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Volume 75, Issue 2
Displaying 1-37 of 37 articles from this issue
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Furan Compounds. (1)Hidetaka Uoda, Akira Takai, Toshiko Yokoi1955 Volume 75 Issue 2 Pages 117-120
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFurfural, furylacrolein, and their 5-nitro derivatives were applied respectively to ethyl N1-carbaminylhydrazinoacetate and N1-thiocarbaminylacetate, and the straight-chain azomethine compounds thereby formed were cyclized by heating with dilute mineral acids to prepare cyclic azomethine compounds possessing a furan ring. These compounds were also obtained by the application of the foregoing aldehydes to mineral acid solution of 1-aminohydantoin and 1-amino-2-thiohydantoin. Antibacterial tests revealed that the compounds possessing a nitro group had excellent actions, either in the straight-chain or cyclic forms.View full abstractDownload PDF (827K) -
Reaction of Pyridine 1-Oxide, Qunoline 1-Oxide, and Dimethylaniline 1-Oxide with Phosphorus TrichlorideMasatomo Hamana1955 Volume 75 Issue 2 Pages 121-123
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAddition of phosphorus trichloride to the chloroform or ethyl acetate solution of pyridine or quinoline 1-oxide results in immediate exothermic reaction and desoxidation occurs. Use of ether as the solvent results in the recovery of over 20% of the starting material which is insoluble in this solvent. The yield of the desoxidation product is also poor when dimethylformamide is used as the solvent, probably because of the occurrence of some side reactions. This desoxidation reaction is one-sided and the 2-chloro, 4-chloro, or 2-hydroxy compound is not obtained. This reaction, however, is not specific to aromatic heterocyclic amine oxides and can be applied to aliphatic tertiary amine oxides, dimethylaniline N-oxide being desoxidated by phosphorus trichloride to dimethylaniline.View full abstractDownload PDF (478K) -
Reaction of 4-Nitropyridine 1-Oxide with Phosphorus TrichlorideMasatomo Hamana1955 Volume 75 Issue 2 Pages 123-126
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe reaction of 4-nitropyridine 1-oxide and phosphorus trichloride proceeds in the following order: O2N- N→O+PCl3(A)→O2N- N+POCl3(B)→Cl- N+O= N- N
What effect the kind of solvent used and reaction temperature had on the side-reaction (B) was examined and following results were obtained:
1) Ethyl acetate and chloroform are suitable as the reaction solvent and carbon disulfide and dioxane are unsuitable.
2) In general, reaction carried out in the cold resulted in the recovery of the starting material, indicating the necessity of warming at a definite temperature for the completion of the reaction.
3) Heating at a higher temperature or lengthening of the reaction period tends to cause greater occurrence of the (B) reaction. The formation of N-(4′-pyridyl)-4-pyridone is marked in carbon tetrachloride.
Application of aniline hydrochloride or 10% hydrochloric acid to N-(4′-pyridyl)-4-pyridone results in the formation of two moles of pyridine derivatives but the application of 10% sodium hydroxide causes partial cleavage of the pyridine ring. There is no reaction with 28% ammonia water or water.View full abstractDownload PDF (588K) -
Reaction of 4-Nitroquinoline 1-Oxide with Phosphorus TrichlorideMasatomo Hamana1955 Volume 75 Issue 2 Pages 127-130
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) The reactivity of the 1-oxide group in 4-nitroquinoline 1-oxide against phosphorus trichloride is smaller than that of quinoline 1-oxide.
2) In this case, the reactivity of the 4-nitro group is larger and the reaction proceeds in the A and B directions (cf. (IV-2)).
The reaction (A) hardly occurs in the ethyl acetate solvent and only (B) reaction alone seems to occur.
3) The reactivity of the 4-nitro group in 4-nitroquinoline 1-oxide is far greater than that in 4-nitropyridine 1-oxide.
4) Chloroform and ethyl acetate are suitable as the reaction solvent and carbon tetrachloride is unsuitable.View full abstractDownload PDF (695K) -
Reaction of 4-Substituted Pyridine and Quinoline 1-Oxides having an Active Hydrogen with Phosphorus TrichlorideMasatomo Hamana1955 Volume 75 Issue 2 Pages 130-134
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) 4-Hydroxy- and 4-amino-pyridine or -quinoline 1-oxide are desoxidated by phosphorus trichloride but the yield is generally poor.
2) In either case, reaction with their acetates gives a better yield. The 4-hydroxy compound yields the 4-hydroxy product but 4-amino compound yields invariably 4-acetamino compound.
3) The reaction of 4-hydroxyquinoline 1-oxide sometimes yields 4-chloroquinoline as a by-product but not 4-hydroxypyridine. This fact suggests that the reactivity of the 4-hydroxy group in quinoline derivatives is greater than that in pyridine derivatives.
4) 4-Ethoxyquinoline 1-oxide undergoes facile desoxidation by the action of phosphorus trichloride to form 4-ethoxyquinoline in a good yield.View full abstractDownload PDF (912K) -
Desoxidation of Aromatic Tertiary Amine Oxides by Phosphorus TribromideMasatomo Hamana1955 Volume 75 Issue 2 Pages 135-138
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) Phosphorus tribromide effects desoxidation of aromatic amine oxides, similar to the action of phosphorus trichloride, but its reactivity is weaker.
2) The side reaction occurs also in the similar manner but a marked difference is observed in the action of phosphorus tribromide on 4-nitroquinoline 1-oxide in which the action occurs preferentially with the 1-oxide group than the 4-nitro group and the reaction proceeds in the following sequence.
3) The yield of the desoxidation product is very poor from 4-amino-pyridine and -quinoline 1-oxides and this is a marked difference from that of their reaction with phosphorus trichloride or that of 4-hydroxy compound.View full abstractDownload PDF (724K) -
Desoxidation of Aromatic Tertiary Amine Oxides by Triphenyl PhosphiteMasatomo Hamana1955 Volume 75 Issue 2 Pages 139-145
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) Triphenyl phosphite also effects desoxidation of amine oxides of pyridine series, similar to the action of phosphorus tribromide or trichloride, but its desoxidative power is far smaller.
2) This difference is especially marked in the case of the 4-nitro group from which no desoxidation product is obtained. On the other hand, a comparatively good yield is obtained in the case of the 4-amino compound, which is in sharp contrast with the poor yield from this compound by phosphorus tribromide.
3) The reaction product from quinoline 1-oxide and triphenyl phosphite was examined and the following course of reaction was confirmed by the isolation of triphenyl phosphate.
4) The desoxidation reaction of the amine oxides of the pyridine series by phosphorus trichloride, phosphorus tribromide, and triphenyl phosphite was compared and summarized, and considerations were made of the reaction course, reaction mechanism, and side-reactions.View full abstractDownload PDF (1014K) -
Influence of Inorganic Salts and Vitamin on the Formation of AmylaseYasushi Mihashi, Masako Tatsumi1955 Volume 75 Issue 2 Pages 146-149
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAspergillus orysae was cultured at 30° for 10 days in a modified Czapek-Dox medium containing a minute amount of inorganic salt (NaCl, LiCl, CaCl2, SrCl2, ZnCl2, AlCl3, MnCl2, NiCl2, CoCl2, KI, KBr, KF, or KSCN), and vitamins (B1, B2, B6, nicotinic acid, nicotinamide, pteroylglutamic acid, 2-methyl-1, 4-naphthoquinone, C, or p-aminobenzoic acid. Sodium chloride and vitamin C, especially p-aminobenzoic acid, were found to be effective in increased production of yeast amylase.View full abstractDownload PDF (417K) -
Influence of p-Aminobenzoic Acid and its Related Compounds on the Formation of AmylaseYasushi Mihashi, Masako Tatsumi1955 Volume 75 Issue 2 Pages 149-151
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSWhen Aspergillus orysae is cultured in a medium containing 0.15-3.0mg. of p-aminobenzoic acid per 50cc. of the medium, the production of amylase was found to increase the most. The same experiments were carried out with compounds structurally related to p-aminobenzoic acid, such as o- and m-aminobenzoic, p-nitrobenzoic, and sulfanilic acids, and a few derivatives of p-aminobenzoic acid, but no better result was obtained.View full abstractDownload PDF (335K) -
Improvement of the Method Supplying Carbon Dioxide for Micro-Dumas Nitrogen DeterminationMinoru Fukuda1955 Volume 75 Issue 2 Pages 151-153
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSEvolution of carbon dioxide by the pyrolysis of sodium hydrogen carbonate may advantageously be used for the nitrogen analysis by the micro-Dumas method but the procedure is attended with some defects in that the control of the carbon dioxide stream is difficult and that the life of sodium hydrogen carbonate is very short. The first of such defects was overcome by devising a kind of pressure regulating stopcock which would freely control the carbon dioxide stream, while automatically maintaining the combustion tube at a constant pressure. The second point was somewhat overcome by the devise of a simple carbon dioxide generator. By the use of this generator, about 45g. of sodium hydrogen carbonate is taken and allows continued use for over nine hours.View full abstractDownload PDF (425K) -
Syntheses of Ethylenediamine, Ethanolamine, Trimethylenediamine, and Propanolamine DerivativesKyuji Abe1955 Volume 75 Issue 2 Pages 153-159
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) N-β-Bromoethylsaccharin and α, β-disaccharinoethane were prepared from saccharin and ethylene dibromide, and converted advantageously to RNHCH2CH2NHR, RNHCH2CH2NH2, RNHCH2CH2OH, and RNHCH2CH2OC6H5 by the process shown in Table I.
2) The same procedures as above, using trimethylene dibromide, yielded RNHCH2CH2CH2NHR, RNHCH2CH2CH2NH2, RNHCH2CH2CH2OH, and RNHCH2CH2CH2OC6H5.
3) Non-symmetric alkylethylenediamines were prepared by the chlorination of RNHCH2CH2OH to RNHCH2CH2Cl, with subsequent application of an amine.
4) Potassium saccharin and ethylene dibromide undergo condensation after being heated at above 200° for a long period of time and the formation of a large amount of disaccharinoethane as a by-product cannot be avoided. The use of dimethylformamide as a solvent in this case yielded N-β-bromoethylsaccharin in 90% yield on being heated on a boiling water bath.View full abstractDownload PDF (932K) -
Syntheses of Aliphatic Secondary AminesKyuji Abe1955 Volume 75 Issue 2 Pages 159-164
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) Since saccharin does not react with alkyl halides under an ordinary pressure, alkylsaccharin has been prepared by reacting under high pressure and temperature. The condensation was successfully concluded at an ordinary pressure by the use of dimethylformamide as a solvent. By the use of this procedure, aliphatic secondary amines possessing a long, straight-chain alkyls (CnH2n+1, n=1-12) and branched-chain alkyls (isopropyl, isobutyl, and sec-butyl) were prepared in a good yield.
2) In the case of isopropyl and sec-butyl groups, the product, N-alkylsaccharin, was accompanied with its isomer, O-alkylsaccharin, but the two isomers were separable by the difference of their solubility in ethanol. The isomers can also be separated in the subsequent alkaline hydrolysis.
3) The final hydrolysis procedure was found to be the easiest in the methyl group, becoming increasingly difficult with the increase in the number of carbon atoms in the alkyl chain. When the number of carbon atoms is the same, the hydrolysis is more difficult in the branched-chain alkyl than the straight-chain.View full abstractDownload PDF (711K) -
Synthesis of β-Methylamino-α-phenylpropane and γ-Methylamino-α-phenylbutaneKyuji Abe1955 Volume 75 Issue 2 Pages 164-167
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSα-Methylphenethyl and α-methylphenylpropyl bromides or tosylates easily undergo decomposition but will undergo condensation with saccharin when dimethylformamide is used as a solvent. By the successful conclusion of this first step, preparation of β-methylamino-α-phenylpropane and γ-methylamino-α-phenylbutane by the saccharin method became possible. The final process of acid hydrolysis can be effected by boiling with conc. hydrochloric acid under an ordinary pressure but the reaction is more sluggish than in the case of a straight chain phenethyl group.View full abstractDownload PDF (534K) -
Mechanism of the Saccharin MethodKyuji Abe1955 Volume 75 Issue 2 Pages 168-171
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe characteristics of the saccharin method is that the final step of acid hydrolysis proceeds in marked easiness. The presence of a carboxyl in the ortho-position makes it extremely facile, compared to the aryl sulfonamide process, and the reason for it is assumed to be as follows: i) Electron density of the sulfur atom decreases by the +E effect and ortho effect of the positive carboxyl group, making it more easily attacked by the water molecule; ii) the presence of a hydroxyl in the molecule has increased its solubility in water.View full abstractDownload PDF (571K) -
Organic Acids in the Leaves of Catalpa ovate G. Don. and Catalpa bignonioides WaltTashichiro Nakaoki, Naokata Morita1955 Volume 75 Issue 2 Pages 171-172
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIt has been clarified that the seeds of Catalpa ovata G. Don. contain p-hydroxybenzoic acid but there is no report as to the component of its leaves. Having heard that the said leaves were effective for the athlete's foot, examinations were made of the leaves of Catalpa ovata and C. bignonioides Walt. p-Hydroxybenzoic acid was obtained in 2% yield from the former while p-hydroxycinnamic acid was obtained in 1.5% yield from the latter. These organic acids were assumed to be present as their alkali salts. The distinction of these two species are difficult from outward appearance but can be differentiated by hairs, glandular hairs, and pigment cells.View full abstractDownload PDF (301K) -
Components of the Leaves of Sophora angustifolia Sieb. et. Zucc., Vicia hirsuta Koch., and Linaria japonica MiqTashichiro Nakaoki, Naokata Morita, Hiroaki Mototsune, Akio Hiraki, Te ...1955 Volume 75 Issue 2 Pages 172-176
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe pale yellow needle crystals of m.p. 235-238°, obtained in 0.5% yield from the stem leaves of Sophora angustifolia Sieb. et Zucc., was found to be identical with luteolin 7-glucoside, while the two kinds of flavonoids, the pale yellow microneedles of m.p. 232-233° (yield, 2.5-3%) and the yellow leaflet crystals of m.p. 184-186° (yield, 0.005-0.01%), obtained from Vicia hirsuta Koch were found to be respectively identical with apiin and quercitrin. The pale yellow microneedles of m.p. 248-250°, obtained in 1-1.2% yield from Linaria japonica Miq., was found to be identical with pectolinarin isolated from Linaria vulgaris Mill., chemical composition being scutellarein-6, 3′-dimethyl ether-7-rhamnoglucoside.View full abstractDownload PDF (851K) -
Syntheses of 8- or 10-Alkylated DecahydroquinolinesNorio Sugimoto, Hiroshi Kugita, Tomoo Fujita1955 Volume 75 Issue 2 Pages 177-179
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBased on the fact that a part of the morphine skeleton contains a decahydroisoquinoline ring, some hydroisoquinolines of such series and related hydroquinoline derivatives were studied in connection with the analgesic action that might be shown by these compounds. As a preliminary, 10-phenyl- and 10-anisyldecahydroquinolines were prepared by the high pressure catalytic reduction of 2-substituted 2-(β-cyanoethyl)-cyclohexane and 8-cyclohexyldecahydroquinoline by the same procedure from 6-cyclohexylidene-2-(β-cyanoethyl)-cyclohexanone. The N-alkyl derivatives were totally devoid of or possessed only a weak analgesic action.View full abstractDownload PDF (521K) -
Synthesis of 2-Methyl-9-ethoxycarbonyldecahydroisoquinolineNorio Sugimoto, Susumu Oshiro, Seiichi Saito1955 Volume 75 Issue 2 Pages 180-183
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe preparation of 2-methyl-9-ethoxycarbonyldecahydroisoquinoline was carried out by the application of the Robinson cyclization. The condensation of 1-diethylamino-3-butanone methiodide with 1-methyl-3-ethoxycarbonyl-4-piperidone yielded 2-methyl-6-oxo-9-ethoxy carbonyl-Δ5, 10-octahydroisoquinoline (III, R=H). Hydrogenation of (III) in the presence of the Adams' platinum catalyst yielded 2-methyl-6-hydroxy-9-ethoxycarbonyldecahydroisoquinoline (IV), which, on selective oxidation with activated manganese dioxide, gave 2-methyl-6-oxo-9-ethoxycarbonyldecahydroisoquinoline (VI). Reaction of (VI) with ethylenethioglycol formed a thioketal with a characteristic odor. This thioketal was converted to 2-methyl-9-ethoxycarbonyldecahydroisoquinoline (VIII) by refluxing with Raney nickel in ethanol. 2-Methyldecahydroisoquinoline-9-carboxylic acid lactone-6 (V) was prepared by reacting 2-methyl-9-ethoxycarbonyl-6-hydroxydecahydroisoquinoline (IV) in benzene with hydrochloric acid gas. Pharmacological tests showed that (III, R=H) and (V) possessed activities 1/25 to 1/30 of that of morphine, while (VI) and (VIII) showed only a slight activity.View full abstractDownload PDF (787K) -
Synthesis of 1-Aza-3, 4:1′, 2′-(4′, 5′-dimethoxybenzo)-bicyclo [3:3:1] nonaneNorio Sugimoto, Hiroshi Kugita1955 Volume 75 Issue 2 Pages 183-187
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAs a preliminary to the synthesis of 9-azamorphinan, 1-azoniabicyclo [3:3:1] nonane chloride was prepared by the condensation of β-(3, 4-dimethoxyphenyl) piperidine with formaldehyde and hydrochloric acid. Attempt to obtain the same compound by the formylation of β-(3, 4-dimethoxyphenyl) piperidine followed by cyclization with phosphoryl chloride ended fruitless, the product being a resinous matter. In short, the Bischler-Napieralski reaction of the acyl compound of phenethylamine, in which the amine nitrogen and the carbon in β-position are bonded with several numbers of methylene groups, is extremely difficult and requires further study.View full abstractDownload PDF (777K) -
Mutual Solubilities of Triethylamine-H2O-NaOH and Triethylamine-H2O-KOH SystemsTakeo Ishiguro, Masao Ikushima, Naofumi Koga, Masami Yagyu1955 Volume 75 Issue 2 Pages 188-192
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe lower critical solution point of the triethylamine-water system was assumed to exist at 17.6° at the composition of 28-32% of triethylamine. Mutual solubility of the triethylamine-water-sodium hydroxide system at 0, 20, 40, 60, and 70°, and triethylamine-water-potassium hydroxide system at 0, 30, and 60°, were determined. It was thereby found that, in the amine-water-alkali hydroxide system, the mutual solubility decreases with the increase of temperature at the same composition, while the concentration of the amine in the upper layer increases with the increasing concentration of the alkali hydroxide in the lower layer, at a definite temperature. In other words, the concentration of the amine coexistent with alkali hydroxide solution increases with the increasingly high temperatures. Comparison of the dehydration effect of sodium and potassium hydroxides against the amine showed that sodium hydroxide possessed larger effect at a low temperatures while potassium hydroxide was better at higher temperatures. By the utilization of these properties, the best method for the dehydration of the amine or its isolation from an aqueous solution can easily be obtained.View full abstractDownload PDF (942K) -
Colorimetric Determination of DihydrostreptomycinKiichiro Kakemi, Takaichi Arita1955 Volume 75 Issue 2 Pages 192-194
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIt has been found that streptomycin and dihydrostreptomycin form sensitive orange red color with sodium pentacyanoamminferroate and potassium ferricyanide, on the addition of acetone, and that the relationship between the optical density of this coloration and the concentration of the streptomycin followed the Beer's law. This coloration was utilized in the colorimetric determination of dihydrostreptomycin. The determination was carried out with the ordinary dihydrostreptomycin sulfate as the standard. The potency obtained by this method and that from microbiological assay were found to agree. Potency determinations were carried out on the market products of dihydrostreptomycin.View full abstractDownload PDF (480K) -
Colorimetric Determination of OxytetracyclineKiichiro Kakemi, Toyozo Uno, Masayoshi Samejima1955 Volume 75 Issue 2 Pages 194-196
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDetermination of hydroxytetracyclin was found to be possible by the following method. A mixture of 1% ammonium molybdate solution and hydroxytetracyclin solution in an acetic acid buffer of pH 4 is heated at 60° for 15 minutes, shaken with an equal volume mixture of ethyl acetate and ether, and the aqueous layer is diluted to a definite volume. This aqueous solution is optically measured in a 2-cm. cell with S50 and S66 filters, and the value of ES50-ES66 is calculated.View full abstractDownload PDF (450K) -
Methylcellulose and Ethylhydroxyethylcellulose Dihydrogen DicarbonatesKiichiro Kakemi, Toyozo Uno, Fuyuki Kusuda, Tadao Ida1955 Volume 75 Issue 2 Pages 197-200
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAs the monoesters of dibasic acids of methylcellulose and ethylhydroxyethylcellulose, methylcellulose hydrogen phthalate (I) and hydrogen succinate (II), and ethylhydroxyethylcellulose hydrogen phthalate (III) and hydrogen succinate (IV) were prepared in order to examine their utility as an enteric coating agent. It was thereby found that (I) and (III) were extremely good enteric coating agents as evidenced by successful attainment of the objective by coating in the usual manner in a coating pan the ethylene dichloride and ethanolic or chloroform and ethanolic solution of (I) and (III), or acetone and ethanolic solution of (III). However, (II) and (IV) were found to be practically insoluble in organic solvents, that their coating was effected by preparing an aqueous solution of the methylcellulose and ethylhydroxyethylcellulose sodium succinate. (IV) was found to be possible in using as an enteric coating but (II) was found to swell by moisture and unsuitable as an enteric coating agent.View full abstractDownload PDF (724K) -
Condensation Product and Constitution of 2-Hydrazono-4-thiazolidone. (Suppl.)Hyozo Taniyama, Bompei Yasui1955 Volume 75 Issue 2 Pages 200-203
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOn heating, 2-hydrazono-4-thiazolidone (II) or its hydrochloride yielded colorless needle crystals of m.p. 325° (decomp.), which were assumed to be bis [4-oxothiazolidylidene-(2)]-hydrazine (III) because of the same melting point and similar properties as those of (III) obtained by Stephen and Wilson by the condensation of ethyl chloroacetate and hydrazodithiodicarbamide. In order to further confirm this structure, 1 mole of hydrazine was reacted with 2-thio-4-thiazolidone by which the substance of the same melting point as the foregoing two was obtained by the liberation of hydrogen sulfide. The alkylation of this product yielded 3-alkyl derivatives which were found by admixture to be identical with the 3-alkyl derivatives of (III) obtained by different routes of synthesis. The foregoing results have confirmed the correctness of the structure of (III). It was assumed from experimental results that the reaction mechanism whereby (III) is formed from (II) occurs first by the bimolecular condensation of (II) with subsequent liberation of hydrazineView full abstractDownload PDF (729K) -
Syntheses and Antibacterial Properties of Acylnaphthoquinones. (1)Jun-ichi Hase, Toshiko Nishimura1955 Volume 75 Issue 2 Pages 203-207
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to test their antibacterial properties, various kinds of 2-acyl-3-hydroxy-1, 4-naphthoquinones possessing a straight alkyl chain were prepared. The compounds obtained during the course of these synthetic procedures are also described.View full abstractDownload PDF (785K) -
Syntheses and Antibacterial Properties of Acylnaphthoquinones. (2)Jun-ichi Hase, Toshiko Nishimura1955 Volume 75 Issue 2 Pages 207-209
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSGrowth inhibitory action of acylnaphthoquinones and their allied compounds were examined against bacteria. Of these compounds tested, 2-dodecanoyl-3-hydroxy-1, 4-naphthoquinone successfully inhibited the growth of Staphylococcus aureus in 1:25, 600, 000 dilution in the Knight synthetic medium.View full abstractDownload PDF (329K) -
Ken'ichi Takeda, Hiroshi Osaka1955 Volume 75 Issue 2 Pages 210-212
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) Application of metallic sodium to 1-methylnaphtho [2, 1-b] furan in liquid ammonia, with ether as a solvent, at -40° to -60°, results in the formation of 1-isopropyl-2-naphthol, which was identified with the product synthesized from 1-aceto-2-naphthol.
2) The same treatment of 2-methylnaphtho [2, 1-b] furan does not result in the consumption of sodium. Its reduction with sodium and ammonium chloride in liquid ammonia yielded 1-propyl-2-naphthol, 5, 8-dihydro-1-propyl-2-naphthol, and 5, 6, 7, 8-tetrahydro-1-propyl-2-naphthol. The first and last compounds were confirmed with synthetic specimens, and the structure of the other compound was assumed from its ultraviolet and infrared absorption spectra.View full abstractDownload PDF (617K) -
Iodination of CarbostyrilEiji Ochiai, Tetsuo Yokokawa1955 Volume 75 Issue 2 Pages 213-214
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSTreatment of the adduct of quinoline 1-oxide and tosyl chloride with 10% sodium carbonate results in the formation of carbostyril in about 83% yield. Iodination of the carbostyril with iodine chloride in glacial acetic acid yields a monoiodine substituent of m.p. 250° which was determined as 3-iodocarbostyril by deriving it to 3-aminoquinolin. The yield of the iodine derivative was 80-90%. Nitration of 3-iodocarbostyril yielded a mononitro compound of m.p. 328° (decomp.), which was assumed to be a 6-nitro compound.View full abstractDownload PDF (266K) -
On the Therapeutic Effect of Monosubstituted ProcainesTozaburo Kurihara, Hiroshi Niwa, Takashi Toda1955 Volume 75 Issue 2 Pages 215-218
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to make systematic observations on the capacity of the auxiliary atomic groups with local anesthetic properties, 22 kinds of ortho- or meta-substituted derivatives of procaine were prepared, 11 of which being new compounds. Tests of surface filtrating anesthetic action and toxicity revealed that the substituents in general increased the effect of procaine without giving a large effect on the toxicity. Electron-donating radicals were more effective in the ortho-position than in the meta, while electron-attracting groups seemed to be more effective in the meta-position. Of the compounds prepared, those introduced with thiomethyl or thioethyl groups were the most effective, showing 1.5 times the surface anesthetic action than cocaine. Alkoxyl and halogen substituents followed the above in efficacy.View full abstractDownload PDF (590K) -
The Anthraquinone Coloring Matter from Damnacanthus major, D. major var. parvifolius, and D. indicus var. microphyllus. (1)Susumu Nonomura1955 Volume 75 Issue 2 Pages 219-221
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAnthraquinone pigments were isolated from Damnacanthus major Sieb. et Zucc., D. major Sieb. et Zucc. var. parvifolius Koidz., and D. indicus Gaertner fil. var. microphyllus Makino (Rubiacea family), and were designated as follows: Damnacanthal (m.p. 208°), juzunal (m.p. 248°), damnacanthol (m.p. 288°), damnidin (m.p. 180°), and a neutral substance (m.p. 160°). Of these, damnacanthal is identical with the substance, C16H10O5 (B), isolated by Perkin from Morinda umbellata L. It is an anthraquinone containing α-methoxyl and is saponified by sulfuric acid or alkali to form nordamnacanthal, m.p. 218°, which is the decarboxylation product of m.p. 218° obtained by Perkin. Heating of damnacanthal with alkali yielded purpuroxanthin.View full abstractDownload PDF (509K) -
The Anthraquinone Coloring Matter from Damnacanthus major, D. major var. parvifolius, and D. indicus var. microphyllus. (2)Susumu Nonomura1955 Volume 75 Issue 2 Pages 222-224
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDamnacanthal (I), an anthraquinone isolated from a plant of Damnacanthus genus, possesses a free hydroxyl in β-position because it is acetylated and is methylated by diazomethane. Its aldehyde group is present in the ortho-position to the hydroxyl since the Perkin reaction of (I) gives a coumarin derivative and forms a triacetate by acetallike acetylation. Juzunal, another anthraquinone isolated from the same genus, is assumed to be hydroxydamnacanthal. Demnacanthol is assumed to be lucidin α-methyl ether.
Damnidin, another of the anthraquinones isolated, corresponds to C17H16O5, and forms a triacetate. The neutral substance also obtained in the course of the isolation corresponds to C30H52O and forms an acetate.View full abstractDownload PDF (461K) -
The Constitution of DamnacanthalSusumu Nonomura1955 Volume 75 Issue 2 Pages 225-227
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOxime, hydrazone, and anil of damnacanthal (I) were prepared in order to confirm the presence of an aldehyde group in (I). Schmidt reaction of (I) gives damnacanthic nitrile (II) and oxidation of (I) with alkaline H2O2 yields damnacanthic acid, which was derived to purpuroxanthin dibromide through munjistin. Saponification of (II) was difficult due to steric hindrance but it was converted to purpuroxanthin and confirmed by paper chromatography. Conversion of nordamnacanthal oxime to the nitrile and its saponification was difficult but it was also converted to purpuroxanthin and confirmed by paper chromatography. It was concluded from the measurement of ultraviolet absorption specrum of (I) that it is 1-methoxy-2-formyl-3-hydroxyanthraquinone.View full abstractDownload PDF (487K) -
Syun Iseda, Kazuyoshi Yagishita1955 Volume 75 Issue 2 Pages 230-231
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSEthanolic extract of the calyx of dried Kaki (fruit of Diospyros Kaki L. fil.) was prepared, the portion insoluble in water and dilute alkali (1.2%) was collected, and ether-insoluble portion (0.35%) was removed. Ether-soluble portion yielded hydroxytriterpenic acid (0.37%) as its potassium salt. The neutral substance soluble in ether, 0.375%. The triterpenic acid was repeatedly purified as the potassium salt and acetylated. The fractional crystallization of the product from methanol yielded acetyloleanolic acid as the most sparingly soluble component, followed by acetylbetulinic acid. Hydrolysis of the remainder and recrystallization of the product from methanol yielded ursolic acid. Recrystallization of the mixture of the methyl ester of the acetylated product easily gave the pure product of methyl acetyloleanolate. The portion of the ethanolic extract soluble in water was treated with lead acetate to remove portion precipitating with it and submitted to paper chromatography from which glucose and fructose were identified. Alkalisoluble portion yielded acidic substances extracted by NaHCO3 (0.255%), Na2CO3 (0.13%), and NaOH (0.15%), 1.4% of phlobaphene (?), and 0.105% of a neutral fatty oil. The first two of the acidic substances gave yellowish green coloration with ferric chloride.View full abstractDownload PDF (457K) -
Seiichi Ohkuma1955 Volume 75 Issue 2 Pages 232-233
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSpecific color reaction for diethylamine (I) is to mix 1 drop of (I) or its hydrochloride solution with 1 drop of 5% sodium nitroprusside (II) solution, 1 drop of 5% potassium ferricyanide (III) solution, and 1 drop of 2N Na2CO3 solution, and warming the mixture in a water bath (90°) for about 15 seconds by which the reaction mixture acquires a pale brownish yellow color which turns from indigo blue, through purple, to purplish red on cooling in air or water. The mechanism of this coloration may be assumed as the oxidation of (I) by (II) and (III) to form acetaldehyde which reacts with (I) and (II) to give the color reaction peculiar to aliphatic secondary amines.View full abstractDownload PDF (331K) -
Synthesis of Monoalkylsuccinic Acid DihydrazidesYoshiyuki Takata, Ken-ichi Yamamoto, Yoshihiro Takata1955 Volume 75 Issue 2 Pages 233-234
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAlkylsuccinic acid dihydrazides, where the alkyl group was ethyl, propyl, butyl, isoamyl, hexyl, heptyl, or octyl, were prepared and their antibacterial action against Human type tubercle bacilli, H37 Rv, was tested. All the compounds were able to inhibit the growth in 200γ/cc. concentration and no difference in action due to alkyl chain was observed.View full abstractDownload PDF (272K) -
Comparison with TetrodotoxinAkira Yokoo, Shiro Morosawa1955 Volume 75 Issue 2 Pages 235-236
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSResults of paper chromatography and comparison of infrared absorption curves suggest that spheroidine, a crystalline poison of the globefish ovaries obtained by the writers, and tetrodotoxin obtained by Kawamura and Tsuda, are identical substances.View full abstractDownload PDF (320K) -
Infrared Spectra of Sugars and GlucosidesMitsuo Takahashi1955 Volume 75 Issue 2 Pages 237-238
Published: February 25, 1955
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn connection with the study of sugars and glycosides by infrared absorption spectra, the present studies and those reported by Whistler and House and by Barker, et al. were compared. It was thereby found that the results of Barker and of the writer agree well but not that of Whistler and the writer. Barker and others concluded that the infrared spectra of the α, β-series of the reducing sugars and methyl-glucosides or polysaccharides made it possible to discriminate between α and β. The present writer made further clarification of this theory and assumed that it might be possible to discriminate the structural difference of cis and trans of the asymmetric C1 and C2 carbons in sugars and glucosides.View full abstractDownload PDF (396K)
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