Synthesis, characterisation and biological activity of diorganotin compounds of (E)-N'-(5-nitro-2-hydroxybenzylidene)-3-hydroxy-2-naphthohydrazide

Lee, See Mun and Lo, Kong Mun and Liew, Li Yuan and Chew, Jactty and Tan, Chun Hoe and Sim, Kae Shin and Tiekink, Edward R. T. (2022) Synthesis, characterisation and biological activity of diorganotin compounds of (E)-N'-(5-nitro-2-hydroxybenzylidene)-3-hydroxy-2-naphthohydrazide. Polyhedron, 223. ISSN 0277-5387, DOI https://doi.org/10.1016/j.poly.2022.115955.

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Abstract

Diorganotin(IV) compounds with the general formula R2SnL H2L = (E)-N'-1-(5-nitro-2-hydroxybenzylidene]-3-hydroxy-2-naphthohydrazide; R = Me (1.toluene and 1), n-Bu (2), Ph (3), Cy (4), Bz (5), o-ClBz (6) and p-ClBz (7)] have been synthesised and characterised by elemental analyses, IR, H-1, C-13{1H} and 119Sn NMR spectros-copy, thermal analysis and in the cases of 1 and 3, single crystal X-ray diffraction. Crystallography, in accord with NMR, indicate highly distorted penta-coordinate geometries whereby each C2NO2 donor set is defined by the NO2 donor atoms derived from di-anionic L and two tin-bound organo substituents. The Schiff base ligand and the corresponding diorganotin compounds have been evaluated against two colon human carcinoma cell lines (HT-29 and HCT 116) and a normal colon fibroblast cell line (CCD-18Co). Among the evaluated compounds, the n-butyl derivative, 2, is most potent and least toxic to the cancer and normal cell lines, respectively, yielding the highest safety profile (high SI). In addition, the anti-bacterial activities have been evaluated against a panel of 21 Gram positive and Gram negative bacteria. Based on the broth dilution method, non-toxic 3, exhibited promising anti-bacterial effects against two Gram positive bacteria, namely, Enterococcus faecalis and Staphylo-coccus epidermidis.

Item Type: Article
Funders: Sunway University Sdn Bhd (Grant No: GRTIN-IRG-01-2021 & GRTIN-IRG-08-2021), Universiti Malaya (Grant No: RP017B-14AFR), Ministry of Higher Education of Malaysia (MOHE) Fundamental Research Grant Scheme (FRGS) (Grant No: FP033-2014B)
Uncontrolled Keywords: Diorganotin; Penta-coordination; X-ray structure; Cytotoxic activity; Anti-bacterial activity
Subjects: Q Science > QD Chemistry
Q Science > QH Natural history > QH301 Biology
Divisions: Faculty of Science > Institute of Biological Sciences
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 03 Nov 2023 09:25
Last Modified: 03 Nov 2023 09:25
URI: http://eprints.um.edu.my/id/eprint/41529

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