wird unter Regenerierung beträchtlicher Menge des Ausgangsmaterials. Diese Reaktion ist allgemein gültig und ist zur Desoxydation der aromatischen Aminoxyden geeignet.
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Kaneo Imai, Kiyoshi Furuya
1951 Volume 71 Issue 4 Pages
266-268
Published: April 25, 1951
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A glycoside was isolated from the leaves and the flowers of
Fagopyrum cymosum, Meisn. The yield was about 4.0% (May)-8.5% (October) of the leaves and about 8.0-13.0% (October) of the flowers. The aglycone of this glycoside is quercetin and the sugars were glucose and rhamnose. The thorough methylation of this glycoside with an excess of diazomethane and subsequent hydrolysis gave 3-hydroxy-5, 7, 3′, 4′-tetramethoxyflavone, proving that the original glycoside was quercetin-3-rhamnoglucoside, i.e. rutin. The identity was also confirmed by paper chromatography.
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Mitizo Asano, Tyunosin Ukita, Tomoyosi Komai
1951 Volume 71 Issue 4 Pages
268-272
Published: April 25, 1951
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1) The structure of a decomposition product, C
11H
16O
3, of citrinin which was first reported and named “Product A” by Raistrick, et al., was studied and it was confirmed positively to have the structure assigned by Cram (1948).
2) A reduction product of citrinin by zinc and acetic acid was reinvestigated, and it was proved that the product has a molecular formula C
26H
30O
10, probably formed by reductive condensation from 2 moles of citrinin.
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Steroids that constitutes the Fatty Oil. (1)
Kyosuke Tsuda, Bunsuke Umezawa
1951 Volume 71 Issue 4 Pages
273-278
Published: April 25, 1951
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The non-saponifiable matter of the oil from globefish ovaries was separated and purified. From this matter, besides cholesterol, was obtained a new substance, C
30H
46O
2, m.p. 115-116°, of possibly a steroid or triterpenoid series. It has no active hydroxyl or carbonyl, but possesses one active double bond. On bromination of cholesterol by Schönheimer's method, yellow crystals, C
54H
82, m.p. 239-240° (decomp.), were obtained which were assumed to be identical with bicholestatriene obtained by Hafez.
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Fatty Acids that Composes the Fatty Oil. (1)
Kyosuke Tsuda, Hung Shan-Hai
1951 Volume 71 Issue 4 Pages
279-282
Published: April 25, 1951
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Stearic, palmitic, oleic and linolic acids were isolated and confirmed from the saponification product of ovary oil of globefish. These fatty acids contain about an equal amount of saturated and unsaturated acids.
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Reducing Sugar isolated during Purification of the Poisonous Component
Kyosuke Tsuda, Masaaki Kawamura
1951 Volume 71 Issue 4 Pages
282-284
Published: April 25, 1951
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Upon isolation of the poisonous components of globefish ovaries, reducing sugar was found but it was very difficult to separate from the poison. The authors identified and confirmed this sugar to be
d-glucose by paper partition chromatography and formation of β-
d-glucose pentaacetate.
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2-Chloro-7-methoxyacridines with 2-N, N-diethyl-and 3-N, N-diethyl-cyclohexylenediamine, and N, N-diethyl-p-phenylenediamine in 5-Position of Acridine Ring
Osamu Tamemasa
1951 Volume 71 Issue 4 Pages
285-289
Published: April 25, 1951
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Syntheses of Fatty Acids with Naphthyl, Naphthomethyl and Benzyl Groups in α-Position and Their Antibacterial Action
Tyunosin Ukita, Osamu Tamemasa, Hiroko Motomatsu
1951 Volume 71 Issue 4 Pages
289-297
Published: April 25, 1951
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Caproic, caprylic, capric, lauric and myristic acids substituted with naphthyl, naphthomethyl and benzyl groups were synthesized and their antibacterial activities against
St. aureus and both human and avian types of tubercle bacilli were tested.
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Ueber das reaktive Verhalten der Nitrogruppe der Nitrochinolin-N-oxyden
Toshihiko Okamoto
1951 Volume 71 Issue 4 Pages
297-300
Published: April 25, 1951
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Die Reaktivität der Nitrogruppe im Benzol-Teil und in der 4-Stellung der Nitrochinolin-
N-oxyden gegen die nukleophile Substitution vergleichend untersucht. Bei der Umsetzung mit Natriummethylat wurde zwar die Nitrogruppe bei allen Fällen durch die Methoxylgruppe ersetzt, doch ist die Reaktion bei derselben im Benzol-Teil nur mit schlechter Ausbeute und unter Bildung von enormer Menge harzigen Produktes durchgeführt worden, im Gegensatz zur glatten Substituion bei derselben in der 4-Stellung. Ausserdem ist die Nitrogruppe in der 4-Stellung der Chinolin-
N-oxyden so reaktiv, dass sie beim Erhitzen mit konz. Salzsäure bzw. Bromwasserstoffsäure auf dem Waserbade mit dem Chlor-bzw. Bromatom und beim Erhitzen mit 40% iger Schwefelsäure mit der Hydroxylgruppe ausnahmslos ersetzt wird, während dieselbe im Benzol-Teil all diesen Reaktionen widersteht. Hiermit kann man die letztere von den ersteren leicht unterscheiden. Der induktive Effekt der
N-Oxyd-Gruppe scheint jedoch die Nitrogruppe im Benzol-Teil zu einigermassen beeinflussen, weil sie durch die Methoxylgruppe trotz schlechter Ausbeute ersetzbar ist, im Gegensatz zu derselben des entsprechenden Tertiäramins.
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Masao Tomita, Eiichi Fujita, Fujio Murai
1951 Volume 71 Issue 4 Pages
301-302
Published: April 25, 1951
Released on J-STAGE: February 19, 2010
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