Diorganotin(IV) complexes with 2-furancarboxylic acid hydrazone derivative of benzoylacetone: Synthesis, X-ray structure, antibacterial activity, DNA cleavage and molecular docking

•Synthesis of two diorganotin complexes with a hydrazone derived from diketone.•Hydrazone undergoes a ring opening reaction and act as a tridentate ligand.•Coordination number of tin is five and geometry is between square-pyramidal and trigonal-bipyramidal.•The diphenyltin(IV) complex exhibited good antibacterial activitiy.•The DNA cleavage activity and molecular docking of compounds has been studied.

Two new diorganotin(IV) complexes, Me2SnL and Ph2SnL, have been synthesized from the reaction of Me2SnCl2 and Ph2SnCl2 with the hydrazone H2L [H2L = (Furan-2-yl) (5-hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-methanone] derived from furan-2-carbohydrazide and benzoylacetone. The new compounds have been characterized by elemental and spectroscopic analyses. The crystal structures of the monohydrate form of the ligand and of the Me2SnL derivative have been also determined by X-ray crystallography. Experimental evidences confirm the existence of the hydrazone ligand exclusively in cyclic form in both solution and solid state. On coordination to tin the hydrazone undergoes a ring opening reaction and a doubly deprotonation to act as a tridentate ligand via imine nitrogen and enolic oxygens. The tin atom in the complexes is five coordinate with geometry between square-pyramidal and trigonal-bipyramidal. The in vitro antibacterial activity of ligand and its complexes has been evaluated against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria. The interaction between compounds with bacterial DNA was also studied by molecular docking. Our findings indicate that diphenyltin(IV) complex, by binding to DNA via minor groove to TATA sequence in genes upstream, has good activities along with the standard antibacterial drugs. Our agarose-gel electrophoresis experiments show that the ligand exert DNA cleavage, while Me2SnL and Ph2SnL did not.

Graphical abstractTwo new diorganotin(IV) complexes have been synthesized with a hydrazone derived from furan-2-carbohydrazide and benzoylacetone and characterized both in solid and solution. Antibacterial activity, DNA cleavage and molecular docking have been studied. R2SnCl2 (R = Me, Ph) + H2L + 2NEt3 → R2SnL + 2NHEt3.Figure optionsDownload full-size imageDownload as PowerPoint slide