4-Chloro-2-(5,6-dihydro-benzo[4,5]imidazo[1,2-c]quinazolin-6-yl)-phenol (HL); synthesis, characterization, crystal structure, Hirshfeld surface analysis and BSA binding studies

Abstract

A new asymmetric bidentate Schiff-base molecule 4-Chloro-2-(5,6-dihydro-benzo[4,5]imidazo[1,2-c]quinazolin-6-yl)-phenol (HL), has been synthesized and characterized using physicochemical and spectroscopic techniques, single crystal X-ray diffraction and Hirshfeld surface analysis. Crystal structure analysis reveals that the compound crystallized in the orthorhombic system in the Pbca space group. The in vitro interactions of the synthesized compound, with bovine serum albumin was thoroughly investigated using UV–Vis absorption in combination with fluorescence quenching techniques, and these methods were used to determine the binding parameters also the mechanism of interaction behind the new compound HL bound to BSA. Values of the binding constants (Kb) were about ∼105 M−1 signifying a moderate interaction between HL and BSA making the protein suitable for transportation and delivery of the compound. Thermodynamic parameters also revealed binding through weak van der Waals forces and hydrogen bonding interactions of HL to BSA. The results obtained from docking studies were consistent and complemented those derived from other experimental studies.