Russian Journal of Organic Chemistry

, Volume 50, Issue 11, pp 1667–1676 | Cite as

The synthesis of isoxazolyl- and isothiazolylcarbamides exhibiting antitumor activity

  • V. I. Potkin
  • S. K. Petkevich
  • A. V. Kletskov
  • Yu. S. Zubenko
  • P. V. Kurman
  • S. G. Pashkevich
  • T. A. Gurinovich
  • V. A. Kulchitskiy
Article

Abstract

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.

Keywords

Azide Carbamate Isoxazole Anhydrous Methanol Isothiazole 

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Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  • V. I. Potkin
    • 1
  • S. K. Petkevich
    • 1
  • A. V. Kletskov
    • 1
  • Yu. S. Zubenko
    • 1
  • P. V. Kurman
    • 2
  • S. G. Pashkevich
    • 3
  • T. A. Gurinovich
    • 3
  • V. A. Kulchitskiy
    • 3
  1. 1.Institute of Physical Organics Chemistry of National Academy of Sciences of BelarusMinskBelarus
  2. 2.Institute of Bioorganic Chemistry of National Academy of Sciences of BelarusMinskBelarus
  3. 3.Institute of Physiology of National Academy of Sciences of BelarusMinskBelarus

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