Synthesis, chemical characterization, DNA interaction and antioxidant studies of ortho, meta and para fluoro substituted ferrocene incorporated selenoureas

Abstract

We have reported a one pot synthesis of three new ferrocene incorporated selenoureas namely; 1-(2-fluorobenzoyl)-3-(4-ferrocenyl-3-methylphenyl) selenourea (MeP2F), 1-(3-fluorobenzoyl)-3-(4-ferrocenyl-3-methylphenyl) selenourea (MeP3F) and 1-(4-fluorobenzoyl)-3-(4-ferrocenyl-3-methylphenyl) selenourea (MeP2F) by the reaction of corresponding carboxylic acid chlorides with potassium selenocyanate (KSeCN) and 3-methyl-4-ferrocenyl aniline in acetone under constant stirring. Synthesized compounds were characterized by FTIR, NMR (1H and 13C), CHNS and AAS. We have also presented X-rays single crystal structure for MeP2F. DNA binding studies were evaluated with the help of cyclic voltammetry in the presence of TBAP (tertiary butyl ammonium perchlorate) as supporting electrolyte in DMSO/water mixture of 70:30. Binding constant for MeP2F is 1.499 × 103 M -1, MeP3F is 1.706 × 103 M-1 and MeP4F is 1.035 × 103 M-1. Binding site size for MeP2F (0.334 bp) < MeP4F (0.410 bp)