Organotin(IV) derivatives of amide-based carboxylates: Synthesis, spectroscopic characterization, single crystal studies and antimicrobial, antioxidant, cytotoxic, anti-leishmanial, hemolytic, noncancerous, anticancer activities

Abstract

Four new triorganotin(IV) amide based carboxylates of general formula R3SnL1and R3SnL2, where R = Me(1,3) and n-butyl (2,4), and L1= (Z)-4-(p-methoxyphenylamino)-4-oxo-2-butenoic acid (HL1) L2 = (Z)-4-(3,5-bis(trifluoromethyl)phenylamino)-4-oxo-2-butenoic acid (HL2) have been synthesized by refluxing methanolic solution of organtin(IV) chloride and ligand (1:1 M ratio). The synthesized compounds were characterized by FT-IR, elemental analysis, NMR (1H, 13C, 119Sn &19F) and single crystal X-ray crystallography. The ligands coordinate to tin atom through oxygens (carboxylate and amide) showing distorted trigonal bipyramidal geometry with polymeric bridging behavior in solid state. However, the geometry is switched over from trigonal bipyramidal to tetrahedral upon dissolution as confirmed by multinuclear (1H, 13C, 19F and 119Sn) NMR. The prepared ligands and compounds 1–4 were screened for antimicrobial, antioxidant, cytotoxicity, hemolysis, antileishmanial and anticancer and noncancerous activities. The results showed significant antimicrobial activities, antioxidant, good cytotoxic LD50 values, percent hemolytic values, antileishmanial and anti-cancer activities. Compound 2 and 4 were found the most active antileishmanial and anticancer agent, respectively.