-
Seizo Kanao, Kiyoshi Shinozuka
1948 Volume 68 Issue 10-12 Pages
258-261
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
The ketone compound obtained by the reaction of methylamine and bromo-
p-methoxypropiophenone was catalytically reduced with PtO
2⋅H
2 and a normal base of
p-methoxyephedrine was quantitatively obtained. By the use of amalgamated Na and 2N-HCl, normal and iso compounds were obtained in a ratio of 3:1. N-Benzoyl derivative of
p-methoxy-ephedrine gives ester of benzoic acid by treatment with mineral acid and subsequent alkaline saponification yields
p-methoxy-iso-ephedrine. Emde's degradation of the iodide of methylated quarternary base of
p-methoxy-iso-ephedrine results in obtaining (β)
p-methoxyphenyl-propyleneglycol, m.p. 116°, (β) being in iso compound.
View full abstract
-
Seizo Kanao, Kiyoshi Shinozuka
1948 Volume 68 Issue 10-12 Pages
261-265
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Normal base of β-amino-β-anisyl-isopropyl alcohol was obtained by the reaction of NH
3 and anethol-bromo-hydrine or anetholoxide with α-imino-bis-[
p-methoxyphenyl-β-hydroxypropane] as a by-product. Hydrolysis of anethol-ψ-urea by NaOH gives an iso-form whereas the base obtained from anethol-acetyl-ψ-urea is a normal compound. Normal base of β-methylamino-β-anisyl-isopropyl alcohol was obtained by the reaction of α-bromo-
p-methoxybenzyl methyl ketone and methylamine and subsequent catalytic reduction. A small amount of iso-base is obtained by the reduction with 5% amalgamated sodium and 2N-HCl. Normal base was also obtained by the reaction of methylamine and anethol-bromohydrine, and an iso compound from anethol-methyl-ψ-urea. The ammonium base expected was not obtained by shaking the primary and secondary normal bases with Mel and KOH solutions and tetramethylammonium iodide was here obtained. The original material scems to have transited from unsaturated carbinol to
p-methoxybenzyl methyl ketone. On the contrary, the iso compound is remarkably stable.
View full abstract
-
Seizo Kanao, Kiyoshi Shinozuka
1948 Volume 68 Issue 10-12 Pages
265-269
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Iso-base of
m, p-methylenedioxy-nor-ephedrine was obtained by the condensation of piperonal, nitromethane and KHCO
3 and subsequent reduction with Zn+H
2SO
4. The normal base does not separate out here and the compound obtained by Bruckner from nitrosite is also an iso-base. Reaction of alcoholic or aqueous NH
3 and isosafrol-bromohydrine or isosafrol oxide yielded normal-base of β-amino-β piperonyl-isopropyl alcohol with a by-product of α-imino bis-[
m, p-methylenedioxyphenyl-β-hydroxypropane] (hydrochloride, m.p. 227°). It is assumed that the hydrochloride of m.p. 154°, obtaind by Read and Reid, is a mixture of normal and iso compounds and the base obtained by Krassuski is a normal compound. Normal base of β-methylamino-β-piperonyl-isopropyl alcohol was obtained by the reaction of alcoholic or aqueous methylamine and isosafrol-bromohydrine or isosafrol oxide. By the alkaline saponification of isosafrol-methyl-Ψ-urea, only the iso-base was obtained. The base obtained by Mannich must be a normal compound.
View full abstract
-
Tatsuo Kariyone, Tomijiro Fukui, Tasaburo Kiguchi, Motaro Ishimasa, Ka ...
1948 Volume 68 Issue 10-12 Pages
269-271
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
“Mibuyomogi”,
Artemisia monogyna Waldst. et Kit. yielded, besides santonin, 2 new lactones, monoginin, C
15H
18O
3, m.p. 138°, and mibulactone, C
15H
22O
4, m.p. 228-9°, and a kind of acidic substance, artemisic acid, C
18H
36O
5, m.p. 108°.
View full abstract
-
Constitution of Artemisic Acid. 1
Tatsuo Kariyone, Tomijiro Fukui, Motaro Ishimasa
1948 Volume 68 Issue 10-12 Pages
271-272
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Artemisic acid, C
18H
36O
5, gives a triacetate. Its methyl ester has an m.p. 64.5°, anilide, m.p. 115°. Reduction with red phosphorus and hydriodic acid gives stearic acid. It is assumed, therefore, that artemisic acid is a kind of trihydroxy-stearic acid.
View full abstract
-
Tatsuo Kariyone, Tomijiro Fukui, Motaro Ishimasa
1948 Volume 68 Issue 10-12 Pages
272-275
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
By the oxidation of artemisic acid with Na
2Cr
2O
7+H
2SO
4, azelaic, glutaric, succinic, n-valeric and n-butyric acids were obtained. Oxidation by lead tetra acetate gave azelaic aldehyde acid and 5-hydroxypel-argonaldehyde, m.p. 68°. Azelaic acid was obtained by the oxidation of the former and, glutaric and succinic acids from the latter. The authors, therefore, suggest 9, 10, 14-trihydroxystearic acid as the constitution of artemisic acid.
View full abstract
-
Tatsuo Kariyone, Tomijiro Fukui
1948 Volume 68 Issue 10-12 Pages
275-276
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Friedel-Crafts reaction of decaline and acetyl chloride does not give acetyldecaline but is accompanied by dehydrogenation to give 5, 6, 7, 8-tetrahydronaphthyl-(2) methyl ketone (I). A substance that is easily nitrated is obtained by decaline and aluminum chloride so that, it can be assumed that decaline is dehydrogenated by aluminum chloride and then undergoes condensation to give (I).
View full abstract
-
Tatsuo Kariyone, Tomijiro Fukui, Hiroshi Nagata
1948 Volume 68 Issue 10-12 Pages
276-278
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
β-(
p-Nitnophenyl)-β-hydroxymethylacrylic lactone, decompn. 245°, is obtained by the nitration of β-phehyl-β-hydroxymethyl-acrylic lactone. Reduction of the former to an amino compound, decompn. 203-6°, and a subsequent diazotation give β-(
p-hydroxy-phenyl)-β-hydroxymethylacrylic lactone, m.p. 253-4°.
View full abstract
-
Masuo Murakami, Shigeru Oae
1948 Volume 68 Issue 10-12 Pages
278-282
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Boilig
p-rhodaniline with glacial AcOH and then reacting halogen result in the formation of
p-acetamino-benzene sulfohalide (I). It was found that this formation was due to concurrent hydrolysis at the time of acetylation of
p-rhodaniline, to which a halogen atom would react to give (I).
p-Rhodanacetanilide, which has not been hydrolysed would give 2-halogeno-4-rhodanacetanilide by the substitution of halogen atom in the nucleus.
View full abstract
-
Syntheses of Antibacterial Thiocarbocyanines
Yoshihisa Mizuno, Takashi Uyemura, Kazuo Shibata, Eiji Hase, Masujiro ...
1948 Volume 68 Issue 10-12 Pages
282-285
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
It has been found in Tamiya Laboratory, Botanical Inst., University of Tokyo, that benzothiocarbocyanines greatly inhibit the growth of staphylococci in comparatively minute quantities. In order to test bacteriostatic effects of its allied compounds having substituents at 8-position, syntheses of those compounds were planned. After observation of known synthetic methods, a novel simple method was found. By this means, 7 new kinds of benzothiocarbocyanine were synthesized in order to test their bactericidal action.
View full abstract
-
Taizo Matsukawa, Takeo Iwatsu, Shojiro Yurugi
1948 Volume 68 Issue 10-12 Pages
285-287
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
γ-Aceto-γ-acetylmercaptopropyl acetate (I), γ-aceto-γ-carbethoxy-mercaptopropyl acetate (II) and γ-aceto-γ-methylmercaptopropyl acetate (III) were synthesized. Heating (I), (II) and (III) respectively with 2-methyl-4-amino-5-formaminomethylpyrimidine hydrochloride in formic acid gives vitamin B
1 in cases of (I) and (II) but the condensation does not occur in the case of (III).
View full abstract
-
Takeo Tsukamoto, Takeo Ohtaki
1948 Volume 68 Issue 10-12 Pages
287-289
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Barks of mulberry used for drugs is believed to be derived from
Morus acidosa Griff. Alcoholic extract of the bark was concentrated and the precipitate that separated out on cooling was saponified with alcoholic potash and α- and β-amyrin and stearic acid were obtained. Isolation of β-amyrin from mulberry bark is worthy of notice.
View full abstract
-
Takeo Tsukamoto, Takeo Ohtaki
1948 Volume 68 Issue 10-12 Pages
289-291
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
The alcoholic extract of mulberry bark, from which the precipitate has been removed, was concentrated under vacuum and put to water distillation and obtained volatile oil (ca 0.07% of the material).
The non-volatile portion was dissolved in ether and shaken with 5% Na
2CO
3 and then with 2% KOH solutions. KOH solution contained a substance believed to be resinotannol. From the portion existing between ether and alkaline layers, sitosterol-
d-glucoside was obtained. Ether soluble portion was saponified with alcoholic potash and α-amyrin, sitosterol and pale yellow powder (probably resen of Tschirch's) were obtained from the neutral portion. Acid portion yielded palmitic and stearic acids.
View full abstract
-
Phospholipids. (2). Structure of Corynin of Chargaff's
Hideo Takahashi
1948 Volume 68 Issue 10-12 Pages
292-296
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Corynolic acid the so-called corynin, of Chargaff's, and dehydroxy-corynin were oxidized and their decomposition products were compared with compounds synthesized. As a result, following formula has been given to corynin.
CH
3-CH-(CH
2)
7-CH-(CH
2)
17-CH-(CH
2)
14-CH
3
View full abstract
-
Syntheses of Sulfaminopyrimidines. (1)
Taizo Matsukawa, Ken-ichi Seki
1948 Volume 68 Issue 10-12 Pages
296-297
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Several derivatives of sulfaminopyrimidine were synthesized by reacting various aromatic sulfonamides and 2-methyl (or ethyl)-mercapto-4-methyl-6-hydroxypyrimidine.
View full abstract
-
Shoji Shibata, Yoshiaki Miura, Tyunosin Ukita, Tomie Tamura
1948 Volume 68 Issue 10-12 Pages
298-300
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Antibacterial effects in vitro of usnic acid, a component of lichens of Usnea specie, and its derivatives were tested. Usnic acid and its derivatives have growth inhibitory actions against Gram-positive bacteria. Usnic acid inhibits the growth of avian type tubercular bacilli after 10 days' incubation at 160, 000 dilution and that of
Staphylococcs aureus after 24 hours at 160, 000-320, 000 dilution. Antibacterial activities against avian tubercular bacilli of usnic diacetate and dihydro-usnic acid are 1/2 to 1/4 that of usnic acid, this decreasing to 1/16 in that of dihydro-usnic acid diacetate (Table I.). These experiments prove that the antibacterial activity of usnic acid is controlled by the presence of 2 hydroxyl radicals and α, β-unsaturated ketone.
View full abstract
-
Comparative Studies on Antibacterial Effects of Various Types of Lichen Substances
Shoji Shibata, Yoshiaki Miura, Hisako Sugimura, Yuri Toyoizumi
1948 Volume 68 Issue 10-12 Pages
300-303
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Representative components of various lichen substances, according to the classification forwarded by Prof. Asahina, were chosen to test their growth inhibitory actions in vitro against bacteria. Antibacterial effect against Gram-positive bacteria were found with compounds of lichesterinic acid series and depsides of orcinol series where there were a large number of carbon atoms in their alkyl radical. No such properties were found with fatty acids of caperatic acid type, zeorin series compounds, depsides of β-orcinol series and depsidones. None showed any antibacterial action against Gram-negative bacteria.
View full abstract
-
Antibacterial Effects of Didymic Acid and Related Compounds
Shoji Shibata, Yoshiaki Miura, Hisako Sugimura, Yuri Toyoizumi
1948 Volume 68 Issue 10-12 Pages
303-305
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
Remarkable antibacterial action against Gram-positive bacteria were shown by didymic and decarbo-nordidymic acids belonging to the dibenzofuran derivatives of lichen substances. Comparison with other dibenzofuran derivatives showed that their antibacterial activity was controlled by their dibenzofuran nucleus, hydroxyl groups and the number of C-atoms of alkyl groups attached to it.
View full abstract
-
2-Aminovinylbenzothiazole Ethiodide
Torizo Takahashi, Hiroshi Yanagihara
1948 Volume 68 Issue 10-12 Pages
305-307
Published: June 10, 1949
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
The following 2-aminovinyl-benzothiazole ethiodide were prepared to use them as chemotherapeutic remedies. When condensed 2, 2′-dimethoxy-diphenyl-formamidine upon 2-methyl-benzothiazole ethiodide (I). 2-{ω-[
o-methoxy-anilido]-vinyl}-benzothiazole ethiodide of m.p. 232° (decomp.) is readily obtained The ethiodide (I) also combines with 4, 4′-diethoxy-diphenyl-formamidine at about 90° to form 2-{ω-[
p-diethoxy-anilido]-vinyl}-benzothiazole ethiodide of m.p. 194-196° (decomp.) and 3, 3′-diethyl-2, 2′-trimethine-benzothiazolocyanine (3) iodide (II) of m.p. 268° (decomp), while at about 110° chiefly the latter dyestuff (II). Again, on heating the ethiodide (I) respectively with 5, 5′-dichloro-2, 2′-dipyridylformamidine, 5, 5′-dibromo-2, 2′-dipyridyl-formamidine and 5, 5′-diiodo-2, 2′-dipyridyl-formamidine, 2-{ω-[5′-chloropyridyl-(2′)-amino]-vinyl}-benzothiazole ethiodide of m.p. 236° (decomp.), 2-{ω-[5′-bromopyridyl-(2′)-amino]-vinyl}-benzothiazole ethiodide of m.p. 239° and 2-{ω-[5′-iodopyridyl-(2′)-amino]-vinyl}-benzothiazole ethiodide of m.p. 236-9°, are produced.
View full abstract