Abstract
The synthesis of the benzoimidazolyl-ferrocene containing compound was achieved by Knovenagel condensation of ferrocene-1-carbaldehyde and (2-benzoimidazolyl) acetonitrile. Single crystal structure of the compound showed intramolecular (hydrogen bonding) NH center dot center dot center dot N interactions, forming an infinite 1D-chain that propagate along the [010] direction. The titled compound exhibits two major energy bands around 360 nm and 515 nm in the UV-vis range, that are assigned by TD-DFT calculations for CT (Donor-pi-Acceptor) and MLCT respectively. In acidified solution, the molecule spectrum exhibits a red shift in the lowest energy band associated with a color change from purple to violet when the pH maintained around 5. DNA-binding study showed hypochromic shifts in all the absorption with no red shift in the MLCT which can attributed to the reduced probability of the transitions as the LUMO is strongly involved in the interaction with the ct-DNA. The compound exerts high toxicity against the lung cancer cell line (A549) while the prostate cancer cell line (PC-3) was extremely resistant. Docking study showed that the compound and Erlotinib have similarities in targeting the EGFR. Theoretically, the title compound exhibits physiochemical features, matching those of orally active drugs. Selective cytotoxicity of chemotherapeutic agents is desirable and hence more studies would be undertaken on benzoimidazolyl-ferrocene to understand the mechanism of action on the lung cancer cell line. (C) 2019 Elsevier B.V. All rights reserved.