Chemical and Pharmaceutical Bulletin

4, 5-Substituted Pyridazines. V. Acylation of 4-Amino-3, 6-dichloropyridazine.

Tsukasa Kuraishi

1958 Volume 6 Issue 4 Pages 331-333
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.331

JOURNAL FREE ACCESS

Show abstractHide abstract

2-Phenyl-6-chloro-oxazolo [5, 4-c] pyridazine (IV) was prepared by heating 4-amino-3, 6-dichloropyridazine (I) or 4-amino-6-chloro-3-pyridazinol (V) with excess of benzoyl chloride. The synthesis of 4-amino-3-pyridazinol (VI), 5-amino-4-chloro-3-pyridazinol (X), 5-acylamido-4-chloro-3-pyridazinol (XI and XII), and 5-amino-3-pyridazinol (XIII) was also described.

View full abstract

Download PDF (422K)
Studies on Pyrimidine Derivatives. I. Synthesis of Thiazolo [5, 4-d]-pyrimidines and Related Compounds. (1).

Torizo Takahashi, Takio Naito, Shoji Inoue

1958 Volume 6 Issue 4 Pages 334-338
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.334

JOURNAL FREE ACCESS

Show abstractHide abstract

The reaction of 2-chloro-4-thiocyano-5-nitropyrimidine with alcohol, sodium alkoxide, or sodium ethanethioxide was studied, and 5-nitrouracil, 2-ethoxy-4-mercapto-5-nitro-pyrimidine (IV), and 2-ethylthio-4-thiocyano-5-nitropyrimidine (VII) were obtained from the above reagents, while (IV) was reduced to the corresponding amino derivative (VIII). 2-Amino-5-ethylthio-thiazolo [5, 4-d] pyrimidine was synthesized by the reduction of (VII). Treatment of (VIII) with formic acid, acetic anhydride, or potassium methylxanthate, gave 5-ethoxy-, 2-methyl-5-ethoxy-, and 2-mercapto-5-ethoxythiazolo [5, 4-d] pyrimidine, respectively.

View full abstract

Download PDF (616K)
Studies on Pyrimidine Derivatives. II. Synthesis of Thiazolo [5, 4-d] pyrimidines and Related Compounds. (2).

Takio Naito, Shoji Inoue

1958 Volume 6 Issue 4 Pages 338-343
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.338

JOURNAL FREE ACCESS

Show abstractHide abstract

1) The reaction of 2-chloro-4-thiocyano-5-nitropyrimidine (I) with aq. NH₄OH, EtNH₂, thiourea, or sodium phenoxide gave 2, 4-disubstituted derivatives. The reaction of (I) with ethanolic NH₄OH and aniline respectively gave 2-amino-4-thiocyano-5-nitropyrimidine (V) and 2-anilino-4-thiocyano-5-nitropyrimidine (IX), and the reaction of (V) or (IX) with sodium alkoxide gave 2-amino-4-mercapto-(XIV) and 2-anilino-4-mercapto-5-nitropyrimidine (XV). 2) The reduction of (V) and (IX) afforded the corresponding 2-aminothiazolo [5, 4-d]-pyrimidines, and the reduction of (XIV) and (XV) gave 2, 5-diamino-4-mercapto-(XVII) and 2-anilino-4-mercapto-5-aminopyrimidine (XVIII), respectively. The cyclization of (XVII) and (XVIII) with formic acid, acetic anhydride, benzoyl chloride, or potassium methylxanthate, gave the corresponding 2-substituted (H, CH₃, C₆H₅, SH) thiazolo [5, 4-d]-pyrimidines. 3) In the presence of alkali, 2-aminothiazolo [5, 4-d] pyrimidines were hydrolysed to the 4-mercapto-5-aminopyrimidine derivatives via the (4-mercapto-5-pyrimidyl) ureas.

View full abstract

Download PDF (721K)
Studies on Pyrimidine Derivatives. III. Synthesis of Thiazolo [5, 4-d] pyrimidines and Related Compounds. (3).

Shoji Inoue

1958 Volume 6 Issue 4 Pages 343-346
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.343

JOURNAL FREE ACCESS

Show abstractHide abstract

The reduction product of 2-chloro-4-thiocyano-5-nitropyrimidine (I) was found to be 2-chloro-4-thiocyano-5-aminopyrimidine (II). Reaction of (II) with sodium ethoxide or ethanethioxide gave 2, 4-diethoxy-5-aminopyrimidine and 2-ethylthio-4-thiocyano-5-amino-pyrimidine. 2-Chloro-4-mercapto-5-aminopyrimidine reacted with acetic anhydride and the resulting product was 2-methyl-5-chlorothiazolo [5, 4-d] pyrimidine, the chlorine of which is reactive.

View full abstract

Download PDF (561K)
Studies on Pyrimidine Derivatives. IV. Synthesis of Thiazolo [5, 4-d] pyrimidines and Related Compounds. (4).

Shoji Inoue

1958 Volume 6 Issue 4 Pages 346-349
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.346

JOURNAL FREE ACCESS

Show abstractHide abstract

The reaction of 2, 4-dimercapto-5-aminopyrimidine with acetic anhydride and benzoyl chloride gave 2-methyl-5-mercapto-(VII) and 2-phenyl-5-mercaptothiazolo [5, 4-d] pyrimidine, respectively. By desulfurization of (VII) with Raney nickel, 2-methylthiazolo [5, 4-d] pyrimidine was obtained. The corresponding thiazolo [5, 4-d] pyrimidines were prepared from 2-ethylthio-4-hydroxy-5-acylamidopyrimidine in the presence of phosphorus pentasulfide.

View full abstract

Download PDF (548K)
Studies on Pyrimidine Derivatives. V. Synthesis of Thiazolo [5, 4-d] pyrimidines and Related Compounds. (5).

Shoji Inoue

1958 Volume 6 Issue 4 Pages 349-352
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.349

JOURNAL FREE ACCESS

Show abstractHide abstract

4-Mercapto-5-aminopyrimidine (III) was prepared by the following two reactions. 1) The reaction of phosphorus pentasulfide on 4-hydroxy-5-aminopyrimidine. 2) The dehalogenation of 4-mercapto-5-amino-6-chloropyrimidine. Thiazolo [5, 4-d] pyrimidine and 2-methyl-, 2-phenyl-. and 2-mercaptothiazolo [5, 4-d]-pyrimidines were prepared from (III).

View full abstract

Download PDF (557K)
Studies on Pyrimidine Derivatives. VI. Synthesis of Thiazolo [5, 4-d] pyrimidines and Related Compounds. (6).

Shoji Inoue

1958 Volume 6 Issue 4 Pages 352-355
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.352

JOURNAL FREE ACCESS

Show abstractHide abstract

By treatment with hydrogen peroxide 2-methyl-7-mercaptothiazolo [5, 4-d] pyrimidine was easily oxidized to the 7-hydroxy compound, and it was converted into the 7-chloro derivative. 7-Substituted (-OC₂H₅, -OC₆H₅, -NHC₂H₅ and -NHC₆H₅) 2-methylthiazolo-[5, 4-d] pyrimidines were synthesized from 7-chloro-2-methylthiazolo [5, 4-d] pyrimidine. 2, 7-Dimercaptothiazolo [5, 4-d] pyrimidine was prepared from 4, 6-dimercapto-5-amino-pyrimidine and potassium methylxanthate. The heating of 4-mercapto-5-amino-6-benzylthio-pyrimidine (XII) with formic acid or phosgene also resulted in ring closure to afford 7-benzylthio-thiazolo [5, 4-d] pyrimidine or 2-hydroxy-7-benzylthio-thiazolo [5, 4-d]-pyrimidine (XIV). Cleavage of (XIV) with sodium hydroxide solution was examined and (XII), the starting material, was recovered by the liberation of CO₂.

View full abstract

Download PDF (547K)
Structure of Longifolene.

Isao Ogura

1958 Volume 6 Issue 4 Pages 356-358
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.356

JOURNAL FREE ACCESS

Show abstractHide abstract

Naffa and Ourisson proposed a structure of longifolene from the investigation of its X-ray, infrared, and Raman spectra, and from chemical reactions of five-membered ring having a double bond. For the purpose of chemical certification of five- and seven-membered rings in the molecule, other than those verified by Naffa and others, examination was made on dehydrogenation of α-longifolic acid and a monobasic acid which was obtained from longicamphenylone by decomposition. 4, 8-Dimethylazulene was obtained from α-longifolic acid in this experiment confirming the structural formula suggested by Naffa and Ourisson.

View full abstract

Download PDF (410K)
Synthesis of rac-Dihydrorotundine.

Shigehiko Sugasawa, Kitaro Mizukami

1958 Volume 6 Issue 4 Pages 359-365
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.359

JOURNAL FREE ACCESS

Show abstractHide abstract

A synthesis of rac-dihydrorotundine (I) was described. Methylsuccinic anhydride was condensed with ethyl 3, 4-dimethoxyphenethylaminoacetate to yield a single methyl-succinamic acid (XI), having the methyl substituent β to the amido group. This was esterified, cyclized, and reduced, and thus the tetrahydroisoquinoline base (XIII) was obtained. Dieckmann cyclization of the latter by means of sodium hydride in boiling toluene gave a fair yield of the keto-ester (XV), but its ketonic fission proceeded with difficulty and thus the ketone (XVI) was produced only in a low yield. When dimethyl ketal (XVII) of (XVI) was submitted to distillation in vacuo a loss of one molecule of methanol took place and rac-dihydrorotundine (I) was collected as a viscous distillate, which was characterized as its crystalline methiodide. rac-Dihydro-norrotundine (X) was also prepared as a model substance and its behavior towards catalytic hydrogenation was studied.

View full abstract

Download PDF (892K)
Uber die Synthese der heterozyklischen Verbindungen mit Stickstoff. CXII. Synthese der Derivate des Oxypyridins.

Torizo Takahashi, Fumio Yoneda

1958 Volume 6 Issue 4 Pages 365-369
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.365

JOURNAL FREE ACCESS

Show abstractHide abstract

Durch Einwirkung von Phenacylbromid auf 2-Pyridon-silbersalz in Athanol wurde 2-Phenacyloxy-pyridin erhalten. 2-Pyridon-natriumsalz lieferte aber durch Einwirkung von Phenacylbromid in Athanol N-Phenacyl-2-pyridon. 2-Pyridon-silbersalz reagierte mit 1-Chlor-4-nitrobenzol, 1-Chlor-2-nitrobenzol bzw. 1-Chlor-2, 4-dinitrobenzol nur in Gegenwart von Kupferpulver, wobei die N-substituierten Pyridone erhalten wurden. Die so erhaltenen Substanzen wurden miteinander in ihren UV-Spektren vergleichsweise untersucht. Auch 4-Pyridon-silbersalz lieferte durch Einwirkung von Phenacylbromid in Athanol N-Phenacyl-4-pyridon.

View full abstract

Download PDF (564K)
Sulfur-containing Pyridine Derivatives. LVI. Smiles Rearrangement of Pyridine Derivatives and Synthesis of Benzopyrido-and Dipyrido-1, 4-thiazine Derivatives. (4).

Torizo Takahashi, Yoshifumi Maki

1958 Volume 6 Issue 4 Pages 369-373
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.369

JOURNAL FREE ACCESS

Show abstractHide abstract

1) General considerations were made concerning the mechanism of Smiles rearrangement of pyridine derivatives as a result of further investigation of reaction conditions employed. 2) A 10-substituted dipyrido-1, 4-thiazine derivatives were synthesized with a view to investigating pharmacological action analogous to chlorpromazine.

View full abstract

Download PDF (637K)
Synthesis of Analgesics. XIX. Antipyrine Derivatives. (6).

Torizo Takahashi, Ken Kanematsu

1958 Volume 6 Issue 4 Pages 374-378
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.374

JOURNAL FREE ACCESS

Show abstractHide abstract

1) 4-Formylantipyrine (III), 4-acetylantipyrine (XVIII), and 1, 2-diphenyl-3-methyl-4-formyl-(IV) and 1, 2-diphenyl-3-methyl-4-acetyl-5-pyrazolone (XIX), when heated with sulfur in morpholine, yielded the corresponding compounds of morpholides (V, XX, VI, and XXI). These morpholides were submitted to hydrolysis with aqueous or alcoholic alkali and respectively gave 4-antipyrinecarboxlic acid (VII), 4-antipyrineacetic acid (XXII), 1, 2-diphenyl-3-methyl-5-pyrazolone-4-carboxlic acid (VIII), and 1, 2-diphenyl-3-methyl-5-pyrazolone-4-acetic acid (XXIII), each in a good yield. 2) 4-Antipyrinecarboxamide (XIII) was converted to 4-aminomethylantipyrine (XXIV) by lithium aluminum hydride. However, hydrogenation of N, N-dialkyl-4-antipyrine-carboxamides (XIV) and (XV) under similar conditions gave 4-formylantipyrine (III).

View full abstract

Download PDF (643K)
Uber die Synthese der heterozyklischen Verbindungen mit Stickstoff. CXIII. Synthese der Azaphenoxazinderivate. (2).

Torizo Takahashi, Fumiro Yoneda

1958 Volume 6 Issue 4 Pages 378-381
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.378

JOURNAL FREE ACCESS

Show abstractHide abstract

Durch die Kondensation von Harnstoff mit o-Aminophenol wurde Benzoxazol-2 (3H)-on in 88∼90-proz. Ausbeute dargestellt. Das letztere lieferte durch Einwirkung von Benzylchlorid, 2-Diathylaminoathylchlorid bzw. 3-Dimethylaminopropylchlorid in Gegenwart von Alkali 3-Benzyl-, 3-(2-Diathylaminoathyl)-bzw. 3-(3-Dimethylaminopropyl)-benzoxazol-2 (3H)-on, ferner trat beim Erhitzen von diesen Substanzen in alkoholischer Kalilosung die o-Benzyl-, o-(2-Diathylaminoathylamino)-bzw. o-(3-Dimethylaminopropyl-amino) phenol ergebende Ringoffnung ein. Bei der Einwirkung von 2-Chlor-3, 5-dinitropyridin bzw. 2-Brom-3-nitro-5-chlorpyridin auf den oben beschriebenen N-substituierten o-Aminophenolen wurden die entsprechenden N-substituierten Azaphenoxazine dargestellt.

View full abstract

Download PDF (596K)
Synthesis of Related Compounds of Thiosemi-carbazide. IV. 1-(1, 3, 4-Thiadiazol-2-yl)-2-pyrazolin-5-one and Tetrazolo [4, 5-a]-1, 3, 4-thiadiazole Derivatives.

Matao Kanaoka

1958 Volume 6 Issue 4 Pages 382-386
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.382

JOURNAL FREE ACCESS

Show abstractHide abstract

1) 1-(5-R-1, 3, 4-Thiadiazol-2-yl)-3-methyl-4-R'-2-pyrazolin-5-one (R'=H, iso-C₃H₇) (III) were synthesized starting with 2-hydrazino-5-R-1, 3, 4-thiadiazole (I : R=CH₃, C₂H₅, n-C₃H₇, iso-C₄H₉, C₆H₅), and reacting them with ethyl acetoacetate or ethyl 3-acetyliso-valerate to form 5-R-1, 3, 4-thiadiazolylhydrazone (II). 2) 2-R-Tetrazolo [4, 5-a]-1, 3, 4-thiadiazole, compound analogous to 8-azaguanine, were synthesized by the reaction of 2-hydrazino-5-R-1, 3, 4-thiadiazole (I) with sodium nitrite in diluted acetic acid.

View full abstract

Download PDF (534K)
Microbiological Hydroxylation of Steroids. IV. 7α, 15β-Dihydroxylation of Progesterone by Syncephalastrum sp. (2).

Kyosuke Tsuda, Toshinobu Asai, Eiji Ohki, Atsuji Tanaka, Masako Hattor ...

1958 Volume 6 Issue 4 Pages 387-391
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.387

JOURNAL FREE ACCESS

Show abstractHide abstract

The microbiological transformation of progesterone with Syncephalastrum sp. was carried out and the dihydroxyprogesterone so obtained was found to have the hydroxyl groups in the 7α-and 15β-positions.

View full abstract

Download PDF (678K)
Die Quaternisierungsreaktion am Ringstickstoff von stereoisomeren Hexahydrojulolidine.

Kyosuke Tsuda, Seitaro Saeki

1958 Volume 6 Issue 4 Pages 391-393
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.391

JOURNAL FREE ACCESS

Download PDF (451K)
Studies on Acylase Activity and Microorganisms. VIII. Enzymatic Hydrolysis of 6-N-Benzoyl-L-lysine.

Yukio Kameda, Etsuko Toyoura, Yukio Kimura, Katsuhiko Matsui

1958 Volume 6 Issue 4 Pages 394-395
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.394

JOURNAL FREE ACCESS

Show abstractHide abstract

It was found that a strain of Pseudomonas sp., KT 83, contains an enzyme which hydrolyzes 6-N-benzoyl-L-lysine. By incubating 6-N-benzoyl-DL-lysine with bacterial mass, acetone-dried powder, cell-free extract, or cell-free acetone powder of KT 83, L-lysine, 6-N-benzoyl-D-lysine, and benzoic acid were obtained in a good yield.

View full abstract

Download PDF (393K)
Studies on Acylase Activity and Microorganisms. IX. Enzymatic Resolution of Tryptophan by a Strain of Soil Bacteria.

Yukio Kameda, Etsuko Toyoura, Yukio Kimura, Buhei Okino

1958 Volume 6 Issue 4 Pages 395-397
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.395

JOURNAL FREE ACCESS

Show abstractHide abstract

It was found that a strain of Pseudomonas sp., KT 104, isolated from the soil of a bamboo thicket in Kanazawa, has the ability to hydrolyze asymmetrically 1-N-acetyl-DL-tryptophan to give L-tryptophan and 1-N-acetyl-D-tryptophan. The strain may be used in the form of bacterial mass, acetone-dried powder, or cell-free extract. KT 104 can be cultivated in a synthetic medium containing N-benzoylanthranilic, benzoic, p-hydroxybenzoic, salicylic, anisic, or phenylacetic acid as the sole source of carbon, and ammonia as the sole source of nitrogen, at 25°, for at least 3 generations.

View full abstract

Download PDF (502K)
Studies on the Constituents of the Seeds of Cassia obtusifolia L.I. The Structure of Obtusifolin.

Michio Takido

1958 Volume 6 Issue 4 Pages 397-400
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.397

JOURNAL FREE ACCESS

Show abstractHide abstract

From the seeds of Cassia obtusifolia L. (Leguminosae), a new anthraquinone pigment, obtusifolin, m.p. 237∼238°, was isolated along with chrysophanol and physcion. The structure of obtusifolin was established as 1-methoxy-2, 8-dihydroxy-3-methylanthraquinone.

View full abstract

Download PDF (580K)
Studies on Naphthyridines. III. Syntheses of 2, 10-Diazaanthracene and 1, 7-Naphthyridine.

Nobuo Ikekawa

1958 Volume 6 Issue 4 Pages 401-404
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.401

JOURNAL FREE ACCESS

Show abstractHide abstract

The reaction of sodium salt of 3-carboxyquinaldine and formaldehyde gave 2-hydroxyethyl-3-quinolinecarboxylic, acid lactone, which was led to the amide, and its oxidation gave 1-hydroxy-2, 10-diazaanthracene. 2, 10-Diazaanthracene was obtained from this 1-hydroxy compound. 1, 7-Naphthyridine was synthesized from 4-chloro-1, 7-naphthyridine via 4-hydrazino compound.

View full abstract

Download PDF (522K)
Studies on Naphthyridines. IV. Infrared Spectra of Naphthyridines.

Nobuo Ikekawa

1958 Volume 6 Issue 4 Pages 404-407
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.404

JOURNAL FREE ACCESS

Show abstractHide abstract

Infrared spectra of twelve kinds of naphthyridines were determined and compared with those of naphthalenes. It was found that in some kinds of compound, out-of-plane deformation vibrations of hydrogen atoms on the ring showed abnormal absorption.

View full abstract

Download PDF (436K)
Studies on Naphthyridines. V. Catalytic Reduction of Naphthyridines.

Nobuo Ikekawa

1958 Volume 6 Issue 4 Pages 408-411
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.408

JOURNAL FREE ACCESS

Show abstractHide abstract

Catalytic hydrogenation over palladium of 3-methyl-2, 7-naphthyridine gave 88% of 5, 6, 7, 8-tetrahydro compound and 12% of 1, 2, 3, 4-tetrahydro compound, that of 1, 6-naphthyridine and 7-methyl-1, 6-naphthyridine gave 1, 2, 3, 4-tetrahydro compounds, and that of 1, 7-naphthyridine gave 98% of 1, 2, 3, 4-tetrahydro compound and 2% of 5, 6, 7, 8-tetrahydro compound. The reaction mechanism of catalytic hydrogenation of naphthyridines was discussed.

View full abstract

Download PDF (539K)
Organic Analysis. X. Reaction Mechanism of 5-Hydroxytetralone with Glucose.

Tsutomu Momose, Yosuke Ohkura

1958 Volume 6 Issue 4 Pages 412-415
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.412

JOURNAL FREE ACCESS

Show abstractHide abstract

A fluorescent compound produced in the reaction of 5-hydroxy-1-tetralone with glucose in sulfuric acid was separated in crystalline form and its probable structure was forwarded as benzonaphthenedione. The same compound was also isolated from the reaction mixture of glyceraldehyde with the same reagent. The mechanism of these reactions was discussed.

View full abstract

Download PDF (501K)
Organic Analysis. XI. Infrared Spectra of Phenylsulfonyl Derivatives. (1). The SO₂ Stretching Frequencies.

Tsutomu Momose, Yo Ueda, Tatsuo Shoji

1958 Volume 6 Issue 4 Pages 415-421
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.415

JOURNAL FREE ACCESS

Show abstractHide abstract

Infrared spectra of 50 phenylsulfonyl derivatives were measured and substituent effect on the sulfonyl group was discussed. Inductive and mesomeric effects of substituents attached to the phenyl ring or directly to the sulfonyl group somewhat affected the frequencies of asymmetric and symmetric stretching vibrations of SO₂. The frequency shifts had some correlations with Hammett's σ-value of the chemical shifts of benzene derivatives. Synthesis of some phenylsulfonyl derivatives is also described.

View full abstract

Download PDF (753K)
Studies on Determination of Sapogenins in Plants belonging to Dioscorea growing in Japan. II. Determination of Diosgenin, Tokorogenin, and a New Genin contained in the Roots.

Masaharu Yamagishi, Isao Nakamura

1958 Volume 6 Issue 4 Pages 421-425
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.421

JOURNAL FREE ACCESS

Show abstractHide abstract

The alcoholic extract of roots of Dioscorea growing in Japan was hydrolyzed with hydrochloric acid and the resulting mixture of sapogenins was separated into pure diosgenin, tokorogenin, and yonogenin by adsorption chromatography on Florisil. Each of the products was determined colorimetrically with reagents containing antimony trichloride as the chief component.

View full abstract

Download PDF (543K)
Nonaqueous Polarography of Quinones. V. Half-wave Potentials of o-Quinones in Relation to Carcinogenesis of Polyaromatic Hydrocarbons.

Morizo Ishidate, Takashi (the Late)Isshiki, Keizo Tada

1958 Volume 6 Issue 4 Pages 425-429
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.425

JOURNAL FREE ACCESS

Show abstractHide abstract

The half-wave potentials of five homologous o-quinones shown below were measured under identical conditions by the nonaqueous polarography in glacial acetic acid containing 0.25N ammonium acetate : 1, 2-Naphthoquinone (o-NQ), 1, 2-anthraquinone (o-AQ), 9, 10-phenanthrenequinone (Ph. Q), benz [a] anthra-5, 6-quinone (o-BAQ), dibenz-[a, h] anthra-5, 6-quinone (o-DBAQ). The order of the ease with which they are reduced at the dropping mercury electrode are given by the following sequence : o-NQ > o-AQ > Ph.Q > o-DBAQ > o-BAQ This order agreed with the resonance theory as in the case of p-quinones described in a previous paper. From the standpoint of the order of E_1/2's of the above-mentioned o-quinones, it was found that they might play some important roles in the carcinogenesis of their parent hydrocarbons.

View full abstract

Download PDF (597K)
Studies on the Syntheses of Hydrogenated Quinolines and Isoquinolines as Analgesics. XV. Synthesis of 3-Hydroxy-N-methyl-7-aza-des-N-morphinan (9-Hydroxy-3-methyl-5, 10b-trimethylene-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrobenzo [f] isoquinoline).

Norio Sugimoto, Hiroshi Kugita

1958 Volume 6 Issue 4 Pages 429-433
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.429

JOURNAL FREE ACCESS

Show abstractHide abstract

3-Hydroxy-N-methyl-7-aza-des-N-morphinan was synthesized. Analgesic action of this compound, contrary to expectations, was not strong.

View full abstract

Download PDF (611K)
Structure of the Condensation product of Isonicotinylhydrazine and Sodium Glucuronate.

Morizo Ishidate, Terumi Nakajima

1958 Volume 6 Issue 4 Pages 433-437
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.433

JOURNAL FREE ACCESS

Show abstractHide abstract

1) The reaction of isonicotinylhydrazine with glucuronic acid or its sodium salt gave isonicotinylhydrazino-N-glucuronide and not isonicotinylhydrazone derivative. 2) The evidence that the N-glucuronide is in β-N-(glucopyranosid) uronic acid form was established by preparation of the pentaacetyl derivative of the glucuronide and its identification with the compound synthesized from isonicotinylhydrazine and methyl 2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate as well as by comparison of their infrared spectra with that of the related compounds.

View full abstract

Download PDF (602K)
Bile Acids and Steroids. X. On β-Spinasterol.

Kenichi Takeda, Tokuo Kubota, Yoshiki Matsui

1958 Volume 6 Issue 4 Pages 437-440
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.437

JOURNAL FREE ACCESS

Show abstractHide abstract

From the root of Bupleurum falcatum L., a fraction corresponding to β-spinasterol was obtained by fractional crystallization of the dinitrobenzoates. Further investigation on this sterol showed that this so-called β-spinasterol is impure, and is &lrtri;⁷-stigmastenol contaminated with a small amount of α-spinasterol.

View full abstract

Download PDF (518K)
Studies on Acylase Activity and Microorganisms. X. Enzymatic Resolution of Alloisoleucine by Soil Bacteria, KT 85 (Pseudomonas sp.).

Yukio Kameda, Etsuko Toyoura, Katsuhiko Matsui

1958 Volume 6 Issue 4 Pages 441-442
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.441

JOURNAL FREE ACCESS

Show abstractHide abstract

A strain of soil bacteria, KT 85 (Pseudomonas sp.), asymmetrically hydrolyzed N-acetyl-DL-alloisoleucine to give L-alloisoleucine and N-acetyl-D-alloisoleucine in a good yield.

View full abstract

Download PDF (384K)
Uber das 3, 5-Dinitro-2-pyridon.

Torizo Takahashi, Fumiro Yoneda

1958 Volume 6 Issue 4 Pages 442-443
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.442

JOURNAL FREE ACCESS

Download PDF (376K)
Die Synthese der Imidazopyridinderivate.

Torizo Takahashi, Fumiro Yoneda, Sofu Yoshimura

1958 Volume 6 Issue 4 Pages 443-444
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.443

JOURNAL FREE ACCESS

Download PDF (332K)
Several 2, 3-Cyclic Phosphates of D-Ribofuranoside and their Properties as Substrate of Ribonuclease

Tyunosin Ukita, Masachika Irie

1958 Volume 6 Issue 4 Pages 445-447
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.445

JOURNAL FREE ACCESS

Download PDF (457K)
On the Nomenclature of the Fluorescent Substances produced in the Culture of Eremothecium ashbyii

Satoru Kuwada, Toru Masuda, Toyokazu Kishi, Mitsuko Asai

1958 Volume 6 Issue 4 Pages 447
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.447

JOURNAL FREE ACCESS

Download PDF (263K)
Uber die Konstitution des Hypognavins

Shinichiro Sakai

1958 Volume 6 Issue 4 Pages 448-450
Published: August 15, 1958
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.6.448

JOURNAL FREE ACCESS

Download PDF (381K)

Register with J-STAGE for free!