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Takashi Isshiki, Tetsuo Inoue, Michio Nakanishi
1950 Volume 70 Issue 10 Pages
531-534
Published: October 25, 1950
Released on J-STAGE: February 19, 2010
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In order to test their antibacterial action, following derivatives of
p-gnanylphenyl-sulfonamides and their related compounds were synthesized:
N1-methyl, -pyridyl, -dimethylpyrimidyl, -thiazolyl, -methylthiazolyl, and -thymol. The physical constants of these compounds are given in Tables.
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Chloromethylation of Benzoic Acid Derivatives. (1)
Taizo Matsukawa, Kenzo Sirakawa
1950 Volume 70 Issue 10 Pages
535-537
Published: October 25, 1950
Released on J-STAGE: February 19, 2010
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Methyl benzoate and benzoic acid were chloromethylated in concentrated sulfuric acid by paraformaldehyde and hydrochloric gas. It was found that in both compounds the chloromethyl radical was introduced into the meta-position.
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Chloromethylation of Benzoic Acid Derivatives. (2)
Taizo Matsukawa, Kenzo Sirakawa
1950 Volume 70 Issue 10 Pages
538-540
Published: October 25, 1950
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2-Methylbenzoic and 4-chlorobenzoic acids were treated with paraformaldehyde and hydrochloric gas in a concentrated sulfuric acid solution. The chloromethylated compounds obtained in this case were 2-methyl-5-chloromethylbenzoic acid from the former, and 4-chloro-3, 5-dichloromethylbenzoic acid from the latter.
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Improved Method for the Synthesis of 2-Methylbenzothiazole Derivatives
Yoshihisa Mizuno, Kiyoshi Watanabe
1950 Volume 70 Issue 10 Pages
540-543
Published: October 25, 1950
Released on J-STAGE: February 19, 2010
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Conditions of reaction during synthesis of 2-methyl-benzothiazole through thioacetanilide was found to be as follows: 8% alkaline solution of thioacetanilide is added dropwise into supersaturated solution of potassium ferricyanide, with violent agitation. Extraction of the base following the reaction is preceeded by salting out with anhydrous sodium carbonate by which the yield on the base could be raised to 70% of the theory. This improved method of synthesis gives satisfactory results in the oxidation of thioacetanilide derivatives possessing anionoid group (e.g. methoxyl, methyl, chloro, etc.) in the para position, but those in which these groups are present in the ortho position or those possessing cationoid group (e.g. nitro) in the para position did not give as satisfactory an yield.
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Synthesis of Antibacterial Thiocarbocyanines
Yoshihisa Mizuno, Takashi Uemura
1950 Volume 70 Issue 10 Pages
543-545
Published: October 25, 1950
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Antibacterial power
in vitro of 10 kinds of newly synthesized thiocarbocyanine were examined. It was found that benzothiocarbocyanine possessing a substituent at 8-position had powerful bactericidal power against
Staphylococcus aureus Terashima. Of such compounds, the one with 2, 4-dihydroxyphenylvinyl radical at 8-position showed complete inhibition of growth of
Staph. aureus in a concentration of 10. exp (-6.7)g. per cc.
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Reductive Acylamination of Oximes
Minoru Sekiya
1950 Volume 70 Issue 10 Pages
545-548
Published: October 25, 1950
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In the manner similar to the case of the nitriles as reported in II, oximes were hydrogenated over nickel catalysts at high temperature and high pressure in the presence of formamide or ethyl formate. Experiments were carried out used as oximes benzaldoxime,
p-sulfonamidobenzaldoxime, acetaldoxime,
n-butyraldoxime, acetoxime and acetophenoxime. Corresponding formylamino derivatives were regularly obtained but the yield was not as good as in the case of nitriles, except in the case of aromatic aldehydes.
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Reductive Acylamination of Carbonyl Compounds in the Presence of Ammonia
Minoru Sekiya
1950 Volume 70 Issue 10 Pages
548-551
Published: October 25, 1950
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Hydrogenation of carbonyl compounds over Raney nickel at high temperature and high pressure in the presence of ammonia and formamide gave formylamino derivatives. The carbonyl compounds used were benzaldehyde,
p-sulfonamidobenzaldehyde,
n-butyraldehyde, acetophenone and phenylacetone. The yield of formamides was good in aromatic carbonyl compounds, side reaction being suppressed. Yield of formylamino derivatives were comparatively poor from aliphatic carbonyl compounds.
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Reductive Acylamination of Nitriles. (2)
Minoru Sekiya
1950 Volume 70 Issue 10 Pages
551-552
Published: October 25, 1950
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Experimental data on the reductive acylamination of nitriles with amides or esters other than formic acid are given. Experiments conducted include acylamination of benzonitrile with acetamide and ethyl acetate,
p-sulfonamidobenzonitrile with urea, and 2-methyl-4-amino-5-cyanopyrimidine with ethyl lactate, by which the corresponding acylamino derivatives were obtained. However, results were comparatively poor.
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Minoru Sekiya
1950 Volume 70 Issue 10 Pages
553-554
Published: October 25, 1950
Released on J-STAGE: February 19, 2010
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Various types of aliphatic amines were formylated by formamide and ethyl formate. Acylation of benzylamine was carried out with formylmethylamine, formylethylamine, acetamide,
n-butyl formate and ethyl acetate.
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Minoru Sekiya
1950 Volume 70 Issue 10 Pages
555-557
Published: October 25, 1950
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Reductive formylamination of benzonitrile by formylmethylamine,
n-butyl formate and formamide was carried out at a temperature below that of the formylation of amines. The results of experiments are given in the text together with the author's opinion on its reaction mechanism.
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Syntheses of p-Hydroxybenezenesulfonamide Derivatives. (1)
Taizo Matsukawa, Syoiti Ban, Hazime Kawasaki
1950 Volume 70 Issue 10 Pages
557-561
Published: October 25, 1950
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p-Benzoxybenzene sulfochloride and 2-amino-4-methylpyrimidine, 2-aminopyridine, or 2-aminothiazoles were reacted in pyridine and corresponding
N1-heterocyclic substituted 2-
p-benzoxybenzene sulfonamides were synthesized. These were led to 2-
p-hydroxy-and 2-
p-acetoxy-benzene sulfonamide-
N1-heterocyclic substituted derivatives.
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Derivatives of Isoeugenol, Resorcinol and Salicylic Acid
Shigeo Senda, Takahashi
1950 Volume 70 Issue 10 Pages
561-564
Published: October 25, 1950
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Basic phenol alkyl ethers such as β-diethylaminoethyl 2-methoxy-4-propenylphenyl ether, β-diethylaminoethyl 2-methoxy-4-propenyl-6-allylphenyl ether, and β-diethylaminoethyl 2-allyl-6-carhomethoxy (ethoxy, allyloxy)-phenyl ether, were synthesized using allyl derivatives of isoeugenol, resorcinol and salicylic acid as the starting materials.
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Masa Ikuse
1950 Volume 70 Issue 10 Pages
564-567
Published: October 25, 1950
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Abnormal structures were observed in the stems of
Tricosanthes japonica Regel, in the radial margin of the xylem plate and around the inner phloem, as well as in the tissue of cortex. In these abnormal structures in the margin of the xylem and in the inner phloem there exist small vessels differentiated as a result of activity of secondary cambium cells. Such type of abnormal thickening does not correspond to any type hitherto described.
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Gen-ichiro Fukuchi, Kaneo Imai
1950 Volume 70 Issue 10 Pages
568-569
Published: October 25, 1950
Released on J-STAGE: February 19, 2010
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Folium Ketsumei, the dried leaves of
Cassia Tora L., was extracted with MeOH and a flavonol glycoside was obtained from the concentrated extract as light yellow needles, m.p. 225-6°, corresponding to the formula C
27H
30O
16⋅2H
2O. On hydrolysis with 5% H
2SO
4, it gave one mol. of kaempferol, m.p. 273-4° (tetracetate, m.p. 181-2°), and two mol. of glucose (phenylosazone, m.p. 212°). In order to determine the position of the hydroxyl group bonded to the sugar residue, the glycoside was methylated with CH
2N
2. The reaction product, on hydrolysis with 5% H
2SO
4, gave small needles, m.p. 148-150°, which did not show any depression of the melting point when fused with 3-hydroxy-5, 7, 4′-trimethoxyflavone, m.p. 150-151°. Thus the original glycoside was proved to be kaempferol-3-diglucoside.
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Hideo Okeda, Satoru Okada, Saburo Motoyoshi
1950 Volume 70 Issue 10 Pages
570-571
Published: October 25, 1950
Released on J-STAGE: February 19, 2010
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It has been found from present experiments that, of the two kinds of crystals known to exist of bis-acetosulfanilylthiazolone-imide-(2), i.e. of m.p. 190-240°, and of m.p. 130-3°, the one with higher m.p. gives crystals of m.p. 245° after treatment with anhydrous acetone, and that the same changes into crystals of m.p. 130-3° upon addition of glacial AcOH or water, these being crystals of a dihydrate.
Observations were also made on the reaction of bis-acetosulfanilylthiazolone-imide-(2) and guanidine carbonate and it was found that the use of chlorobenzene as a solvent gave the best yield of acetosulfathiazole and acetosulfaguanidine (Cf. Table I.).
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A New Strain of Bacillus Macerans
Shichiro Akiya, Tadao Watanabe
1950 Volume 70 Issue 10 Pages
572-576
Published: October 25, 1950
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A new strain of acetone-ethanol fermenting bacteria which gives crystalline dextrin was isolated. Examination of its microbiological characteristics showed the new strain of bacteria to be very similar to
Bacillus macerans. By a few days of culture at 40° in 10% potato gruel medium, and by addition of acetone to the fermenting liquid to 50%, amylase is precipitated. The optimal pH of this enzyme is 5.4, and the temperature, 50°. Digestion of starch paste with this enzyme gives crystalline dextrin with a 50% yield.
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A New Hexasaccharide
Shichiro Akiya, Tadao Watanabe
1950 Volume 70 Issue 10 Pages
576-578
Published: October 25, 1950
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Digestion of starch by the newly isolated bacteria gave a new crystalline dextrin hexasaccharide which was methylated. This methylation by ordinary means gave a crude methyl compound containing 32% of CH
3O radical, which was brought to a completely methylated compound by treatment with metallic sodium in liquid ammonia to Na saccharate with subsequent treatment with CH
3I. The methyl compound wes obtained as needle crystals containing 1.5mol. ether of crystallization when recrystallized from ether. This crystal gradually effloresced in air. Crystals not containing ether melted at 98-103°, with [α]
D=+160.5° (in CHCl
3).
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Structure of the New Hexasaccharide
Shichiro Akiya, Tadao Watanabe
1950 Volume 70 Issue 10 Pages
579-582
Published: October 25, 1950
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Chemical structure of the methylated compound of the new hexasaccharide (new crystalline dextrin) was examined and it was found to be a oligosaccharide in which 6mol. of 2, 3, 6-trimethylglucopyranose were bonded in a ring form, similar to the previously reported hexasaccharide.
Treatment of the completely methylated compound of the new saccharide with conc. HCl at a low temperature gives trimethylglucose, which can be assumed to be its structural components, in a 93% yield. This compound gives an m.p. of 114°, [α]
D=+90°. Its chemical examination revealed that it posseses an oxygen bridge between C
1 and C
5, and a free OH radical at C
4, so that the structure was proved to be 2, 3, 6-trimethyl-glucopyranose.
Changes in the α
D value of the saccharide was examined by its hydrolysis with 50% H
2SO
4 at a room temperature and a temporary increase in α
D value was observed which is the specific characteristics of cyclic polysaccharides as stated by Freudenberg. From these facts, the new compound was assumed to be a cyclic hexasaccharide.
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Tadao Watanabe
1950 Volume 70 Issue 10 Pages
582-584
Published: October 25, 1950
Released on J-STAGE: February 19, 2010
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Both the previously reported saccharide (Schardinger's dextrin) and the new saccharide (new crystalline dextrin) were found to be oligosaccharides composed of 6mol. of glucose and no difference in their respective chemical structures could be observed. Observations were made in the present experiment from the point of enzymatic chemistry on their α- and β-bonding, and a difference between the two saccharides was revealed. By respective treatment of the two substances with maltase, which cleaves at α-bonding, and β-amylase, which cleaves at β-bonding, following results were obtained:
1) The hexasaccharide (Schardinger's dextrin) is decomposed only by maltase.
2) The new hexasaccharide forms glucose and maltose by the respective action of maltase and β-amylase.
From these results, it has become clear that, in the hexasaccharide (Schardinger's dextrin), the glucose molecules are bonded in α-bonding alone, while in the new saccharide, they are bonded both in α- and β-bondings. It can therefore be assumed that the only difference existing in the two saccharides is the difference in the manner of bonding.
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[in Japanese]
1950 Volume 70 Issue 10 Pages
585-589
Published: October 25, 1950
Released on J-STAGE: February 19, 2010
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Toshio Furukawa, Osamu Nagase
1950 Volume 70 Issue 10 Pages
590-591
Published: October 25, 1950
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1950 Volume 70 Issue 10 Pages
592-594
Published: October 25, 1950
Released on J-STAGE: February 19, 2010
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