Synthesis, characterization, and antibacterial activity of organotin(IV) complexes with 2-hydroxyacetophenone thiocarbohydrazone

Chee, Dayang Norafizan Awang; Affan, Md. Abu; Ahmad, Fasihuddin B.; Asaruddin, Mohd Razip; Sam, Norrihan B.; Salam, Md. Abdus; Ismail, A Manal; Tan, Siew‐Ann

doi:10.1080/00958972.2011.631532

Cited by 29 publications

(10 citation statements)

References 18 publications

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“…The significant antimicrobial activity of (I) may be ascribed to its low molecular mass, low internal energy (high stability), low dipole moment and low HOMO value facilitating efficient diffusion across the cell membrane in consonance with previous reports …”

Section: Decomposition Kineticssupporting

confidence: 90%

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

Choudhary

Bhatt

Dash

et al. 2020

Applied Organom Chemis

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The new diorganotin (IV) complexes of composition [Me2SnCl(3,5‐(NO2)2C6H2(OH)CONHO)] (I) and [n‐Bu2SnCl(3,5‐(NO2)2C6H2(OH)CONHO)] (II) have been synthesized by the reactions of Me2SnCl2 and n‐Bu2SnCl2 with potassium 3,5‐dinitrosalicylhydroxamate [3,5‐(NO2)2C6H2(OH)CONHOK]‐ a ligand of biological significance bearing –NO2 and –OH substituents presumed to yield complexes with efficient bioactivity. The complexes have been characterized by elemental analyses, IR, 1H, 13C and 119Sn NMR and mass spectrometry in order to study the ligational behavior and probale geometry around tin as the ligand might show different bonding modes and geometry in complexes. The geometries of (I) and (II) have been computed using B3LYP/6–31 + G(d,p) set by DFT method and the vibrational frequencies, 1H and 13C NMR spectra compared with the experimental data. A comparison of computed bond lengths (C=O, C‐N, and N‐O) of (I) and (II) with that of free ligand, the Sn‐O bond lengths, bond angles coupled with 119Sn NMR and IR spectral data have suggested coordination through carbonyl and hydroxamic oxygens (O, O coordination) displaying five‐coordinate distorted trigonal‐bipyramidal geometry around tin. The thermal behavior of (I) and (II) has been studied by thermogravimetric techniques (TGA, DTG, DTA) and various kinetic parameters have been calculated. The electrochemical behavior of ligand, (I) and (II) studied by cyclic voltammetric technique has shown ligand centered redection. The HOMO‐LUMO energies and orbitals, global reactivity descriptors, various thermodynamic parameters and dipole moment (μ) have been computed to determin the molecular properties of complexes. The in vitro antimicrobial activity assay against bacteria and fungi by MIC method has indicated higher potency of (I) than (II). The in vitro cytotoxicity on human muscle rhabdomyosarcoma (RD) by MTT method and the antioxidant potential by DPPH free radical scavenging showed higher inhibitory effect of complexes than ligand.

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Section: Decomposition Kineticssupporting

confidence: 90%

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

Choudhary

Bhatt

Dash

et al. 2020

Applied Organom Chemis

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“…Few works have been reported on organotin(IV) complexes with thiocarbohydrazone, for this reason, the work of Chee et al is noteworthy, focusing on six new complexes obtained by direct reaction of RSnCl 3 (R = Me, Bu and Ph) or R 2 SnCl 2 (R = Me, Bu and Ph) and 2-hydroxyacetophenone thiocarbohydrazone (3a, Scheme 3) [37]. They were screened for antibacterial activity against Escherichia coli, Staphylococcus aureus, Salmonella typhi and Enterococci aeruginosa.…”

Section: Symmetric Thiocarbohydrazones Derived From Salycilaldehyde Amentioning

confidence: 99%

Biological Applications of Thiocarbohydrazones and Their Metal Complexes: A Perspective Review

2019

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Although organic compounds account for more than 99% of currently approved clinical drugs, the established clinical use of cisplatin in cancer or auranofin in rheumatoid arthritis have paved the way to several research initiatives to identify metal-based drugs for a wide range of human diseases. Nitrogen and sulfur donor ligands, characterized by different binding motifs, have been the subject in recent years of one of the main research areas in coordination chemistry. Among the nitrogen/sulfur compounds, very little is known about thiocarbohydrazones (TCH), the higher homologues of the well-known thiosemicarbazones (TSC), and their metal complexes. The extra hydrazine moiety provides the ligands of variable metal binding modes, structural diversity and promising biological implications. The interesting coordination chemistry of TCH has mainly been focused on symmetric derivatives, which are relatively simple to synthesize while few examples of asymmetric ligands have been reported. This informative review on TCHs and their metal complexes will be helpful for improving the design of metal-based pharmaceuticals for applications ranging from anticancer to antinfective therapy.

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“…The ligands thus obtained were designated as SM, SIP, PM, and PIP, respectively. (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) were prepared by treating 2 mol of half-esters (ligands) with 1 mol of dialkyltin dichloride using Scheme 2.…”

Section: Synthesismentioning

confidence: 99%

“…Tributyl and triphenyltin chlorides find extensive use as biocidal additives in marine antifouling paints [6]. Synthesis and structural studies of neutral tin complexes derived from ligands with strategically placed donors (O, N, and S) have received attention [7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Diorganotin complexes of carboxylates: synthesis and characterization

Chilwal

Deep

Malhotra

et al. 2013

Journal of Coordination Chemistry

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Diorganotin complexes of monoisopropyl and monomethyl nadiate, succinate, and phthalate were synthesized and characterized by elemental analysis, FT-IR, 1 H NMR, 13 C NMR, and 119 Sn NMR spectroscopic techniques. The spectroscopic investigation demonstrated that carboxylate is bidentate in the diorganotin complexes. On the basis of 1 J( 119 Sn-13 C) and 2 J( 119 Sn-1 H) values, C-Sn-C bond angles were also calculated. The newly synthesized complexes were also screened for their antibacterial activities against Gram-positive and Gram-negative pathogenic strains of bacteria.

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Synthesis, characterization, and antibacterial activity of organotin(IV) complexes with 2-hydroxyacetophenone thiocarbohydrazone

Cited by 29 publications

References 18 publications

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

Biological Applications of Thiocarbohydrazones and Their Metal Complexes: A Perspective Review

Diorganotin complexes of carboxylates: synthesis and characterization

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