Exploring Cinnamic Acid Multitarget Hybrids in Terms of 2D-QSAR

Abstract

Cinnamic acids hybrids present a variety of significant biological activities and are characterized as pleiotropic agents. The 2D- QSAR analysis presented here attempts to identify the structural features and physicochemical properties of cinnamic acids hybrids presenting: a) antitumor activity; b) immunosuppressive activity; c) inhibitory activity on various enzymes; d) antioxidant activity. A 2D-QSAR analysis was carried out for 26 data sets of compounds taken from the literature using the C-QSAR program of Biobyte. In 5 cases hydrophobicity appeared to be important. Steric factors in the form of overall molar refractivity (CMR), molar refractivity of the substituents (MR), molar volume (MgVol) and the Verloop Sterimol parameters have a significant impact on the biological activity whereas electronic parameters as Hammett σp, σm, σo or Σσ appear in most of the cases. The anticancer as well as anti-inflammatory and antioxidant activities of caffeic acid hybrids are governed by lipophilicity, electron and stereochemical factors.