Synthesis, Electronic, Spectroscopic and Molecular Structure Investigation on Anticancer Drug Spirooxindole-Chromene Derivative

This work explores carbon-carbon bond formation via Michael addition in synthesizing a novel spirooxindole-chromene derivative (4) using click chemistry, examining its quantum parameters and potential anticancer effects. Spectroscopic methods, including UV-800, FT-IR and NMR, were used alongside quantum calculations (IEFPCM model) to validate the molecular structure. The compound was optimized in the gas phase with a 6-311++G(d,p) basis set and VEDA was employed for vibrational assignments. Drug-likeness properties were assessed using the ADMET online tool. In vitro studies with sixty human cancer cell lines indicated that compound 4 showed 17.88% resistance against UO-31 renal cancer cells at 10–5 M. Virtual screening identified active sites related to anticancer proteins 4DRI, 6CZ4 and 8BR9, with binding energies of -7.76, -7.3 and -6.59 kcal/mol, respectively. Ramachandran plots indicated favourable conformations for docking, with blue areas representing optimal binding positions. Ultimately, compound 4 may be enhanced for anticancer efficacy through elimination reactions at its primary amine position on the pyrano ring.