Novel Organotin(IV) Complexes of 2-[4-Hydroxy-3-((2-hydroxyethylimino)methyl)phenylazo]benzoic Acid: Synthesis, Structure, Noncovalent Interactions and In Vitro Antibacterial Activity

Abstract

Three new organotin(IV) complexes, [Me3Sn(H2L)]2 (1), Bu3Sn(H2L) (2), and [(Bu2Sn(H2L))2O]2 (3) were synthesized by the reaction of 2-[4-hydroxy-3-((2-hydroxyethylimino)methyl)phenylazo]benzoic acid (H3L) with appropriate alkyltin(IV) precursors. The complexes were characterized by elemental analysis, IR, and multinuclear (1H, 13C and 119Sn) NMR spectroscopy. Further, the complex 1 was analyzed by single-crystal X-ray analysis. It displays a 24-membered cyclic dimeric Me3SnIV(H2L) unit where the ligand act as a bridging framework using its carboxylate-O and phenoxy-O atoms. The Sn(IV) adopts distorted trigonal-bipyramidal geometry. In the solution state, the structures were determined by 119Sn-NMR spectroscopy, and the complexes 1 and 2 have distorted tetrahedral geometry, whereas complex 3 shows distorted trigonal-bipyramidal geometry around the tin centres. The Hirshfeld surface analysis and DFT calculations, together with a topological analysis of the electron density distribution in the crystal structure of complex 1, indicate that its molecular packing determined by various noncovalent interactions, including stacking and hydrogen bonding. The antibacterial studies of the ligand and the complexes (1–3) against gram-negative bacteria viz. Klebsiella pneumoniae (A),Vibrio cholerae (M) and Shigella boydii (Q) and gram-positive bacteria viz.Staphylococcus aureus (J), Streptococcus pneumonia (K) are promising and the compounds can be treated as potential common antibacterial materials.

Multifunctional Transition Metal Complexes: Design, Synthesis, Luminescent Features, Electrical Behaviour, Nanostructure Morphology and Bioactive Properties with 1,1-Dicyanoethylene-2,2-dithiolate and p-Phenylenediamine Ligands

“…Antibacterial assay: The antibacterial efficacy of K2(i-MNT)•H2O, along with complexes 1-4, was assessed against pathogenic Gram-negative Escherichia coli, Shigella boydii and Gram-positive Staphylococcus aureus bacteria using the zone of inhibition (ZOI) method [29]. Additionally, the antibacterial activity of standard antibiotics, gentamycin and polymyxin B, specific to the bacterial strains, was tested as positive controls.…”

Coordinative Compounds Based on Unsaturated Carboxylate with Versatile Biological Applications

“…Organotin (IV) compounds receive special attention due to their antibacterial activities and their use as biocidal agents [55][56][57]. Considering these aspects, [Me 3 Sn(hmpp)] 54 (Me = methyl; Hhmpp = 3-(4-hydroxy-3-methoxyphenyl)-2-phenylpropenoic acid) was tested and presented a good and enhanced activity against P. aeruginosa (IZD 18 mm) in comparison with a ligand [58].…”

Boosted antibacterial efficacy: Di and triorganotin complexes via 2-[(2,3-dimethylphenyl)amino]benzoic acid

“…[2][3][4]. In order to determine the optimal performance based on the ligand attached to the organometallic fragment and the origin, organotin(IV) compounds, in particular those derived from carboxylate ligands, have been thoroughly studied as bactericides [5][6][7][8][9], anti-cancer [10][11][12], antifungal and anti-inflammatory [13][14][15], catalysts, wood preservatives and pesticides [16]. The biological activities of organotin (IV) compounds are affected by both the length of the alkyl chain and the chemical structure of these compounds; the longer the alkyl chain, the less toxic the compound.…”