The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

Abstract

The present study examines a series of six biologically-active flavonoid and chromanone derivatives by X-ray crystal structure analysis: (E)-3-benzylidene-2-phenylchroman-4-one, C₂₂H₁₆O₂, I, (E)-3-(4-methylbenzylidene)-2-phenylchroman-4-one, C₂₃H₁₈O₂, II, (E)-3-(3-methylbenzylidene)-2-phenylchroman-4-one, C₂₃H₁₈O₂, III, (E)-3-(4-methoxybenzylidene)-2-phenylchroman-4-one, C₂₃H₁₈O₃, IV, (E)-3-benzylidenechroman-4-one, C₁₆H₁₂O₂, V, and (E)-3-(4-methoxybenzylidene)chroman-4-one, C₁₇H₁₄O₃, VI. The cytotoxic activities of the presented crystal structures have been determined, together with their intermolecular interaction preferences and Hirshfeld surface characteristics. An inverse relationship was found between the contribution of C...C close contacts to the Hirshfeld surface and cytotoxic activity against the WM-115 cancer line. Dependence was also observed between the logP value and the percentage contribution of C...H contacts to the Hirshfeld surface.

Keywords: Hirshfeld analysis; QSAR; chromanone; crystal structure; cytotoxic activity; flavanoid.