Catalytic, biological and DNA binding studies of organotin(IV) carboxylates of 3-(2-fluorophenyl)-2-methylacrylic acid: Synthesis, spectroscopic characterization and X-ray structure analysis

A new series of organotin(IV) carboxylates [Me2SnL2] (1), [Bu2SnL2] (2), [Oct2SnL2] (3), [Me3SnL] (4), [Bu3SnL] (5) and [Ph3SnL] (6), where L = 3-(2-fluorophenyl)-2-methylacrylate have been synthesized and characterized by FT-IR, CHNS and NMR (1H, 13C). The crystal structures of complexes (1) and (4) were also analyzed by single crystal X-ray analysis. The complex (1) adopted distorted octahedral geometry while complex (4) exhibited distorted trigonal bipyramidal geometry. The catalytic activity of the complexes was assessed in the production of biodiesel. Biodiesel is the monoalkyl ester of long chain fatty acids derived from the renewable feed stock, such as vegetable oil and is produced by a transesterification of vegetable oil with methanol. The results revealed that triorganotin(IV) complexes showed better catalytic activity than their diorganotin(IV) analogues. The complexes were also screened for their biological activities such as antibacterial, antifungal and cytotoxicity. The complexes 4–6 showed significant activity than the complexes 1–3. DNA interactions studies of ligand and complexes were investigated by UV–Vis absorption spectroscopy. The results showed that both ligand and complexes interact with DNA via intercalation as well as minor groove binding.

Graphical abstractSix new organotin(IV) carboxylates of the type R4−nSnLn where R = Me, n-Bu, Ph, L = 3-(2-fluorophenyl)-2-methylacrylate and n = 1 or 2, were synthesized and characterized by FT-IR, CHNS, NMR (1H, 13C) and single X-ray crystal analysis. The catalytic activity of the complexes was assessed in transesterification of triglycerides (vegetable oil) into fatty acid methyl esters (biodiesel). The complexes were screened for their anti-bacterial, anti-fungal and cytoxicity. DNA interaction studies were also performed using UV–Vis spectrophotometer to find out drug–DNA mechanism.Figure optionsDownload full-size imageDownload as PowerPoint slide