Carbonic anhydrase inhibitors — Part 47: Quantum chemical quantitative structure-activity relationships for a group of sulfanilamide Schiff base inhibitors of carbonic anhydrase

Supuran, C.T. and Clare, B.W. (1998) Carbonic anhydrase inhibitors — Part 47: Quantum chemical quantitative structure-activity relationships for a group of sulfanilamide Schiff base inhibitors of carbonic anhydrase. European Journal of Medicinal Chemistry, 33 (6). pp. 489-500.

Abstract

A series of sulfanilamide Schiff base inhibitors of CA I and CA II have been studied by the semi-empirical AM1 method. The charges on the atoms of the sulfonamide group, and the dipole moment, have been calculated by four methods: a standard vacuum calculation, a solution calculation by the COSMO method, a solution calculation with, in addition, the charges and dipole moments calculated by fitting to the calculated electrostatic potential, and a calculation by the older CNDO method. The data were subjected to a classical multiple regression analysis with care to avoid the possibility of chance correlation or collinearity. The ACE technique was also used to allow for nonlinearity. A number of statistically significant equations were derived, which were mostly consistent with previous studies. While the ESP-based charges gave the best equations, the improvement was not sufficient to convincingly exclude the other methods. This is the first study which evidenced by means of QSAR calculations isozyme-specific features of the two isozymes CA I and CA II, in their interaction with sulfonamide inhibitors.

Item Type:	Journal Article
Publisher:	Elsevier Masson SAS
Copyright:	© Elsevier, Paris
URI:	http://researchrepository.murdoch.edu.au/id/eprint/36635

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