A computational study of lipophilicity of E-2-arylmethylen-1-tetralones and their heteroanalogues using QSAR and DFT Based Molecular surface Electrostatic Potential

Document Type : Research Paper

Authors

1 Department of Applied Chemistry, Faculty of Pharmaceutical Chemistry, Pharmaceutical Siences Branch, Islamic Azad University, Tehran, Iran, (IAUPS)

2 Department of Chemistry, Sharif University of Technology, Tehran, Iran

3 Department of Chemistry, Payame Noor University, Tehran, Iran

Abstract

E-2-Arylmethylen-1- tetralones and E-3-phenylme thylene chromanone-4-ones and their derivatives closely related to flavonoids belong to the plant secondary metabolites most investigated recently.The class of flavonoids is an enormous class of plant secondary metabolites having so different pharmacological effects as inhibition of nitric oxide synthasecancer preventive effect or potential impact on the etiology of certain vascular disease.Numerous biological activity have been attributed to the tetralones mentioned. In this study B3P86/6-31++G* was used to compute and map the molecular surface electrostatic potentials of a group of tetralones and chromanones to identify common features related to their lipophilicity. Several statistical properties including potentials extrema (Vs,min, Vs,max), the average of positive electrostatic potential on the surface (Vst), the average of V(r), over the surface (Vs) and the variance of V(r) over the surface (62-) and system lipophilicity were computed. Statistically, the most significant correlation is a three parameter equation with correlation coefficient, R value of 0.881 and R2adj=0.743. The obtained models allowed us to reveal lipophilicity activity of tetralones.
Journal of Physical & Theoretical Chemistry
Volume 13, Issue 2
September 2016
Pages 171-177

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