Synthesis of Glibenclamide-Pregnenolone Conjugate and Its Relationship with Physico-chemical Descriptors log P, p, Rm, Vm, Pc and St
Corresponding Author(s) : Lauro Figueroa-Valverde
Asian Journal of Chemistry,
Vol. 23 No. 9 (2011): Vol 23 Issue 9
Abstract
In this study, a glibenclamide-pregnenolone conjugate was synthesized. The route involved a reaction of substitution of chloride atom involved in the chemical structure of glibenclamide to form the compound 2 using sodium hydroxide. Additionally, the compound 2 was bound to pregnenolone succinate to form the glibenclamide-pregnenolone conjugate (4) in the presence of dicyclohexylcarbodiimide and p-toluene sulfonic acid. To delineate the structural chemical requirements of the compounds 2 and 4, some parameters such as the physico-chemical descriptors log P, p, Rm, Vm, Pc and St were calculated. The results showed an increase in log P, p, Rm, Vm, Pc values for 4 in comparison with compound 2. These data indicate that steric impediment, conformational preferences and internal rotation of compound 4 could influence the degree of lipophilicity of this compound.
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