Novel Ferrocenyl‐azole Derivatives: Synthesis, DFT Calculation and Unlocking the Anticancer Potential

Abstract

Herein, a series of novel ferrocenyl/phenyl/thiophenyl‐azoles was disclosed by vinylic amination of ferrocenyl/phenyl/thiophenyl substituted β‐chloro cinnamaldehydes and acrylonitriles. A highly economical and robust chalcogen‐stabilized iron selenide carbonyl cluster Fe3Se2(CO)9 worked as an efficient catalyst under aerobic conditions. The amination of ferrocenyl/phenyl/thiophenyl substituted β‐chloro‐vinylic Csp2‐Cl with azole derivatives was fully established and fabrication of the Csp2‐N bond was completely supported by various spectral analysis. Moreover, wide range of substrates with functionally different azoles were investigated for the present reaction and good to excellent transformation was recorded. Some of the selected ferrocenated azole derivatives were screened for anti‐cancer activity against the prostate cancer cells (PC‐3) and found to be highly active at low concentration of 5.77µM with IC50 value. Furthermore, HOMO and LUMO levels and energy gap of some selected compounds were calculated by the density functional theory (DFT).