Synthesis, structure elucidation and surface analysis of a new single crystal N-((2-(benzo [4,5]imidazo [1,2-c]quinazolin-6-yl)phenyl)carbamothioyl)heptanamide: Theoretical and experimental DNA binding studies

A new quinolinyl-thiourea hybrid 3, was synthesized by reacting 2-(benzo [4,5]imidazo [1,2-c]quinazolin-6-yl)aniline with heptanoyl isothiocyanate in excellent yield. Spectro-elemental characterizations and single-crystal X-ray analysis were done for the structure elucidation. Hirshfeld surface analysis of 3 was performed to determine the weak intermolecular interactions and intramolecular H-bonds in the crystal structure. The relative contributions of the main intermolecular contacts as well as the enrichment ratios derived from the Hirshfeld surface analysis establish the synthon 3 to be a molecule of significant structural and biological interest. HOMO - LUMO energy gap and electrostatic potential map were computed by DFT and the charge transfer regions within the molecule were identified for the possible electrophilic and nucleophilic attack. Molecular docking and UV–visible spectroscopic findings for DNA binding pointed towards the anticancer potential of 3. Further, viscosity measurements of DNA in the presence of compound’s concentrations verified a mixed binding mode for 3 - DNA interaction. A new single crystal N-((2-(benzo [4,5]imidazo [1,2-c]quinazolin-6-yl)phenyl) carbamothioyl)heptanamide: synthesis, X-ray, Hirshfeld, DFT and DNA binding studies. [Display omitted] •A new quinolinyl thiourea conjugate was designed and synthesized.•X-ray crystal structure determination.•Hirshfeld surface and DFT structure analysis.•Docking, spectroscopic and viscosity studies for DNA binding.