Routes to drug design via bioisosterism of carboxyl and sulfonamide groups

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19 Citations (Scopus)

Abstract

Aim: The similarity in the biological function of the bioisosteric pair, carboxyl and sulfonamide functional groups, is studied using the quantitative tool, average electron density of the bioisosteric moiety in drug molecules and the qualitative tool, electrostatic potential. Results/methodology: Five different capping groups (methyl, phenyl, chlorine, hydrogen and amine) were considered to investigate the effect of the environment on the properties of the bioisosteres. The molecules were considered in their neutral and anionic forms to account for the change in pH depending on the medium of the drug-receptor interactions. Conclusion: The new developed approach, average electron density, is not only advantageous as a qualitative descriptor, it is also more consistent compared with the conventionally accepted method, electrostatic potential, especially for the anions.

Original languageEnglish
Pages (from-to)2167-2180
Number of pages14
JournalFuture Medicinal Chemistry
Volume9
Issue number18
DOIs
Publication statusPublished - Dec 2017
Externally publishedYes

Keywords

  • average electron density through the quantum theory of atoms in molecules
  • bioisosteres
  • carboxyl and sulfonamide
  • electrostatic potential of neutral and anionic molecules in drug design

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmacology
  • Drug Discovery

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