Premium
Exploring Structural Requirements for Aldose‐Reductase Inhibition by 2,4‐Dioxo‐5‐(naphth‐2‐ylmethylene)‐3‐thiazolidinyl Acetic Acids and 2‐Thioxo Analogues: Fujita‐Ban and Hansch Approach
Author(s) -
Soni Love Kumar,
Kaskhedikar Satish G.
Publication year - 2006
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200500015
Subject(s) - aldose reductase , chemistry , aldehyde reductase , stereochemistry , fujita scale , acetic acid , quantitative structure–activity relationship , enzyme , biochemistry , physics , meteorology
Abstract A Quantitative Structure‐Activity Relationship (QSAR) study based on Fujita‐Ban and classical Hansch approach was performed on 2,4‐dioxo‐5‐(naphth‐2‐ylmethylene)‐3‐thiazolidinyl acetic acids and 2‐thioxo analogues to gain structural insight into the binding mode of the molecules to the aldose‐reductase enzyme. First, the Fujita‐Ban approach has been followed, which revealed the highest activity contribution for 2‐thioxo analogues of 3‐thiazolidinyl acetic acids as compared to 2,4‐dioxo analogues. Further, the Hansch approach confirms that 2‐thioxo‐4‐oxo‐3‐thiazolidinyl acetic acids are conducive to aldose‐reductase inhibitory activity. The hydrophobic properties of the various substituents have been found to play major roles in the binding of these compounds with the receptor.