Synthesis, spectral analysis and in vitro cytotoxicity of diorganotin (IV) complexes derived from indole‐3‐butyric hydrazide

Abstract

A series (1–20) of diorganotin (IV) complexes with general formula R2SnL were formed by the reaction of R2SnCl2 (where R = Me, Et, Bu and Ph) with Schiff base ligands (H2L1–4) derived from the reaction of indole‐3‐butyric hydrazide with the salicylaldehyde and its derivatives. The structure elucidation of compounds were done by using UV–Vis, FT‐IR, NMR (1H, 13C, 119Sn), Mass spectrometry and thermal gravimetric analysis. Spectroscopic evidences suggested tridentate nature (ONO) of Schiff base ligands and coordinated to the dialkyl/diaryltin (IV) moieties through nitrogen and oxygen donor sites giving pentacoordinated geometry to complexes. The compounds were tested for the antimicrobial activity against bacterial and fungal strains which showed promising biological activity with compound 20 (Ph2SnL4) as most active against microbes. The in silico study of the compounds was carried and observed that the compounds are used as orally active drugs and promote the formation of different hydrazide based drugs. The synthesized compounds were tested against human carcinoma cell lines namely A549, MCF7 and one normal cell line IMR 90 using MTT assay. The diethyl and dibutyltin complexes of Schiff bases displayed good cytotoxic activities. Compound 3 (H2L3) and 10 (Et2SnL2) were most potent against cancer cell lines with lowest IC50 values and 7–8 times less toxic against the normal cell line.

Synthesis, characterization, antifungal and antibacterial activities evaluation of copper (II), zinc (II) and cadmium (II) chloride and bromide complexes with new (E)‐1‐(3,4‐dimethoxybenzylidene)‐4‐methylthiosemicarbazone ligand

“…Also, the spectrum of the zinc complex showed two vibrations bands, ν (M–S) at 330 cm −1 and ν (M–Br) at 270 cm −1 , which corresponded to coordination bonds. [ 4,17,34 ] The same differences were observed when passing from the ligand ( L ) to [CdCl 2 (MTSVT) 2 ] ( 3 ) and [CdBr 2 (MTSVT) 2 . H 2 O] ( 4 ).…”

“…[ 34–36 ] However, the N1–N2 [1.380(18) Å] and N2–C2 [1,348(2) Å] bond distances observed are intermediate between the ideal values of the corresponding single [N–N, 1.45 Å; C–N, 1.47 Å] and double bonds [N=N, 1.25 Å; C=N 1.28 Å], which are in support of an extended π delocalization along the thiosemicarbazone chain. [ 4,35 ] The sulfur atom S1 and the nitrogen atom of the imine N3 are in trans position relative to the C1–N2 bond. This configuration is stabilized by the presence of an intermolecular hydrogen bond (Figure S1 and Table S2).…”

“…Thiosemicarbazone (TSC) derivatives can adopt various coordination modes as N , S ‐donors, and their transition metal complexes have been studied because of their biological [ 1–3 ] and pharmaceutical [ 4,5 ] activities. TSCs and their metal complexes have been demonstrated to exhibit high biological activity against malarial, [ 6–8 ] bacterial [ 9 ] and fungal infections, [ 9,10 ] and displayed promising antitumor activity against various cancer cell lines.…”

A Six‐Armed Phenhomazine Ligand with a Potential “Turn‐Off” Copper(II) Sensing Capability through Terbium(III) Luminescence Quenching

“…To get a deeper insight concerning the coordination mode of Cu II with 1 , a new titration was performed by using 1 H NMR spectroscopy. Owing to the paramagnetic nature of Cu II , the diamagnetic ion Zn II was used as a model, as several reports show that the coordination mode and stoichiometry should not vary substantially between these two ions …”

Cellular Basis of Organotin(IV) Derivatives as Anticancer Metallodrugs: A Review

“…Devi et al (2020) reported a series of diorganotin(IV) compounds derived from the reaction of indole-3-butyric hydrazide with salicylaldehyde and its derivatives (Scheme 1). The hydrazone Schiff base ligands were as follows:Nʹ-(2-hydroxybenzylidene)-4-(1H-indole-3-yl) butanehydrazide [H 2 L 1 ], Nʹ-(2-hydroxy-5 nitrobenzylidene)-4-(1H-indole-3-yl)butanehydrazide [H 2 L 2 ], Nʹ-(5-diethylamino)-2 hydroxybenzylidene-4-(1H-indole-3-yl) butanehydrazide [H 2 L 3 ], and Nʹ-(3,5-dibromo-2 hydroxybenzylidene)-4-(1Hindole-3-yl)butanehydrazide [H 2 L4 ].…”