Synthesis, spectral- and theoretical study, x-ray analysis, and antiproliferative activity of 4,5-dihydrobenzoferroceno[1,2-d][1,2,3] selenadiazole and its benzo-fused analogue

Synthesis, structure determination, and in vitro antiproliferative effect of 4,5-dihydronaphto[1,2-d][1,2,3] selenadiazole (1) and 4,5-dihydrobenzoferroceno[1,2-d][1,2,3] selenadiazole (2) are presented. The synthesized molecules were characterized by NMR, IR, Raman, mass, and UV spectroscopies. The equilibrium structures of 1 and 2 were calculated using the B3LYP/6-31thornG* quantum-chemical method, and the solid phase structure of 2 was determined by single crystal X-ray diffraction. The antiproliferative effect of 1 and 2 was investigated against three tumorous human cell lines. Both compounds were active against cervical HeLa and ovarian A2780 cell lines, and 2 was also active against breast MDA-MB-231 cell growth. The ferrocene derivative 2 was found to be more effective than its organic analogue 1. (c) 2018 Elsevier B.V. All rights reserved.