Design, synthesis and biological evaluation of organotin(IV) complexes of flumequine and cetirizine

Abstract

Six new organotin(IV) derivatives [Me 3 SnL 1 ] (1), [Bu 3 SnL 1 ] (2), [Ph 3 SnL 1 ] (3), [Me 3 SnL 2 ] (4), [Bu 3 SnL 2 ] (5) and [Ph 3 SnL 2 ] (6) (where HL 1 = = 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid (flumequine) and HL 2 = 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy] acetic acid (cetirizine)) were synthesized and characterized by elemental analysis, FT-IR spectroscopy, multinuclear 1 H-, 13 C-and 119 Sn-NMR, mass spectrometry and thermal analysis techniques. The obtained data reveal trigonal-bipyramidal geometry in case of complexes 1, 2, 4 and 5, and tetrahedral geometry for complexes 3 and 6 around the tin atom, whereas in complexes 3 and 6 the carboxylate ligand act as monodentate ligand through one of its oxygen atoms while it acts as bidentate ligand through two oxygen atoms for complexes 1, 2, 4 and 5. The antibacterial and antifungal efficacies of complexes 1-6 were assessed and the majority of the compounds showed good activities. The present research showed that the trimethyltin(IV) derivatives were particularly more effective than tributyltin(IV) and triphenyltin(IV) derivatives against all the bacterial and fungal strains. Antioxidant and DNA binding studies were also performed and promising results were obtained.

New triorganotin(IV) complexes of quinolone antibacterial drug sparfloxacin: Synthesis, structural characterization, DFT studies and biological activity

“…The organotin(IV) complexes with active drugs as ligands have emerged as an approach to prepare compounds with better or different pharmacological profile than that of the free ligand, as the biological activity of the organic drug can be enhanced by masking it upon coordination to an organotin(IV) moiety . In recent years, the extensive investigations on organotin(IV)‐drug system have resulted in organotin(IV) complexes with diverse range of active drugs having hetero donor atoms (N/O/S) . A few among these triorganotin(IV) complexes have exhibited good in vitro antituberculosis, antiproliferative, antimicrobial, and antioxidant activities.…”

“…In recent years, the extensive investigations on organotin(IV)‐drug system have resulted in organotin(IV) complexes with diverse range of active drugs having hetero donor atoms (N/O/S) . A few among these triorganotin(IV) complexes have exhibited good in vitro antituberculosis, antiproliferative, antimicrobial, and antioxidant activities. Most significantly, the triphenyltin(IV) complexes of meclofenamic acid, mefenamic acid and flufenamic acid have been reported to exhibit promising antimycobacterial activity against Mycobacterium tuberculosis H37Rv, and anticancer activity more potent than cis‐ platin against several human cancer cell lines .…”

“…Most significantly, the triphenyltin(IV) complexes of meclofenamic acid, mefenamic acid and flufenamic acid have been reported to exhibit promising antimycobacterial activity against Mycobacterium tuberculosis H37Rv, and anticancer activity more potent than cis‐ platin against several human cancer cell lines . Furthermore, recently a few studies have significantly highlighted the DNA binding, plasmid cleavage and enzyme inhibition studies on several triorganotin(IV) complexes of drugs.…”

Synthesis and Biological Activities of Organotin (IV) Carboxylates: A Review

“…26 For a high anti-fungal activity the total number of carbon atoms in the alkyl groups of a tri alkyltin compound should be about 9-12. 28 Organotin(IV) carboxylates have been used in silicone curing, 29 formation of polyurethane, 30 antifouling paints 31 and PVC stabilization. [32][33][34] Organotin(IV) carboxylates possess significant properties as antibacterial and antifungal agents and also as antitumor and anticancer drugs.…”

Interaction of triorganotin(IV) moiety with quinolone antibacterial drug ciprofloxacin: Synthesis, spectroscopic investigation, electronic structure calculation, and biological evaluation

“…In the last two decades, the extensive investigations on organotin(IV)‐drug system have been carried out with diverse range of active drugs having hetero donor atoms (N/O/S) . A few among these organotin(IV) complexes have been reported to exhibit good in vitro anticancer, antioxidant, antiproliferative, antituberculosis, and antiviral activities.…”