Chemical and Pharmaceutical Bulletin

Studies on Compounds related to Pyrazine. III. Synthesis of 2-Substituted Thiazolo [b] quinoxaline.

Haruo Saikachi, Shoichiro Tagami

1961 Volume 9 Issue 12 Pages 941-944
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.941

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2-Amino-3-mercaptoquinoxaline was prepared by the reaction of 2-amino-3-chloroquinoxaline with thiourea or potassium hydrogensulfide, 2-amino-3-hydroxyquinoxaline with phosphorus pentasulfide, or 2, 3-dimercaptoquinoxaline with ammonia. 2-Substituted thiazolo [b] quinoxaline was prepared by boiling 2-amino-3-mercaptoquinoxaline with excess of acid anhydride or by heating with excess of acid chloride in pyridine.

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Reaction of Amide Homologs. V. Acetamidomethylation of Phenol and Anisole with N, N'-Methylenediacetamide.

Minoru Sekiya, Noboru Yanaihara, Toshio Masui

1961 Volume 9 Issue 12 Pages 945-948
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.945

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Acetamidomethylation of phenol and anisole was carried out by heating with N, N'-methylenediacetamide and phosphoryl chloride. Formation of N-(2-and 4-hydroxybenzyl) acetamides resulted in the case of phenol and formation of N-(4-methylbenzyl) acetamide in the case of anisole.

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Spectrophotometric Studies on Organic Substances. IX. Ultraviolet Absorption Spectra of Derivatives of Heterocyclic N-Oxides. General Properties on the Solvent Effect and the Substituting Effect.

Tanekazu Kubota, Hiroshi Miyazaki

1961 Volume 9 Issue 12 Pages 948-961
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.948

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Ultraviolet absorption spectra and fluorescence spectra of many derivatives of benzene and naphthalene heterocyclic N-oxides and a few derivatives of anthracene and phenanthrene heterocyclic N-oxides were recorded in various solvents. Experimental results were discussed from the point of solvent effect and substituting effect. Ultraviolet spectra of all N-oxides used showed increasing blue shift with increasing polarity of the solvent. These results agreed well wlth the behavior in the solvent effect which was reported in previous papers for basic heterocyclic N-oxides and their simple derivatives. It is suggested that this solvent effect is a general property for heterocyclic N-oxides. As for the fluorescence spectra of N-oxides, such a general property as was observed on ultraviolet spectra was not observed. A main reason for this solvent effect is attributed to hydrogen bonding such as &egs;N→O&egs;H (in solvent). On the other hand, a relationship was found to exist between the effect of substituting positions and the spectra. By arranging many substituents in the order of substituting ability and classifying the positions in a molecule belonging to two ring systems into two classes, it has been found that the above relationship is present between ¹L_b and ¹L_a absorption bands. This property may also be considered as a general property.

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Studies on the Metabolism of Naturally Occurring Anthraquinones. I. The Metabolism of 1-Hydroxyanthraquinone and 2-Hydroxyanthraquinone.

Mitiiti Fujita, Tsutomu Furuya, Mitsuyoshi Matsuo

1961 Volume 9 Issue 12 Pages 962-966
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.962

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The metabolic fate of 1-hydroxy-and 2-hydroxyanthraquinone in rat has been elucidated. Both the compounds were mainly hydroxylated to alizarin. Appearance of two or more hydroxylated anthraquinones was not detected. The urinary and fecal metabolites were determined directly by a densitometer.

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Studies on the Metabolism of Naturally Occurring Anthraquinones. II. The Metabolism of 1-Methoxyanthraquinone and 2-Methoxyanthraquinone.

Mitiiti Fujita, Tsutomu Furuya, Mitsuyoshi Matsuo

1961 Volume 9 Issue 12 Pages 967-970
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.967

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Each of 1-methoxy-and 2-methoxyanthraquinones was demethylated in rats to be metabolized to the 1-hydroxy compound and they were finally hydroxylated to alizarin. Every form in conjugation of their metabolites was determined using a densitometer and an ultraviolet spectrophotometer.

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Studies on the Synthetic Analgesics. XVI. Synthesis of 1-(2-tert-Aminoalkyl)-3, 4-dihydrocarbostyrils.

Noboru Shigematsu

1961 Volume 9 Issue 12 Pages 970-975
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.970

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As a part of studies on nonnarcotic antipyretic-analgesic, 1-(2-tert-aminoalkyl)-3, 4-dihydrocarbostyril (III : R'=H), 1-(2-tert-aminoalkyl)-6-hydroxy-3, 4-dihydrocarbostyril (III : R'=6-OH), and 1-(2-tert-aminoalkyl)-7-hydroxy-3, 4-dihydrocarbostyril (III : R'=7-OH) were synthesized. Analgesic, antitussive, and antipyretic action of these compounds were examined and some of these compounds showed anticipated activity.

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Studies on Acetylenic Compounds. XIX. A New Method for Synthesis of DL-Arabinose.

Issei Iwai, Kazuo Tomita

1961 Volume 9 Issue 12 Pages 976-979
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.976

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DL-Arabinose was stereospecifically synthesized starting from 5-ethoxy-4-penten-2-yn-1-ol, which was prepared by the Grignard reaction of formaldehyde with 4-ethoxy-3-buten-1-yn-1-yl magnesium bromide.

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Synthetic Approaches to Calycanthaceae Alkaloids. II. A Synthesis of 1, 1'-Dimethyl-3, 3'-bis (2-aminoethyl)-3, 3'-bioxindole.

Tohru Hino

1961 Volume 9 Issue 12 Pages 979-988
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.979

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Alkylation of 1, 1'-dimethyl-3, 3'-bioxindole (V) was carried out. A higher-melting isomer (VIIa) was obtained by dimethylation of (V) with sodium hydride in benzene. while a lower-melting isomer (VIIb) was obtained by dimethylation of (V) with sodium amide in liquid ammonia. Cyanomethylation of (V) with sodium hydride in benzene afforded (VIIIa), which was further cyanomethylated by chloroacetonitrile with potassium carbonate, sodium iodide, and acetone to give (IX), which was also obtained by direct biscyanomethylation with the latter reagents. Two other 3, 3'-disubstituted 3, 3'-bioxindoles (X, XII) were also prepared by analogous alkylation. The compound (III), which was considered to be an attractive intermediate for the synthesis of (I) and (II), was obtained by catalytic reduction of (IX).

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Synthetic Approaches to Calycanthaceae Alkaloids. III. Reductive Cyclization of 3, 3'-Bioxindoles. (1). A Formation of 5, 7-Dimethyl-11b, 11c-bis (2-dimethylaminoethyl)-5, 5a, 6a, 7, 11b, 11c-hexahydrofuro [2, 3-b : 5, 4-b'] diindole.

Tohru Hino

1961 Volume 9 Issue 12 Pages 988-995
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.988

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The Ladenburg reduction and lithium aluminium hydride reduction of 3, 3'-disubstituted 3, 3'-bioxindole were carried out. By the former method, (I) and (II) gave 1, 3-dimethylindole and 1-methyl-3-(2-aminoethyl) indole respectively, while by the latter method, (I) gave furo [2, 3-b : 5, 4-b'] diindoles (XVIII, XXV). The compound (XXVII), which has the same planar structure as the product (XIX) obtained from folicanthine, was obtained by the lithium aluminium hydride reduction of (III).

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Studies on Carcinostatic Substances. XXXVIII. Chemical and Antitumor Properties of Monofunctional Derivatives of Nitrogen Mustard.

Kenichi Sawatari

1961 Volume 9 Issue 12 Pages 996-999
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.996

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Supported by the fact that N-methyl-N-2-chloroethyl-3-chloropropylamine exhibited a strong antitumor effect on Yoshida sarcoma or series of rat ascites hepatomas, eight derivatives of nitrogen mustard were newly synthesized, which have only one but highly reactive 2-chloroethyl group in a molecule. Antitumor test of these compounds on Yoshida sarcoma was, however, negative.

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Organic Phosphates. XVIII. Syntheses of Lyxouridine 2', 3'-Cyclic Phosphate and Related Compounds.

Tyunosin Ukita, Hikoya Hayatsu

1961 Volume 9 Issue 12 Pages 1000-1005
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.1000

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Lyxouridine 2', 3'-cyclic phosphate (III), which is a stereoisomer of uridine 2', 3'-cyclic phosphate, a natural substrate of bovine pancreatic ribonuclease, was synthesized. The structure of (III) was verified by its comparison with lyxouridine 3', 5'-(VII) and 2', 5'-cyclic phosphate (VIII) synthesized via lyxouridine 5'-phosphate (VI).

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Studies on Saponin-bearing Drugs. III. Sapogenins of Domestic Senega and Polygala, a Chinese Drug"Yuan chi"( ?? ?? ).

Mitiiti Fujita, Hideji Itokawa

1961 Volume 9 Issue 12 Pages 1006-1008
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.1006

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Comparative studies were made on the chemical nature of the sapogenins obtained by hydrolysis of two kinds of the saponins isolated from the roots of Polygala senega var. latifolia et P. tenuifolia. As the results, it was confirmed that the sapogenin of the former is completely identical with that of the latter and it is possible consider that both the compounds are the same as one of those obtained by Tschesche and Gupta from a Polygalaceous plant, Bredemeyera floribunda.

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Cinnoline Chemistry. VIII. α-(ω-Dialkylaminoalkyl)-α-phenyl-4-cinnolineacetonitriles and Related Compounds.

RaymondN. Castle, Masayuki Onda

1961 Volume 9 Issue 12 Pages 1008-1011
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.1008

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Five new (ω-dialkylaminoalkyl) phenylacetonitriles were prepared and these and other similar nitriles were condensed with 4-chlorocinnoline in the presence of sodium amide to produce seven new α-(ω-dialkylaminoalkyl)-α-phenyl-4-cinnolineacetonitriles. All of these condensed nitriles were hydrolyzed and decarboxylated to seven new 4-[(1-phenyl-ω-dialkylamino) alkyl] cinnolines. These latter two classess of compounds were prepared for pharmacological screening.

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Metabolism of Lipoamide and Lipoic Acid in Rabbits

Fumihiko Tanaka, Shigeru Shintani, Momoyoshi Nakamura, Iwao Nakayama

1961 Volume 9 Issue 12 Pages 1012-1014
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.1012

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Absolute Configuration of Cycloheximide

Tomoharu Okuda, Makoto Suzuki

1961 Volume 9 Issue 12 Pages 1014-1016
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.1014

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Reaction of Dehydroacetic Acid under a Mild Condition

Sadao Iguchi, Atsuko Inoue, Chieko Kurahashi

1961 Volume 9 Issue 12 Pages 1016-1017
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.1016

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Separation and Structure of 3-Methylpyridazine 1-Oxide and 2-Oxide

Hideo Kano, Masaru Ogata, Haruyuki Watanabe, Ichiro Ishizuka

1961 Volume 9 Issue 12 Pages 1017-1020
Published: December 25, 1961
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.9.1017

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