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Yasuji Ito, Noriko Takahashi
1954 Volume 74 Issue 4 Pages
325-328
Published: April 25, 1954
Released on J-STAGE: February 19, 2010
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Nomographs were made, one for obtaining the percentage of carbon and hydrogen in microanalyses from the amount of sample and the value of weight increase of absorption tubes, and the other for calculating the amount of nitrogen in the micro-Dumas method. Errors that might occur during these procedures were discussed briefly.
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Iwao Kawashiro
1954 Volume 74 Issue 4 Pages
328-330
Published: April 25, 1954
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Mono-
p-nitrophenylhydrazone, m.p. 157-158° (decomp.), was obtained from the periodate oxidation product of theophylline 7-glucoside. The hydrazone was found to decompose into glyoxal
p-nitrophenylosazone, free glyoxal, glyceraldehyde, and theophylline in acid solution, as in the case of the derivative obtained from methyl glucoside.
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Structure of N-Substituted Dithiourethanes. (4)
Shigeru Yoshida, Wataru Ishizuka
1954 Volume 74 Issue 4 Pages
331-335
Published: April 25, 1954
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Both S-phenacyl N-[2-methyl-4-aminopyrimidyl-(5)]-methyldithiocarbamate (VI) and S-phenacyl N-benzyldithiocarbamate (VII) lack the carbonyl absorption in their infrared spectra but S-phenacyl N-dimethyl (diethyl) dithiocarbamate (XII and XIII) show the carbonyl absorption at 5.92μ. Therefore, it may by concluded that (VI) and (VII) take the respective structures of 3-[2′-methyl-4′-aminopyrimidyl-(5)]-methyl-4-hydroxy-4-phenylthiothiazolidone-(2) and 3-benzyl-4-hydroxy-4-phenylthiothiazolidone-(2), and the formula (V) proposed earlier is corrected to (XV).
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Structure of N-Substituted Dithiourethanes. (5)
Shigeru Yoshida, Wataru Ishizuka
1954 Volume 74 Issue 4 Pages
335-339
Published: April 25, 1954
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The dithiocarbamate (III), synthesized from 2-methyl-4-amino-5-aminomethylpyrimidine (Ia) or benzylamine (Ib), α-haloketone (II), and carbon disulfide, and
o (
p)-methoxyphenyl-thiothiazolidone-(2) (XIX and XX) show the maximum absorption at 278mμ in the ultraviolet spectrum, and the thiothiazolone (V) obtained by the dehydration of (III) at 323mμ. Therefore, with the results of infrared absorption described in the previous paper, the structure of (III) should be (IV), and the dithiocarbamate synthesized from γ-aceto-γ-chloropropyl alcohol or its derivative is not (XXIV) or (XXV) but should be corrected to (XXVI). It follows that (XXVII) reported earlier would be 3-[2′-methyl-4′-aminopyrimidyl-(5′)]-methyl-3 a-methyltetrahydrofuro (2, 3-
d) thiazolothione-(2) (XVIII).
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Studies on Procaine Penicillin Crystal
Hiroshi Fujiwara
1954 Volume 74 Issue 4 Pages
339-343
Published: April 25, 1954
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Conditions for the formation of procaine-penicillin anhydride was clarified and revealed, from the X-ray photograph of the anhydride, that the crystals of procaine-penicillin were present as an anhydride and with one mole of the water of crystallization. Kinetic examination of thermal decomposition that occurs at the time of dehydration of procaine-penicillin indicated that the decomposition is affected by temperature and pressure.
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Kinetics of Decomposition of Procaine Penicillin in Aqueous Solutions
Hiroshi Fujiwara
1954 Volume 74 Issue 4 Pages
343-350
Published: April 25, 1954
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Decomposition velocity of procaine penicillin in aqueous solution was measured at various temperatures and pH. All showed primary reaction and the velocity was found to be the smallest at around pH 6.0. Absorption spectra during the decomposition were measured and it was assumed that procaine penicillin underwent decomposition to penicilloic acid above pH 6.0.
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Effect of Parotin on the Distribution of Radioactive P32 in vivo
Yosoji Ito, Susumu Tsurufuji, Yukio Kubota
1954 Volume 74 Issue 4 Pages
350-353
Published: April 25, 1954
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Inorganic phosphate labelled with P
32 was injected into groups of immature male albino rats which had been given parotin in various doses. Uptake of P
32 by incisor, femur, blood, liver, and adrenal gland of the rats was compared respectively with those of normal control animals by autopsy. The results obtained suggest following conclusions:
1) Soft tissues (blood, liver, and adrenal) of the parotin-administered rats take up less P
32 than the normal controls, though the differences were not always significant in the statistical test. On the other hand, hard tissues (incisor and femur) of the parotingroups generally take up more P
32.
2) Dosage of parotin, mode of the administration, period of the administration and killing, and many factors other than the effect of parotin influence the uptake of P
32 in animal tissues. It seems that the interference of these factors is responsible for the effect of parotin not being always statistically significant in the experiments. Some sources of a meaningless variations in the experimental data are discussed, the largest cause seemed to be that by individual difference.
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Aminocyclohexane Derivatives. (2)
Torizo Takahashi, Mikio Hori
1954 Volume 74 Issue 4 Pages
354-358
Published: April 25, 1954
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Grignard reagents were prepared by the usual method from allyl, propyl, and isopropyl bromide, and cyclohexyl chloride, and their respective application to 2-dimethylaminomethylcyclohexanone gave 1-allyl-, 1-propyl-, 1-isopropyl-, and 1-cyclo-hexyl-2-dimethylaminomethylcyclohexanols. Condensation of these aminoalcohols with various kinds of aromatic acid chlorides gave a series of esters. Catalytic reduction of such an ester,
p-nitrobenzoyloxy derivative, with palladium-carbon, gave
p-aminobenzoyloxy derivative. Of these esters, 1-ethyl- and 1-isopropyl-1-benzoyloxy-2-dimethylaminomethylcyclohexanes showed marked analgesic activity. Application of chloroacetyl chloride and α-bromopropionyl bromide to 1-ethyl- and 1-cyclohexyl derivatives of the foregoing hexanols, respectively, yielded haloacyloxy derivatives which were condensed with dimethyl- or diethylamine to give dialkylaminoacyloxy derivatives.
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Reaction of Monochlorodiphenyl Ether and Acetyl Chloride
Shoshichiro Kimoto, Kunihiro Asaki, Shuzo Kishi
1954 Volume 74 Issue 4 Pages
358-360
Published: April 25, 1954
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It was clarified that the application of acetyl chloride to 2-chloro-, 3-chloro-, or 4-chlorodiphenyl ether in the presence of aluminum chloride results in the introduction of the acetyl radical in the
para-position of the ether linkage (4′-position).
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Shichiro Akiya, Ryoji Sawamura
1954 Volume 74 Issue 4 Pages
360-363
Published: April 25, 1954
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1) Diacetone-D-galactose was oxidized with alkaline potassium permanganate, in accordance with the modification of Ohle and Berend, and D-galacturonic acid was obtained.
2) Good yield was obtained by the use of an excessive amount of oxidizing agent and decomposing the unreacted permanganate with hydrogen peroxide, irrespective of the purity of the raw material.
3) In liberating uronic acid by the removal of barium from barium D-galacturonate, the reaction time was shortened and good yield obtained by the gradual addition of the corresponding amount of 0.2
N sulfuric acid and by the stepwise addition of alcohol.
4) Attempt to isolate and purify galacturonic acid by the ion exchange resin, without once precipitating the barium salt, was not successful. It is thought that purification of galacturonic acid as its barium salt is of important significance in making crystallization of the acid possible and in obtaining higher purity.
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Tatsuo Kariyone, Takao Matsuno
1954 Volume 74 Issue 4 Pages
363-365
Published: April 25, 1954
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Distribution of glycosides in the rind of Citrus fruits was examined. Hesperidin was detected in
Citrus Tachibana Tanaka, C. Junos Sieb. ex Tanaka, C. Iyo Hort. ex Tanaka, and C. Sudachi Hort. ex Shirai, and naringin from C. medioglobosa Hort. ex Tanaka, and C. Hassaku Hort. ex Tanaka. The content of hesperidin was as much as 15% in the young fruit of C. Tachibana. Poncirin (=kikokunetin-7-glucorhamnoside), obtained from the flower petals of Poncirus trifoliata Rafin. by Dr. Hattori, was detected from the fruit of this plant. Sosa and Sanie obtained a flavanone glycoside from Citrus trifoliata L. (alias Poncirus trifoliata) and designated this as a new substance, citrifolioside, but the properties and molecular formula given by them are identical with those of poncirin. It is, therefore, proposed that the name of citrifolioside be withdrawn.
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Syntheses of Some Derivatives of Limonin
Atsushi Fujita, Yoshio Hirose
1954 Volume 74 Issue 4 Pages
365-367
Published: April 25, 1954
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Two new derivatives of limonin have been obtained. One is dihydrolimonin, C
26H
32O
8, m.p. 273-274°, [α]
D25: +25°, obtained by the reduction of limonin with amalgamated sodium, and the other, dehydrolimonin, C
26H
28O
8, m.p. 312°, [α]
D25: -133.6°, by oxidation with iodine. Limonin also gives an ordinary oxime, m.p. 255°. Although limonin, dihydrolimonin, and dehydrolimonin give positive Molisch reaction, Emerson's limonilic and dehydrolimoninic acid give negative reaction, showing that they no longer possess the furan nucleus in their molecules.
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Thioether-type Thiamine Derivatives
Kenzo Sirakawa
1954 Volume 74 Issue 4 Pages
367-369
Published: April 25, 1954
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By the respective application of ethylene chlorhydrin, monochloroacetic acid, bromoacetone, and
p-nitrophenacyl bromide on the sodium salt of thiol-type vitamin B
1 or thiol-type O-benzoyl vitamin B
1, five kinds of thioether-type derivatives were obtained. None of these showed vitamin B
1-activity in preventing B
1-deficiency in
Urolonca domestica. S-Carbethoxy compound obtained by the application of ethyl chlorocarbonate to the sodium salt of thiol-type O-benzoyl vitamin B
1 showed a slight B
1 activity.
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Synthesis of Some 2-Thiazolylhydrazones and their Antibacterial Activity on Mycobacterium tuberculosis
Hyozo Taniyama, Yukio Tanaka, Homare Uchida
1954 Volume 74 Issue 4 Pages
370-373
Published: April 25, 1954
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Thiosemicarbazones of benzaldehyde, salicylaldehyde,
p-acetaminobenzaldehyde,
p-methoxybenzaldehyde,
p-ethylsulfonylbenzaldehyde, cinnamaldehyde, α-amylcinnamaldehyde, and
o-hydroxyacetophenone were condensed with chloroacetone and α, β-dichloroethyl acetate and 4-methyl-2-thiazolylhydrazones were chiefly obtained from the former and 2-thiazolylhydrazones from the latter reaction. Antitubercular action
in vitro of these thiazole compounds were found to be inferior to the thiosemicarbazones (TB 1, TB 2, TB 3) of the aldehydes prior to thiazole-cyclization. However, 2-salicylidenehydrazinothiazole alone was contrary to the case and showed a marked growth inhibiting action against tubercle bacilli.
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Synthesis of Some 2-(p-Aminobenzenesulfonyl)-hydrazono-4-thiazolidones and their Antibacterial Activity on Mycobacterium tuberculosis
Hyozo Taniyama, Bonpei Yasui, Homare Uchida
1954 Volume 74 Issue 4 Pages
374-379
Published: April 25, 1954
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2-(
p-Aminobenzenesulfonyl)-hydrazone-4-thiazolidone hydrochloride (I) and its 5-methyl (II), 5-dimethyl (III), and 5-carboxyl (IV) derivatives were prepared in order to examine their growth inhibition of tubercle bacilli
in vitro. The 5-methyl and 5-ethyl compounds, especially (III), were stronger than (I) in inhibiting growth. 2-(
p-Aminobenzenesulfonyl)-imino-4-thiazolidone hydrochloride, possessing similar structure as (I), was found to be inferior in antibacterial action than (I) from which it was found that =N⋅NH
2 group in 2-position was a functional group which possessed the effect of increasing such activity, as compared to =NH group. The antibacterial activity entirely disappears on changing the NH
2 in
para-position of the benzene nucleus to CH
3CONH in (I), (II), and (III).
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Constituents of Ko-jô-kon (Polygonum cuspidatum Sieb. et Zucc.)
Kiyoshi Tsukida, Michiko Yoneshige
1954 Volume 74 Issue 4 Pages
379-382
Published: April 25, 1954
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Dried root of
Polygonum cuspidatum was consecutively extracted with ethanol and ether, transited to the alkaline solution, and submitted to liquid chromatography by which hydroxyanthraquinones were isolated. By repeated purification through vacuum sublimation and recrystallization, each was identified by zinc distillation, acetylation, or one-dimentional paper chromatography. Besides hydroxyanthraquinones, such as emodin, emodin monomethyl ether, and chrysophanic acid, some reddish brown amorphous powder of m.p. 280° (decomp.) was obtained and glucose and rhamnose were identified as their osazones. The total amount of hydroxyanthraquinoes was 0.1-0.5% of the dried root.
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Constituents of Japanese Rhubarb (Rheum undulatum L.)
Kiyoshi Tsukida, Michiko Yoneshige, Junko Tsujioka
1954 Volume 74 Issue 4 Pages
382-385
Published: April 25, 1954
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Dried root of
Rheum undulatum was consecutively extracted with ethanol and ether, and by transition to alkaline solution, hydroxyanthraquinones, such as chrysophanic acid, emodin, and aloe-emodin, and rhapontin were obtained besides unknown crystals, oily substance, and resins. Rhein and emodin monomethyl ether were detected during the isolation process but they were not obtained as crystals. Confirmation of hydroxyanthraquinones was made by the same procedures as in the case of
Polygonum cuspidatum.
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Components of Rumex Andreaeanum Mak
Kiyoshi Tsukida
1954 Volume 74 Issue 4 Pages
386-388
Published: April 25, 1954
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Dried root of
Rheum andreaeanum (three years after collection) was consecutively extracted with petroleum benzine, ethanol, benzene, and ether, treated with cold or hot alkali, and chrysophanic acid, emodin, and rhein were isolated and confirmed. A substance similar to rhein anthrone was detected during this isolation procedures but it could not be obtained in crystaliine form. Glucose was isolated as its osazone by the usual method.
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Paper Chromatography of Hydroxyanthraquinones (Addendum)
Kiyoshi Tsukida
1954 Volume 74 Issue 4 Pages
388-394
Published: April 25, 1954
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The detection of hydroxyanthraquinones by paper chromatography, described in the first report of this series, was further examined on its reliability by carrying it out with benzene, toluene, or cyclohexane as the transition phase and water, alcohols, or polyhydric alcohols as the fixation phase. In the majority of cases, isolation and detection of hydroxyanthraquinones were found to be possible and a close relation was found to exist between their structures and Rf values. This method was proved to be an influential means in assuming relative position of the hydroxyl groups in unknown hydroxyanthraquinone derivatives. Further, a simple new method was devised for detecting such compounds within 30minutes with water-saturated toluene as the developer and this was utilized in examining the distribution of hydroxyanthraquinones in Japanese rhubarb,
Rumex Andreaeanum Makino, and
Polygonum cuspidatum. Sieb. et Zucc.
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Constituents of Yô-tei-kon (Rumex japonicus Meisn.)
Kiyoshi Tsukida
1954 Volume 74 Issue 4 Pages
394-397
Published: April 25, 1954
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The dried root of
Rumex japonicus Meisn. was extracted with benzene, transited to an alkaline solution, and chrysophanic acid, emodin, and several kinds of unknown substances were obtained. The fresh root of this plant was extracted consecutively with chloroform and benzene, shaken with potassium hydroxide in hydrogen stream, and benzene layer was separated. Benzene residue was treated with chloroform and submitted to chromatopile method from which chrysophanic acid anthrone was isolated and proved as the 9-anthrone compound.
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Components of the Fruit of Phamnus dahurica Pall. var. nipponica Mak
Kiyoshi Tsukida
1954 Volume 74 Issue 4 Pages
398-400
Published: April 25, 1954
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Fresh fruit of Rhamnus dahurica var. nipponica was consecutively extracted with chloroform and benzene, shaken with potassium hydroxide in hydrogen stream, and the benzene layer was separated. The benzene residue was treated with chloroform and isolation by the chromatopile method was attempted as in the case of Rumex japonicus. Emodin anthrone isolated there from was identified as the 9-anthrone compound. Chrysophanic acid, chrysophanic acid anthrone, emodin, and five unknown substances were detectedduring the course of this isolation. Glucose was isolated as the sugar and confirmed ad its osazone.
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Components of the Bark of Rhamnus crenata Miq
Kiyoshi Tsukida
1954 Volume 74 Issue 4 Pages
401-404
Published: April 25, 1954
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Fresh bark of
Rhamnus crenata Miq. was consecutively extracted with benzene and chloroform, treated with potassium hydroxide in hydrogen stream, and the chloroform-soluble portion was submitted to column chromatography with calcium carbonate and zinc carbonate as the adsorption agent and petroleum benzine, chloroform containing 5-10% ethanol, methanol-saturated cyclohexane, cyclohexane, or chloroform: ethanol: benzene (19:1:5) mixture as the developer. Chrysophanic acid, chrysophanic acid anthrone, and emodin were isolated, and emodin anthrone and others were detected.
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Haruo Saikachi, Haruhiko Hoshida
1954 Volume 74 Issue 4 Pages
404-408
Published: April 25, 1954
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β-2-(5-Nitro)-furylserine ethyl ester hydrochloride (I), m.p. 175° (decomp.), was prepared by the condensation of 2-(5-nitro)-furfural and glycine ethyl ester, via the intermediate Schiff base. From existing literature and experimental evidences, this substance was assumed to be the DL-compound of
erythro-configuration. (I) was respectively condensed with acetyl chloride, benzoyl chloride,
p-nitrobenzoyl chloride,
p-chlorobenzoyl chloride (b.p
18 115°), 2, 4-dichlorobenzoyl chloride (b.p
34 158°), cinnamoyl chloride (m.p. 35-36°), furoyl chloride (m.p. -2°), 2-(5-nitro)-furoyl chloride (m.p. 34°), furylacryloyl chloride (b.p
6 106.5°), and 2-(5-nitro)-furylacryloyl chloride (m.p. 99°). The N-acylated
erythro-DL-β-[2-(-nitro)-furyl]-serine ethyl esters thereby obtained were as follows: N-acetyl-, m.p. 89°; N-benzoyl-, m.p. 115-117°; N-(
p-nitrobenzoyl)-, m.p. 96-97°; N-(
p-chlorobenzoyl)-, m.p. 85-86°; N-(2, 4-dichlorobenzoyl)- (or 1-(2, 4-dichlorobenzoylamido)-2-[2-(5-nitro)-furyl]-ethylene), m.p. 229°; N-cinnamoyl-, m.p. 114-115°; N-furoyl-, m.p. 122°; N-[2-(5-nitro)-furoyl]-, m.p. 141°; N-furylacryloyl-, m.p. 188°; N-[2-(5-nitro)-furylacryloyl]-, m.p. 189°.
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Zen-ichi Horii, Ken-ichi Sakurai, Koichi Tomino
1954 Volume 74 Issue 4 Pages
408-409
Published: April 25, 1954
Released on J-STAGE: February 19, 2010
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Since the existing methods of the synthetic preparation of urocanic acid were not so satisfactory, a more convenient method, readily adaptable to the large scale preparation of urocanic acid, was developed. This new route consists of the oxidation of imidazole carbinol to imidazole aldehyde with aqueous potassium persulfate solution followed by condensation with malonic acid in the presence of pyridine. Urocanic acid obtained by this method gives the identical melting point and ultraviolet absorption spectrum as those of the acid prepared by enzymatic process.
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Qualitative and Quantitative Analysis of Perillaldehyde Oxime, 5-Nitrofurfural Semicarbazone, and p-Acetaminobenzaldehyde Thiosemicarbazone
Kakuma Nagasawa, Seiichi Ohkuma
1954 Volume 74 Issue 4 Pages
410-413
Published: April 25, 1954
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Corresponding aldehyde 2, 4-dinitrophenylhydrazones are formed by the application of 2, 4-dinitrophenylhydrazine to perillaldehyde oxime (I), 5-nitrofurfural semicarbazone (II), and
p-acetaminobenzaldehyde thiosemicarbazone (III), liberating hydroxylamine, semicarbazide, or thiosemicarbazide. The acetonic solution of the hydrazones gives red coloration in (I) and (III) and blue coloration in (II) with potassium hydroxide. The detection of hydroxylamine was made by the diazo reaction with nitric acid, and that of thiosemicarbazide with sodium pentacyanoamminferroate or the Grote's reagent. The average formation rate of the 2, 4-dinitrophenylhydrazones of (I), (II), and (III) were 99.7%, 99.6%, and 98.3%, respectively, showing that they can be utilized for gravimetric analyses.
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Synthesis of Amines by Reduction of Oximes
Tetsuji Kametani, Yukio Nomura
1954 Volume 74 Issue 4 Pages
413-416
Published: April 25, 1954
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Synthesis of amines was attempted by the reduction of nitrogenous compounds, such as oximes, by the utilization of hydrogen which is generated when Raney nickel is developed in alkaline solution. The oxime and aqueous alkali were placed in a flask provided with fractionation column, dropping funnel, and cooler for steam distillation. Raney nickel was added to this mixture in one lot, allowed to react in the cold, and water added from the funnel when the reaction became mild. Steam distillation of this mixture gave pure amine in a short time. Reduction of nitriles was also successful by this method but details of this will be reported after further examination. The compounds obtained from corresponding oximes were as follows: Benzylamine, 3, 4-dimethoxybenzylamine, 3, 4-methylenedioxybenzylamine, α-phenethylamine, β-amino-α, γ-diphenylpropane, benzhydrylamine, and cyclohexylamine.
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Synthesis of Papaverine Derivatives. (5)
Tetsuji Kametani, Mizuho Inagaki
1954 Volume 74 Issue 4 Pages
417-419
Published: April 25, 1954
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Allied compounds of papaverine possessing a sulfur-containing substituent in 1-position are comparatively few. Considering the marked analgesic action of thiophene derivatives known recently, such compounds possessing thiophene nucleus in 1-position of isoquinoline derivatives seemed of interest as to their physiological activity. Following three compounds were prepared from ordinarily used amines and α-thiophenecarboxylic acid: 1-(2′-Thienyl)-3-methyl-6, 7-methylenedioxyisoquinoline (I), 1-(2′-thienyl)-3-methyl-6, 7-methylenedioxy-3, 4-dihydroisoquinoline (II), and 1-(2′-thienyl)-6, 7-dimethoxy-3, 4-dihydroisoquinoline (III). Of these, (I) showed approximately one-fifth the analgesic action of 3-dimethylamino-1, 1-di (2′-thienyl) butene-1. The papaverine-like action of these compounds are being examined.
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Syntheses of Xanthine from 4-Iminovioluric acid
Morizo Ishidate, Minoru Sekiya, Ichiro Kurita
1954 Volume 74 Issue 4 Pages
420-421
Published: April 25, 1954
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Heating 4-iminovioluric acid with formamide gives a very impure xanthine, the yield being 35% of the theory at the maximum. The yield can be increased to around 50% by carrying out the reaction in the presence of a small amount of a sulfide or iron powder. Xanthine can be obtained in 65-70% yield by the reduction of 4-iminovioluric acid in formamide with hydrogen sulfide or ammonium sulfide, or by its catalytic reduction with hydrogen at high pressure.
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Shun Iseda, Kazuyoshi Yagishita, Naoshi Toya
1954 Volume 74 Issue 4 Pages
422-423
Published: April 25, 1954
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The unsaponifiable matter of the ether-soluble fraction of the trunk bark of
Ilex integra Thunb. yielded α-and β-amyrins, lupeol, and ilexol. β-Amyrin had also been found in white bird-lime, and α-and β-amyrins and ilexol had been obtained from green bird-lime similar to white bird-lime, described in the first paper of this series. In other words, α-amyrin composes the chief constituent in the former and β-amyrin in the latter, from which sitosterol was also obtained.
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Makoto Unoki, Yugi Katori
1954 Volume 74 Issue 4 Pages
423-425
Published: April 25, 1954
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3-(2′-Methyl-4′-amino-5′-pyrimidyl)-methyl-4-methyl-5-β-hydroxyethyl-2-thiothia-zolone was treated with a slightly concentrated hydrogen peroxide, and the sulfate solution of vitamin B
1 sulfate thereby obtained was neutralized with sodium bicarbonate after the addition of nitric acid or sodium nitrate from which vitamin B
1 mononitrate was obtained in a pure state and in a good yield. The same treatment of the O-acyl derivatives in place of the foregoing thiothiazolone compound gave several kinds of acylvitamin B
1 mononitrate.
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Synthesis of 10, 11-Dihydrodibenz (b, f) oxepin-10 (11 H)-one
Shoshichiro Kimoto, Kimihiko Kimura, Shinsuke Muramatsu
1954 Volume 74 Issue 4 Pages
426-427
Published: April 25, 1954
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2-Phenoxyphenylacetic acid, m.p. 91°, was obtained in a good yield from 2-acetyl-diphenyl ether, b.p
3 132-138°, by the Willgerodt-Kindler reaction. Cyclization of the acid gave 10, 11-dihydrodibenz (b, f) oxepin-10 (11 H)-one, m.p. 55-56°.
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Isolation of Individual Alkaloids
Mitsuya Tanaka, Tomiko Kimura
1954 Volume 74 Issue 4 Pages
427-430
Published: April 25, 1954
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Alkaloidal components of domestic rye ergot (from Iwate Pref.) were studied and ergocristinine, ergocristine, and minute amounts of ergotaminine and ergometrine were isolated. Ergotaminine was not always isolated and its yield seemed to vary with the strain of the fungus, host plant, and the method of extraction. An ergotaminine-like alkaloid of m.p. 225° (decomp.) was always obtained from the phenolic portion (ergosinine fraction) and the constituent amino acids obtained were proline and phenylalanine, as well as alanine and β-alanine (?). The water-soluble alkaloid fraction indicated the presence of a base which gave no fluorescence under ultraviolet light and gave red coloration with the Ehrlich reagent, with ultraviolet absorption maximum at 2750 Å. Studies on this substance are expected to be made at a later date.
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Studies on Ergot Alkaloids by Paper Chromatography
Mitsuya Tanaka, Tomiko Kimura
1954 Volume 74 Issue 4 Pages
430-433
Published: April 25, 1954
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Paper chromatography of ergot alkaloids was examined. Mutual separation of peptide-type alkaloids by two-dimensional paper chromatography with 1%
d-tartaric acid-water and acetic acid-butanol as the developer was attempted and some good results were obtained. Paper chromatography was carried out on the decomposition products (amino acids and α-keto acids) of the alkaloids to examine foregoing chromatographic method. Ergot from domestic rye (Rokuhara, Iwate Pref.) was studied by paper chromatography.
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