SYNTHESIS, STRUCTURE AND BINDING AFFINITY OF A NOVEL 1,2,3-TRIAZOLYL-CARVONE WITH BOVINE SERUM ALBUMIN

Abstract

On the basis of natural L-carvone monoterpenoide, a method for the synthesis of (5R)-2-methyl-5-(3-{4-[(azepan-1-yl)methyl]-1H-1,2,3-triazol-1-yl}prop-1-en-2-yl)cyclohex-2-en-1-one has been developed. The reaction conditions providing high yields of the target products were optimized. The structure of the synthesized compound has been confirmed and the physicochemical constants have been determined. The nature of the interaction and the thermodynamic characteristics of the 1,2,3-triazolyl-carvone with serum albumin (BSA) have been also determined. It has been shown that hydrophobic interactions are the predominant intermolecular forces stabilizing 1,2,3-triazolyl-carvone–BSA system. The distance between donor (BSA) and acceptor (1,2,3-triazolyl-carvone) has been calculated using Förster’s fluorescence energy transfer theory.