Structure-activity relationships of benzimidazole carbamates as inhibitors of mammalian tubulin, in vitro

Biochem Pharmacol. 1985 Apr 1;34(7):1073-7. doi: 10.1016/0006-2952(85)90611-2.

Abstract

The structure-activity relationships of thirty-two methyl (5(6)-substituted benzimidazol-2yl) carbamates as inhibitors of the rate of polymerisation of mammalian tubulin have been investigated. The size or some colinear physico-chemical characteristic of the substituent in the 5 (or 6)-position has a profound effect on potency. The presence of branching with or without a commensurate increase in the polarity of the 5(6)-substituent adjacent to the benzimidazole ring (alpha-position) resulted in a loss of activity. The nature of the overall site, as reflected by the quantitative models, could relate to either the hydrophobicity or molar volume of the 5 (or 6)-substituents.

MeSH terms

  • Animals
  • Anthelmintics / pharmacology*
  • Antifungal Agents / pharmacology*
  • Benzimidazoles / pharmacology*
  • Dose-Response Relationship, Drug
  • In Vitro Techniques
  • Models, Biological
  • Structure-Activity Relationship
  • Tubulin Modulators*

Substances

  • Anthelmintics
  • Antifungal Agents
  • Benzimidazoles
  • Tubulin Modulators