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Volume 72, Issue 1
Displaying 1-50 of 53 articles from this issue
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Kensi Kobayasi1952 Volume 72 Issue 1 Pages 1-3
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFrom the alcoholic extract of the air-dried leaves of Hyptis capitata Jacq., a flavonol glucoside was obtained, besides potassium chloride, as yellow needles, m.p. 158-160° (anhydrate, m.p. 190-193°), corresponding to formula C27H30O15⋅4H2O. Hydrolysis of the glucoside with 5% sulfuric acid gave kaempferol, glucose and rhamr ose. Methylration of the glucoside with diazomethane, followed by hydrolysis with 5% sulfuric acid yielded an aglycone as yellow needles, m.p. 149-150°, which was proved different from 3, 7, 4′-trimethylkaempferol by mixed fusion. Difference in melting points showed that the aglycone could not be either 3, 5, 4′- (m.p. 283-284°) or 3, 5, 7-trimethylkaempferol (m.p. 280-281°). This led to the assumption that the aglycone must be 5, 7, 4′-trime-thylkaempferol and the original glycoside, kaempferol-3-rhamnoglucoside. In order to obtain material for comparison, 4′-benzyloxy-3-methoxy-5, 7-dihydroxyf lavone, yellow plates, m.p. 279-280°, was prepared by the method of Allan and Robinson, methylated with diazomethane to 4′-benzyloxy-3, 5, 7-trimethoxyf lavone, colorless needles, m.p. 155-156°, and debenzylated with conc. hydrochloric acid to 4′-hydroxy-3, 5, 7-trimethoxy-flavone, pale yellow plates, m.p. 280-281°. Acetate, m.p. 152-153°.View full abstractDownload PDF (574K) -
Kensi Kobayasi, Kazuo Hayashi1952 Volume 72 Issue 1 Pages 3-5
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe concentrated ethanolic extract of the air-dried leaves of Dryopteris oligophlebia C. Chr. yielded a flavonol glucoside as yellow fine needles of m.p. 156-158° (anhydrate, m.p. 191-193°), corresponding to the formula C27H30O15⋅4H2O. Hydrolysis of the glucoside with 5% sulfuric acid gave kaempferol, m.p. 278-279° (tetraacetate, m.p. 185-186°), glucose and rhamnose. In order to determine the bonding position of the sugar, the glucoside was methylated with diazomethane and hydrolyzed with 5% sulfuric acid. The aglycone here obtained was pale yellow needles of m.p. 149-150° which showed no depression of the melting point when fused with 3-hydroxy-5, 7, 4′-trimethoxyflavone, m.p. 149-150°. This showed that the original glucoside was kaempferol-3-rhamnoglucoside.View full abstractDownload PDF (538K) -
Wax from Leaves of Chamaecyparis obtusaTatsuo Kariyone, Hisanori Watanabe, Hirokazu Kadowaki1952 Volume 72 Issue 1 Pages 5-7
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA Wax of m.p. 67-72.5° was obtained in approximately 1.8% yield from the dried leaves of “hinoki”, Chamaecyparis obtusa Endl. The chemical constants of the wax are: acid value, 49.2; ester value, 171.8; ester value after acetylation, 214.8; iodine no., 18.6. Its saponification yielded 83% of acid substances and 9% of non-saponifiable matter. The acid substances are composed chiefly of juniperic and sabinic acids, and the non-saponifiable matter yielded myricyl alcohol and 1, 12-dodecanediol, m.p. 80-81°, besides a substance assumed to be n-nonacosane-10-ol.View full abstractDownload PDF (535K) -
Estolides of Hinoki Leaf WaxTatsuo Kariyone, Hisanori Watanabe, Hirokazu Kadowaki1952 Volume 72 Issue 1 Pages 7-9
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe wax from the leaves of Chamaecyparis obtusa was separated into acid and neutral estolides and the acid estolide was fractionated into various portions by chromatography and in petroleum solvents of various melting points. From the determination of acid and ester values of each portion, the molecular weight of the estolide and the mean molecular weight of the acid constituting the estolide were calculated. It was clarified from these values that the estolide is composed of three to five molecules of juniperic and sabinic acids.View full abstractDownload PDF (458K) -
Study of Konotegashiwa Leaf WaxTatsuo Kariyone, Hisanori Watanabe, Hirokazu Kadowaki1952 Volume 72 Issue 1 Pages 10-11
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSWhite wax of m.p. 78-79° was obtained in 0.5% yield from the leaves of Biota orientalis. The constants of the wax were: acid value, 17.8; saponification value, 225.7; ester value, 207.9. Saponification of the wax yielded 81% of acid component and 7% of non-saponifiable matter. The acid component was composed chiefly of juniperic acid with the presence of a small amount of sabinic acid, which were present as estolides. Pentatriacontane and a hexadecane-1, 16-diol of m.p. 87-88° were obtained from the non-saponifiable matter.View full abstractDownload PDF (343K) -
Study of Sawara Leaf WaxTatsuo Kariyone, Hisanori Watanabe, Hirokazu Kadowaki1952 Volume 72 Issue 1 Pages 11-13
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSWhite wax of m.p. 71-72° was obtained in 1.2% yield from the withered leaves of Chamaecyparis pisifera. The constants of the wax were: acid value, 34.2; saponification value, 165.2; ester value, 131; iodine no. 13. Saponification of the wax yielded 73% of acid component and 21% of non-saponifiable matter. The acid portion was composed chiefly of juniperic and sabinic acids which were present as their estolides. The non-saponifiable matter was composed chiefly of n-nonacosane-10-ol which is also contained in Juniperus chinensis and Chamaecyaris obtusa.View full abstractDownload PDF (573K) -
Tatsuo Kariyone, Mitsuo Takahashi, Kiyokazu Takaishi1952 Volume 72 Issue 1 Pages 13-16
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBerger and Bradley synthesized a large number of glycerol ethers of which 3-(2′-methylphenoxy) propane-1, 2-diol has been used as myostatic anesthetic under the trade name of Myanesin. The authors followed the similar procedure with glucosides instead of. glycerol ethers and prepared a large number of aromatic glucosides in order to compare their physiological actions. The preparation followed Dr. Shishido's improvement of Helferich's method in which α-glucosides were prepared with zinc chloride as a catalyst, and β-glucosides with p-toluenesulfonic acid as a catalyst, and 15 kinds of new compounds were obtained. The details of their physiological tests will be reported by Prof. Yamada of the Kyoto University and his co-workers but, as can be seen from the accompanying table, the results o f their animal tests showed that the glucosides have longer duration of action than the corresponding glycerol ethers and supplement the shortcomings of Myanesin. The difference in the physiological action between α- and β-glucosides is very slight.View full abstractDownload PDF (799K) -
Effect of 3-Alkyithiazolone-sulfanilylimide (2) and Allied Substances on the Growth Inhibition of M. tuberculosisYoshihiko Yasue1952 Volume 72 Issue 1 Pages 16-17
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe author compared the growth inhibitory action of the so-called imino- and aminotypes of methylated sulfathiazoles against Mycobacterium tuberculosis and proved that the former is four times as powerful as the latter. A similar study was made with 3-alkylthiazolone-sulfanilylimides and allied substances.View full abstractDownload PDF (358K) -
On β-Methylumbelliferone and its DerivativesYasushi Mashiko1952 Volume 72 Issue 1 Pages 18-21
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn the polarographic reduction of β-methylumbelliferone, its concentration and wave heights constitute a linear function. In the range of pH 7-10, polarographic halfwave potential and pH also constitute a similar linear function. These were experimentally found to be representable by the following equation: E1/2=-(1.767+0.032 pH) volt.
Umbelliferone (I), β-methylumbelliferone (II), α, β-dimethylumbelliferone (III), α-ethyl-β-methylumbelliferone (IV), and α-propyl-β-methylumbelliferone (V) all showed a simple wave at pH 10.3 and gave n=1 per molecule of polarographic reduction by dropping mercury electrode, their E1/2 being as follows: (I)-1.602v.; (II)-1.870v.; (III)-1.916v.; (IV)-1.920v.; (V)-|>1.920|v.View full abstractDownload PDF (516K) -
Michimasa Izumi, Isao Aiko, Makoto Yokoo, Hisanori Kimoto1952 Volume 72 Issue 1 Pages 21-26
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSCondensation of β-bromovinyl ether or acetate with sodium p-nitrothiophenoxide in absolute alcohol gives β-(p-nitrophenylmercapto)-vinyl ether or acetate which, by bromination, yield α, β-dibromo-β-(p-nitrophenylmercapto) -ethyl ether (Va) or acetate (Vc), respectively. By warming (Va) or (Vc) with an equivalent quantity of thiourea in dil. alcohol, 2-amino-5-(p-aminophenylmercapto) -thiazole is obtained. Condensation of glycerol-α-chlorohydrin with sodium p-nitrothiophenoxide gives 1-(p-nitrophenylmer-capto)-2, 3-dihydroxypropane (XII), which is oxidized to 1-p-nitrophenylsulfonyl-2, 3-dihy-droxypropane (XIII) with perhydrol in glacial acetic acid. (XII) and (XIII) are oxidized to p-nitrophenylmercaptoacetaldehyde (IX) and sulfonyl-acetaldehde (X), respectively, with lead tetraacetate in glacial acetic acid. The enol acetates of (IX) and (X), obtained by the acetylation of (IX) and (X) with acetic anhydride and glacial acetic acid, are tre atedwith one mole of bromine and condensed with thiourea by which 2-amino-5-(p-nitrophenylmercapto)-thiazole and -sulfonylthiazole are respectively obtained. The former can also be prepared from (IX) by bromination followed by condensation with thiourea. 2-Amino-5-(p-tolylmercapto)-thiazole and -sulfonylthiazole can also be prepared by the same method from 1-(p-tolylmercapto)- and 1-(p-tolylsulf onyl)-2, 3-di-hydroxypropane.View full abstractDownload PDF (1137K) -
Toyozo Uno1952 Volume 72 Issue 1 Pages 26-27
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSCrystallographic studies by X-rays were made of sodium L(+)-glutamate. These crystals belong to the rhombic system and the size of their unit cell is: a0=15.27Å, b0=18.02Å, c0=5.61Å, ρ=1.589. The space group of sodium L(+)-glutamate is D24-P-212121, and the equivalent point of these space groups is four. Since the number of molecules in one unit cell is eight, two kinds of crystallographically different sodium L(+)-glutamate are present in one unit cell.View full abstractDownload PDF (920K) -
Toyozo Uno1952 Volume 72 Issue 1 Pages 28-30
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSX-Ray analyses of the crystals of 5-nitrofurfural semicarbazone were carried out and the following results obtained:
1) The crystals belong to the monoclinic system and possess a cleavage. The lattice constants are as follows: a0=17.21Å, b0=7.91Å, c0=8.03Å, β=129°18′, ρ=1.546.
2) The space group of these crystals is C2h2-P21/m with four molecules per unit cell.
3) The molecule is approximately planar and is assumed to be distributed two by two approximately parallel to the reflection plane in a space surrounded by such a plane in an unit cell.View full abstractDownload PDF (1761K) -
Syntheses of 2-(5-Nitro)-furfurylidene Amines and 2-(5-Nitro)-furaldehyde SemicarbazonesHaruo Saikachi, Shigetaka Yoshina1952 Volume 72 Issue 1 Pages 30-32
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to find new chemotherapeutics possessing antituberculous activities from nitrofuran derivatives, condensation was carried out with 2-(5-nitro)-furaldehyde with semicarbazides and aromatic primary amines which were described as auxoantibacterial group in the previous papers. None of these synthetic 2-(5-nitro)-furaldehyde semi carbazones and furfurylidene derivatives showed the anticipated antibiotic activity against tubercle bacilli in vitro.View full abstractDownload PDF (760K) -
On the Thiamine Destructive Factor. (3)Taizo Matsukawa, Shojiro Yurugi1952 Volume 72 Issue 1 Pages 33-37
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAddition of primary amines to the aqueous solution of thiamine, in the presence of sulfurous acid, results in almost quantitative substitution of its thiazole portion with primary amines. Use of aniline and p-aminobenzoic acid as the primary amine, respectively yields N-[2-methyl-4-aminopyrimidyl-(5)]-methylaniline (I) and -methyl-p-aminobenzoic acid (IV), which are respectively identical with the substances obtained by the condensation of aniline or p-aminobenzoic acid with 2-methyl-4-amino-5-bromo-methylpyrimidine hydrobromide (III). This reaction also occurs with the use of indole, forming N-[2-methyl-4-aminopyrimidyl-(5)]-methylindole (V) from thiamine. (V) is identical with the substance obtained by the condensation of (III) and indole. The thiamine derivative substituted with pyridine or quinoline in its thiazole portion, i.e. N-[2-methyl-4-aminopyrimidyl-(5)]-methyl-pyridinium or -quinolinium compounds also form (I) in good yields in the presence of sulfurous acid and aniline. These results are quite similar to the state of decomposition of thiamine by the thiamine destructive enzyme and are of interest as a model experiment for enzymatic activity.View full abstractDownload PDF (955K) -
Artemisia kurramensis Qazilbash. (1)Toyohiko Kawatani, Sanaenosuke Fujita, Tadaro Ohno1952 Volume 72 Issue 1 Pages 37-41
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSStudies were made on the morphology, growth characters, growth and development, and santonin content of the genus Artemisia, majority of which belong to section Seriphidium, in order to find plants growable in Japan. A. kurramensis Qaz. of Pakistan was cultivated on trial and subsequent studies showed that its cultivation was possible. The optimal temperature of germination is 10-15°. The number of chromosomes in A. kurramensis is 2n=18, while that of santonin-free A. maritima growing side by side with the former, is 2n=36. Hence, these plants belong to two cytogenetically distinct species of Artemisia.View full abstractDownload PDF (1389K) -
Photosensitizing Dyes. (2)Torizo Takahashi, Kenzo Satake, Noboru Nomura, Koichi Yoshikawa, Masay ...1952 Volume 72 Issue 1 Pages 42-45
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSTwelve kinds of aminovinyl compounds were obtained by the application of methiodides or ethiodides of 2-picoline, 2, 6-lutidine, 2, 4-dimethyl (2-methyl-6-ethoxy) quinoline, 2-methylbenzothiazole and 2′-methyl-6-chloro (methoxy, ethoxy)-pyrido-2, 3:5′, 4′-thiazole to 2, 2′, 5, 5′-tetramethyldiphenylformamidine, 4, 4′-diethoxydiphenylformamidine and 5, 5′-diiodo-2, 2′-dipyridylformamidine. Eleven kinds of styryl dyes were prepared by the condensation of o-chlorobenzaldehyde, salicylaldehyde, m-nitrobenzaldehyde, p-dimethylaminobenzaldehyde and furfural to the methiodides or ethiodides of 2-picoline and 2, 6-lutidine.View full abstractDownload PDF (777K) -
Photosensitizing Dyes. (3)Kenzo Satake, Torizo Takahashi1952 Volume 72 Issue 1 Pages 46-51
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) Trimethine cyanines were prepared by the condensation of 2, 6-lutidine ethiodide, 2-methylbenzothiazole ethiodide and 2′-methyl-6-methoxypyrido-2, 3:5′, 4′-thiazole methiodide with 2-ω-(o, m′-dimethylacetylanilino)-vinylpyridine methiodide and 2′-ω-(o, m′-dimethylanilino)-vinyl-6-chloropyrido-2, 3:5′, 4′-thiazole methiodide.
2) β-Methyltrimethine cyanines and γ-bromopentamethine cyanines were obtained by the application of 2-methyl-5-chlorobenzoxazole ethiodide, 2-methylbenzothiazole methiodide and quinaldine methiodide to S-ethyl ether of isothioacetanilide, 2-β-ethylmercaptopropen ylben zothiazole ethiodlde, bromopropane dianil and 2-γ-bromo-δ-acetylanilino-α, γ-butadienylbenzothiazole methiodide.
3) Heptamethine cyanines were prepared by the reaction of pentadiene dianil and 2-ω-acetylanilino-α, γ, ε-hexatrienylbenzothiazole methiodide with 2, 4-dimethylthiazole methiodide and 6-ethoxyquinaldine methiodide.View full abstractDownload PDF (1088K) -
Synthesis of γ-n-Butyldihydroresorcinol and Summary of the Syntheses of γ-AlkyldihydroresorcinolsKoichi Nakazawa, Shin Matsuura1952 Volume 72 Issue 1 Pages 51-54
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSγ-n-Butyldihydroresorcinol was prepared by the same manner as previously reported from ethyl acetoacetate, n-caproyl chloride and acrylonitrile. A better result was obtained in the present experiment, the overall yield being 16.7% of the theoretical amount calculated from ethyl acetoacetate. The γ-alkyldihydroresorcinols thus obtained gradually change in the air which is assumed to be due to ring cleavage to form 5, 6-diketo acid by autoxidation.View full abstractDownload PDF (749K) -
Studies on Sexual Hormones. I. Studies on Sexual Hormone Assays. (1)Yosoji Ito, Bun-ichi Tamaoki, Masako Egusa1952 Volume 72 Issue 1 Pages 54-60
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSCritical observations were made, using modern statistical methods, on a quantitative assay of androgen based on the response of seminal vesicle and prostate. As a result, following conclusions were made:
1) The correlation coefficient between log dose and the cube root of SVP (seminal vesicle and prostate anterior and intramedial lobe weights) was certified as being significant, and this dose-response curve was regarded statistically as the linear regression equation.
2) only when the linearity of this dose-response curve was certified by the present experiment it becomes possible to apply the statistical methods on quantitative assay for this androgen determination.
3) The correlation coefficients were significant between the cube root of the mean value of SVP and PP (prostate posterior lobe) and between their weight in individuals.
4) An interesting result obtained was that testosteron injection clearly decreased the weight of adrenal glands of castrated rats as compared to those of the control animals.View full abstractDownload PDF (1121K) -
Haruya Shimada, Tokunosuke Sawada, Shinzo Fukuda1952 Volume 72 Issue 1 Pages 61-62
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA hydroxycoumarin glucoside, aesculin, is found in the bark of Aesculus hippocastanum L. cultivated in Europe. The present workers proved the presence of fraxetin, instead. of aesculin or aesculetin, in the bark of Aesculus turbinata Bl. growing wild in Japan (This Journal: 57, 618 (1937)). This compound might exist as its glucoside in the living plant but the confirmation of such was not made in the previous experiments. In the present series of experiments, however, fraxin was proved as a glucoside. The raw material was directly extracted with an organic solvent or extracted with water and obtained by the lead precipitation method. Fraxin thus obtained showed the m.p. of 209-210° by the former method and m.p. 200° by the latter, both being identical in properties and coloration as given in literatures. Methylation of fraxin followed by hydrolysis yielded 7-monomethylfraxetin, m.p. 195°, and its acetylation, 7-methyl-8-acetylfraxetin, m.p. 147.5-148°.View full abstractDownload PDF (359K) -
Fraxinus Spaethiana, F. intermedia and OthersHaruya Shimada1952 Volume 72 Issue 1 Pages 63-65
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFraxin or fraxetin is present in the bark of Fraxinus ornus L. or F. excelsior L., growing in Europe. In Fraxinus Sieboldiana Bl., F. japonica Bl., F. pubinervis Bl., and F. sambucina Koidz., growing in Japan, the present worker obtained aesculetin without exception (This Journal: 58, 185 (1938); 60, 200 (1940)). The presence of aesculetin was confirmed in plants other than the above, such as Fraxinus intermedia Nakai (I), F. Spaethiana L. (II), F. Sieboldiana Bl. var. augustata Bl. (III) and F. kantoensis Koidz. (IV). It was also found that fraxetin was present with aesculetin in (I)., The glycoside, aesculin, was also obtained in good yield from F. Sieboldiana Bl., from which only aesculin had been confirmed previously (loc. cit.). It is assumed that aesculetin, which had been found from other plants, was present in the living plants as its glycoside, aesculin.View full abstractDownload PDF (558K) -
Fraxinus mandshurica and F. excelsissimaHaruya Shimada1952 Volume 72 Issue 1 Pages 65-67
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe Fraxinus genus can be divided roughly into two groups of Fraxinus sect. Ornus and Fraxinus sect. Fraxinus. The eight kinds of the Fraxinus genus plants described up to the previous report all belong to the former, while F. mandshurica Ruprecht and var. japonica Max., belong to the latter. The aqueous extract of the latter does not show any fluorescence and appears as if they were a totally different species from the former. A crystalline substance of m.p. 172-173° was obtained from F. mandshurica and var. japonica which does not show fluorescence; gives an acetate of m.p. 140-141°, and a methyl ether of m.p. 74-75°. This substance is identical with fraxinol obtained by Späth (Ber. 70, 698 (1937)) from the bark of Fraxinus excelsior L.View full abstractDownload PDF (529K) -
Fraxinus verecunda KoidzHaruya Shimada1952 Volume 72 Issue 1 Pages 67-69
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFraxinus verecunda Koidz., a large tree that grows on the Ohmine mountain in Nara Prefecture (western part of Japan) belongs to F. sect. Fraxinaster and is totally different from F. sect. Ornus. The aqueous extract of its bark docs not show any fluorescence in which it resembles those of the same classification, F. Mandshurica Reprecht and its variety, var. japonica Max. Syringin, m.p. 192-193°, was obtained from the bark of F. verecunda. Its oxidation with potassium permanganate yielded glycosyringaic acid, m.p. 208°, whose hydrolysis gave syringaic acid, m.p. 205-206°. Syringin was first isolated from the bark of lilac, Syringa vulgaris L. From the fact that it had been found in the bark of F. verecunda belonging to the same Oleaceae family, it is assumed that syringin is widely distributed in the plants of Oleaceae. A kind of phytosterol of m.p. 134-135° (acetate, m.p. 115-116°) was also obtained with syringin. from the same plant This sterol is probably identical with the phytosterol, m.p. 134-135° (acetate, m.p. 117°) of C26H44O, obtained from the bark of Ligustrum vulgare by Zellnerr and Werner (Monatsch. 47, 151 (1926)).View full abstractDownload PDF (646K) -
Takashi Isshiki, Yutaka Kuwada1952 Volume 72 Issue 1 Pages 69-72
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to test their antiviral and antibacterial activities, monochloroacetyl derivatives of p-nitrophenylalkylamines and their related compounds were prepared. Their physical constants and antibacterial activities are given in Tables I and II, respectively. Of those tested, chloroacetyl-α-(p-nitrophenyl)-ethylamine and the corresponding β-compound (VII and VIII) are somewhat effective against Mycobacterium tuberculosis H 37.View full abstractDownload PDF (725K) -
Takashi Isshiki, Yutaka Kuwada1952 Volume 72 Issue 1 Pages 72-74
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to test their antiviral and antibacterial activities, dichloracetyl derivatives of p-nitrophenylalkylamines and their related compounds were prepared. Their physical constants and antibacterial activities are given in the Tables I and II, respectively.View full abstractDownload PDF (513K) -
Haruki Satoh1952 Volume 72 Issue 1 Pages 74-76
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSTwo sulfur-containing alkamine esters, p-diethylaminosulfonylbenzoyldiethylaminoethanol and p-ethylsulfonylbenzoyldiethylaminoethanol, can be obtained as their hydrochlorides by the application of the corresponding acid chloride to diethylaminoethanol in anhydrous benzene. These esters form crystalline salts with penicillin.View full abstractDownload PDF (576K) -
Tozaburo Kurihara, Jiro Kitamura1952 Volume 72 Issue 1 Pages 76-78
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSEleven new sulfur- or halogen-containing local anesthetics were prepared. They were alkamine esters or amidines of amino-, hydroxy-, or bromo-mercaptobenzoic acids. Eight. of these were found to be as effective as or slightly better than cocaine on rabbit cornea. Antibacterial action of the sulfa drugs against Staphylococcus or Escherichia coli is not antagonized by these anesthetics.View full abstractDownload PDF (532K) -
Synthesis of Thiazolidine Derivatives. (1)Yoshiyuki Takata1952 Volume 72 Issue 1 Pages 79-80
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSome thiazolidine derivatives were prepared by the introduction of p-aminobenzene-sulfonyl, p-nitrobenzenesulfonyl and p-nitrobenzoyl groups in the nuclear nitrogen of thiazolidine, thiazolidine sulfone and thiazolidine-4-carboxylic acid. Sulfonylation of the nuclear nitrogen in l-thiazolidine-4-carboxylic acid resulted, in most cases, in racemization.View full abstractDownload PDF (453K) -
Syntheses of Some Nitro Compounds as Synthetic Materials for Isoquinoline DerivativesTetsuji Kametani, Yasunori Masuda1952 Volume 72 Issue 1 Pages 81-85
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSeveral kinds of nitro compounds were prepared to obtain the amines necessary as the material for the synthesis of isoquinoline derivatives. Those prepared were α-methoxy-β-nitro-α, γ-diphenylpropane, β-methoxy-β-(3, 4-methylenedioxyphenyl)-α-piperonylidenenitroethane and α-acetamino-β-nitrodihydrosafrol.View full abstractDownload PDF (1062K) -
Synthesis of 1-Phenyl-3-veratryl-6, 7-dimethoxyisoquinolineTetsuji Kametani1952 Volume 72 Issue 1 Pages 85-87
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA new method of synthesizing isoquinoline derivatives possessing substituents in the 1-and 3-positions was devised and studies were made as to where the cyclization occurred in α-hydroxy-β-benzamido-α, γ-diveratrylpropane. The cyclization of the acid amide yielded some yellow powder which melted over a wide range but upon recrystallization, the substance melted at 184-185° which was thought to be 1-phenyl-3-veratryl-6, 7-dimethoxyisoquinoline. It was assumed that 1-phenyl-3-benzal-4-hydro-6, 7-dimethoxy-isoquinoline might have been formed by the migration of the double bond and examinations for such is being made.View full abstractDownload PDF (591K) -
Preparation of p-Aminophenyl Sulfone and Ether Derivatives, and their Antibacterial ActionMorizo Ishidate, Munemitsu Tomoeda, Hiroshi Ooya1952 Volume 72 Issue 1 Pages 88-91
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDerivatives of p-aminophenylalkyl sulfone, p-aminomethyl-phenylalkyl sulfone and p-aminophenylalkyl ether were prepared and their antibacterial activities in vitro against Mycobacterium tuberculosis (human strain), Staphylococcus aureus and Escherichia coli were studied (Table I). The toxicities on mice and competitive action on p-aminobenzoic acid of some of the chief derivatives were also examined (Tables II and III). Results obtained were as follows: 1) Among the alkyl sulf one and ether derivatives so far obtained, n-amyl and n-hexyl compounds showed the strongest activities against tubercle bacilli in Sauton's medium. It is interesting to note that all alkyl ethers gave the same results in Kirchner's medium.
2) In antibacterial activity, the alkyl ethers were superior to alkyl sulfones but the former showed a far stronger toxicity than the latter.
3) Alkyl sulf ones were found to be more or less antagonized in their activities against M. tuberculosis and Staph. aureus by the addition of p-aminobenzoic acid. Such competitive action was not observed in the case of alkyl ethers.View full abstractDownload PDF (861K) -
Synthesis of 1-[4′-, 1-[2′-and 1-[3′-(p-Aminobenzene-sulfonamido)-phenyl]-3-methyl-6, 7-methylenedioxyisoquinolineYasuo Morimoto1952 Volume 72 Issue 1 Pages 92-95
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAn acid amide (I) was obtained from α-methyl-β-methoxy-β-(3, 4-methylenedioxy-phenyl)-ethylamine with oo- and m-nitrobenzazide and p-nitrobenzoyl chloride, cyclized to a base (II) and reduced to the amine (III). This was led to its acetylsulfamine derivatives by p-acetaminobenzene sulfonyl chloride and saponified to 1-[4′, 1-[2′- and 1-[3′-(p-aminobenzenesulfonamido) -phenyl]-3-methyl-6, 7-methylenedioxyisoquinolines (V). This synthesis proceeded smoothly from (I) to (V). Attempt to obtain pytetra-hydroisoquinoline compounds (VI) by leading the free nitro base (II) to methylmethosulfate (VI) or methochloride (VI) with subsequent reduction met with strong resistance which was assumed to be due to the effect of the methyl group in the 3-position.View full abstractDownload PDF (739K) -
Synthesis of N-Methyl-1-[4′-, N-Methyl-1-[2′-and N-Methyl-1-[3′-(p-Aminobenzenesulfonamido)-phenyl]-3-methyl-1, 2, 3, 4-tetrahydroisoquinolineYasuo Morimoto1952 Volume 72 Issue 1 Pages 95-98
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to confirm the effect of the methyl radical in the 3-position of the compound (II) described in the previous report (cf. p. 92 of this issue), acid amides (I) were prepared from α-methyl-β-(3, 4-methylenedioxyphenyl)-ethylamine with p- and m-nitrobenzoyl chloride and o- and m-nitrobenzazide, and cyclized to the corresponding 3, 4-dihydro compounds (II). They were led to methylmethosulfates (III) or methochlorides (III) and catalytically reduced by which Py-tetrahydroisoquinoline compounds (IV) were easily obtained, the reduction proceeding smoothly. These amino compounds (IV) were acylated by p-acetaminobenzenesulfonyl chloride, and treated as in the previous report to N-methyl-1-[4′-, N-methyl-1-[2′- and N-methyl-1-[3′-(p-aminobenzenesulfonamido)-phenyl]-3-methyl-1, 2, 3, 4-tetrahydro isoquinol fines (VI). The acyl ation of Py-tetrahydroisoquinoline compounds (IV) with p-acetaminobenzene-sulfonyl chloride did not proceed smoothly, especially when the amino group was present in the 2′-position. This is probably due to the instability of the Py-tetrahydroisoquinoline ring against acylation.View full abstractDownload PDF (683K) -
The Reductive Ring Closure of Acyl-β-phenethylamidesYasuo Morimoto1952 Volume 72 Issue 1 Pages 99-101
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn the cyclization of aryl-β-phenethylamides (I), such as N-anisoyl-α-methyl-β-(3, 4-methylenedioxyphenyl)-ethylamide (I), m.p. 148-149°, by the Bischler-Napieralski-Perkin method, the use of stannous chloride by dissolving it in anhydrous dioxane in the presence of dry hydrochloric acid gas, addition of phosphoric oxychloride, and heating, with subsequent treatment of the product give a base which does not show a sharp melting point but gives positive Liebermann's reaction. Attempt to purify the base by fractional crystallization failed but adsorptive separation using active alumina column yielded a small amount of the objective 1-(P-methoxyphenyl)-3-methyl-6, 7-methylene-dioxytetrahydro-1, 2, 3, 4-isoquinol ine (IV), m.p. 95-96°, and a large amount of 1-(P-methoxyphenyl)-3-methyl-6, 7-methylenedioxy-3, 4-dihydroisoquinol me (II), m.p. 116-117°. The 1, 2-dihydro compound (IV) obtained by the catalytic reduction of (II) and (IV) were found to be identical by direct comparison.View full abstractDownload PDF (490K) -
The Isoquinoline Cyclization of Acyl-β-Phenethylamide Type Compounds in the Presence of Tin or ZincYasuo Morimoto1952 Volume 72 Issue 1 Pages 102-106
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn the cyclization of acyl-β-phenethylamides (I) by the Bischler-Napieralski-Perkin method in the presence of metallic tin or zinc, it has been found that the presence of these metals, especially that of tin, gave better yields and a high purity in the formation of 3, 4-dihydroisoquinolines (II). The solvent of hydrocarbons of benzene series used for cyclization was supplemented by dioxane, tetraline and decaline, and experiments were conducted with N-anisoyl-β- (3, 4-methylenedioxyphenyl) -α-methylethylamide (I) and various acid amides (I), with and without the use of tin. Without the use of tin, dioxane was found to be an excellent solvent, the yield of isoquinoline derivatives (II) being large and the purity high. On the other hand, in the presence of the metal, benzene was fund to give the best result. The use of tetraline or decaline results in a poor yield.View full abstractDownload PDF (805K) -
The Isoquinoline Cyclization of Acyl-β-methoxy-β-phenethylamide Type Compounds in the Presence of Tin or ZincYasuo Morimoto1952 Volume 72 Issue 1 Pages 106-110
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe use of corresponding β-methoxy derivatives (I) in place of the acid amides (I) as material for cyclization by the Bischler-Napieralski-Perkin method, also showed that the presence of a suitable amount of tin results in a larger yield and high purity of the product isoquinolines (III), similar to the case described in the previous report. The same results as described previously were found to be true as to the presence or absence of metals and the use of various solvents in the yield and purity of the products (III).View full abstractDownload PDF (649K) -
Sulfonamides Containing Thiocyano Group as Chemotherapeutic AgentsKichitaro Takatori, Kei Ose1952 Volume 72 Issue 1 Pages 111-116
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSChemotherapeutic values of the following were examined: p-Sulfanilamido-thiocyano-benzene (I), p-sulfanilamido-m-methylthiocyanobenzene (II), p-sulfanilamido-o-methyl-thiocyanobenzene (III), p-sulfanilamido-o-carbomethoxythiocyanobenzene (IV), p-sulfanilamido-o-carbethoxythiocyanobenzene (V), 2-sulfanilamido-6-methylbenzothiazole (VI) and p-sulfanilamido-iodobenzene (VII).
1) (I), (II), (III) and (VII) showed a powerful growth-inhibition in vitro against coccal bacteria, the action not being antagonized by p-aminobenzoic acid.
2) The toxicities of the acylated compounds of p-thiocyanoaniline were found to be different according to the kind of the acyl group present, the tolerable doze against mice being 2mg. in acetyl, 20mg. in benzoyl, and 30-50mg. in sulfanilyl compounds.
3) The sulfanomides of thiocyano series showed some promising results in therapeutic tests against induced pneumococcal infection in mice.View full abstractDownload PDF (896K) -
Synthesis of PhenylacetoneGenshun Sunagawa, Kichihei Okuda1952 Volume 72 Issue 1 Pages 117-118
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSMethyl phenyl ethylene glycol, m.p. 92-93°, was obtained in a good yield by the catalytic reduction of methyl. phenyl diketone in alcoholic solution at ordinary temperature and pressure, using platinum oxide as a catalyst. The same glycol is obtained as a by-product during formation of ephedrine from methyl phenyl diketone and methylamine by their catalytic reduction with platinum oxide catalyst. The treatment of this glycol with sulfuric acid results in pinacolin rearrangement to give phenylacetone in a good yield.View full abstractDownload PDF (333K) -
Genshun Sunagawa, Teishiro Kushima1952 Volume 72 Issue 1 Pages 119-120
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIt was found that thonzylamine undergoes decomposition easily by strong acids such as hydrochloric, sulfuric and nitric acids, but very little by phosphoric acid and not at all by boric, formic and acetic acids. It was also confirmed that the decomposition products of thonzylamine are dimethylaminoethylaminopyrimidine and p, p′-dimethoxydiphenylmethane.View full abstractDownload PDF (355K) -
Synthesis of Tetrahydrometathiazine DerivativesYoshiyuki Takata1952 Volume 72 Issue 1 Pages 120-121
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSTetrahydrometathiazine and its derivatives possessing p-aminobenzenesulfonyl, p-nitrobenzenesulfonyl and p-nitrobenzoyl groups substituted in the nuclear nitrogen were prepared.View full abstractDownload PDF (340K) -
The Antibacterial Properties of Compounds Containing the Tricarbonylmethane Group. VISadao Iguchi1952 Volume 72 Issue 1 Pages 122-127
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to examine the effect on antibacterial action of the presence or absence of a substituent in the benzene nucleus of 3-acyl-4-hydroxycoumarin, syntheses of the compounds possessing the hydroxyl at 7-position were attempted. One was the direct cyclization following condensation of β-resorcylic acid diacetate chloride and β-ketonic esters, and the other, the acylation by the application of aryl chlorides to 4, 7-dihydroxycoumarin in pyridine. It was assumed that the seat of attack on 4, 7-dihydroxy-coumarin by acylation would be the active methylene at 3-, enolic hydroxyl in the 4-and phenolic hydroxyl in the 7-positions. The reaction conditions were varied to observe the behavior of these active centers. The product obtained by acetyl chloride was 3-acetyl-4, 7-dihydroxycoumarin (B-type) and 3-acetyl-4-hydroxy-7-acetoxycou-marin (A-type), whose structures were determined from the results of ultraviolet absorption curves and by direct comparison with the synthetic substances obtained by direct cyclization.View full abstractDownload PDF (998K) -
The Antibacterial Properties of Compounds containing the Tricarbonyl-methane Group. VIBSadao Iguchi1952 Volume 72 Issue 1 Pages 128-131
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe acylation of 4, 7-dihydroxycoumarin by the use of butyryl, decanoyl and dodecanoyl chlorides in pyridine gave products different from the case of the use of acetyl chloride, the products being 4-hydroxy-7-acyloxy-coumarin (C-type) and 3-acyl-4-hydr-oxy-7-acyloxycoumarin (A-type). The objective compounds possessing acyl in the 3-position alone, i. e. 3-acyl-4, 7-dihydroxycoumarin (B-type), were obtained only after saponif ication of the A-type products. Consideration of the present and the previous reactions using acetyl chloride seems to point that under such conditions, the acylation of 4, 7-dihydroxycoumarin takes place first in the phenol is hydroxyl at 7-, followed by attack on the 3-position, the enolic hydroxyl at 4-position remaining indifferent to acylation.View full abstractDownload PDF (661K) -
The Antibacterial Properties of Compounds containing the Tricarbonyl-methane Group. VIISadao Iguchi1952 Volume 72 Issue 1 Pages 131-135
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFollowing previous experiments, 3-aryl-4-hydroxy-7-nitrocoumarin was synthesized by the direct cyclization following condensation of p-nitrosalicylic acid acetate chloride with β-ketonic esters in absolute ether. The compounds synthesized were 3-acetyl-, 3-butyryl and 3-decanoyl compounds which all showed similar ultraviolet absorption curves. The antibacterial action of these 7-nitro and 7-hydroxy compounds against Staphylococcus aureus and Escherichia coli was as follows:
1) Generally, the antibacterial action decreased with the introduction of a substituent as compared to that of non-substituted 3-acyl-4-hydroxycoumarin, the effect being greater in hydroxyl than in the nitro group.
2) In the presence of a substituent, the greater the aryl group substituted, the greater becomes the antibacterial action. The antibacterial action reaches the maximum with the decanoyl group in 7-hydroxy compounds.
3) When the acyl group in the 3-position of the 7-nitro compounds is small, i.e. in 3-acetyl compound, a slightly abnormal phenomenon is observed, the introduction of the nitro group heightening antibacterial action.
4) Of compounds substituted in the 7-position, 3-decanoyl-4-hydroxy-7-nitrocoumarin showed the strongest antibacterial action, being effective at 8, 000, 000 dilution against Staph. aureus.View full abstractDownload PDF (747K) -
On Fungus Cerehrin. (1)Takeshi Oda1952 Volume 72 Issue 1 Pages 136-139
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSTwo fungal cerebrins, hydroxycerebrin, C42H85O6N, and cerebrin, C42H85O5N, were isolated from the mycelium of surface-cultivated penicillin-producing mold, Q 176. Hydrolysis of hydroxycerebrin with 10% methanolic sulfuric acid gave α, β-dihydroxy-tetracosanoic acid and a base, C18H39O3N. The same treatment of cerebrin gave α-hydroxytetracosanoic acid (cerebroic acid) and the same base, C18H39O3N.View full abstractDownload PDF (788K) -
On Fungus Cerebrin. (2)Takeshi Oda1952 Volume 72 Issue 1 Pages 139-141
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSHydrolysis of crude cerebrin, obtained from the mycelium of penicillin-producing mold, Arima's pigmentless saltant, yielded cerebronic acid, lignoceric acid, and a base, C18H38O3N. Appearance of lignoceric acid suggests the existence of a new cerebrin. Oxidative cleavage of the base with chromic acid produced pentadecanoic acid.View full abstractDownload PDF (555K) -
On Fungus Cerebrin. (3)Takeshi Oda1952 Volume 72 Issue 1 Pages 142-145
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe chemical structure of the base, C18H39O3N, obtained by the hydrolysis of cerebrins, was confirmed to be CH3-(CH2)13-CHOH-CHOH-CHNH2-CH2OH, from the data obtained by the glycol cleavage of the N-benzoylated base.View full abstractDownload PDF (722K) -
Syntheses of 3-Amino- and 3-Aminomethyl-isoquinolinesMasao Ohara1952 Volume 72 Issue 1 Pages 145-147
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1-Methyl-3-amino-6, 7-methylenedioxyisoquinoline (IX) was prepared by the condensation of piperonal with acetylglycine, hydrogenation of the oxazolone (I), cyclization, dehydrogenation and Curtius reaction of methyl 1-methyl-6, 7-methylenedioxyisoquinoline-3-carboxylate (V). 3-Aminomethyl derivative (XII) was then obtained by the Mc-Fayden reaction of the hydrazide (VI) to the oxime (XI) followed by its catalytic hydrogenation with alcoholic hydrochloric acid. Physiological tests of (IX) and (XII) showed that the antispasmodic action of (IX) was approximately one-half of that of papaverine used as the control, and that such action was not found with (XII).View full abstractDownload PDF (554K) -
Reaction of Hydroxylamine Salt on Acetopropiodinitrile in the Presence of Fe++. (1)Hideo Kano1952 Volume 72 Issue 1 Pages 148-150
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe ordinary product of the aqueous solution of acetopropiodinitrile and hydroxyl-amine salt is 3, 4-dimethyl-5-aminoisoxazole but by the presence of a ferrous ion in this reaction, tetramethylpyrazine, 4, 5-dimethylimidazolone (2) and a basic substance, C10H16O2N4, of m.p. 210° (decomp.), were obtained besides the isoxazole. The hydrolysis of this base resulted in the liberation of carbon dioxide and ammonia to form tetra-methylpyrazine and 4, 5-dimethylimidazolone (2). Heating of the base with aniline or toluidine respectively gave diphenyl- or ditolyl-urea and. tetramethylpyrazine, while heating with benzyl or hexyl alcohol respectively yielded benzyl or hexyl-allophanate and tetramethylpyrazine.View full abstractDownload PDF (447K) -
Rearrangement of 5-Aminoisoxazoles. (1)Hideo Kano1952 Volume 72 Issue 1 Pages 150-152
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSHeating 3, 4-dimethyl-5-aminoisoxazole at around 180° results in intramolecular rearrangement to form its isomer, 4, 5-dimethylimidazolone (2). Presence of aniline or toluidine in this instance results in the partial formation of diphenyl- or ditolyl-urea. The same treatment of 3-methyl-4-ethyl- and 3-ethyl-4-methyl-5-aminoisoxazole yielded identical 4, 5-dimethylimidazolone (2) by intramolecular rearrangement.View full abstractDownload PDF (423K) -
Toshikazu Harada1952 Volume 72 Issue 1 Pages 153-154
Published: January 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (315K)