An efficient approach towards the synthesis, crystal structures, DFT and cytotoxic activity of highly congested 11-aryl-10,12-dihydrodiindino[1,2-b′,2′,1′-e]pyridine

Abstract

An efficient and novel method for the synthesis of a series of 11-aryl-10,12-dihydrodiindino[1,2-b′,2′,1′-e]pyridine via one-pot multi-component reactions of aldehydes, indan-1-one and ammonium acetate has been delineated. All prepared compounds were structurally elucidated by IR, UV-Vis, 1H and 13C NMR and X-ray diffraction techniques. The molecules adopted monoclinic crystal system with P21/c space group and almost similar unit cell dimensions. The X-ray molecular geometries of the studied compounds were in excellent agreement with those computed by B3LYP/6-311++G(d,p) level of theory. The energies of the frontier orbitals calculated by B3LYP/6-311++G(d,p) level of theory enabled monitoring the reactivity and stability of the title molecules. The non-linear optical properties (NLO) and pNA were also computed and discussed. Compounds have shown broad spectrum cytotoxic activity against some human tumour cell lines; two of them rendering the most profound effect.