The synthesis of isoxazolyl- and isothiazolylcarbamides exhibiting antitumor activity

Accessible 5-phenyl( p -tolyl)isoxazol-3-carboxylic, 4,5-dichlorothiazol-3-carboxylic and 5-(benzylsulfanyl)-4-chlorothiazol-3-carboxylic acids were converted via a series of cascade transformations into the corresponding (1,2-azolyl)-3-carbonyl azides whose reaction with slightly basic aryl(heteryl...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2014-11, Vol.50 (11), p.1667-1676
Main Authors: Potkin, V. I., Petkevich, S. K., Kletskov, A. V., Zubenko, Yu. S., Kurman, P. V., Pashkevich, S. G., Gurinovich, T. A., Kulchitskiy, V. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Accessible 5-phenyl( p -tolyl)isoxazol-3-carboxylic, 4,5-dichlorothiazol-3-carboxylic and 5-(benzylsulfanyl)-4-chlorothiazol-3-carboxylic acids were converted via a series of cascade transformations into the corresponding (1,2-azolyl)-3-carbonyl azides whose reaction with slightly basic aryl(heteryl)amines led to generation of 1-(1,2-azolyl)-3-aryl(heteryl)carbamides. To obtain isoxazolyl(isothiazolyl)carbamides containing the residues of highly basic amines, (1,2-azolyl)-3-carbonyl azides were preliminary transformed into aryl (1,2-azol-3-yl)carbamates by the action of phenol or 4-fluorophenol. Carbamates then were introduced into reaction with aliphatic or heterocyclic amines. Some of the obtained compounds and their precursors show high antitumor activity and are capable to increase the effect of cytostatic drugs applied in the medical practice.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428014110219