Synthesis, Characterisation and Biological Activities of 2-Methylbenzyl 2-(dipyridin-2-yl methylene)hydrazinecarbodithioate

Abstract

Mixed-ligand complexes of general formula, [Cu(NNS)(sac)] (NNS′ = S-benzyl-β-N-(2acetylpyrid-2-yl)methylenedithiocarbazate, NNS″ = S-benzyl-β-N-(2-benzoylpyrid-2yl)methylenedithiocarbazate and NNS = S-benzyl-β-N-(6-methylpyrid-2-yl)methylenedithiocarbazate, sac = the saccharinate anion) have been synthesized by reacting [Cu(sac)2(H2O)4] • 2H2O with the appropriate ligands in ethanol and characterized by various physico-chemical techniques. Magnetic and spectral evidence indicate that the complexes are four-coordinate in which the Schiff bases coordinate as NNS ligands and the sac-anion coordinates as a unidentate N-donor ligand. An X-ray crystallographic structural analysis of [Cu(NNS′)(sac)] shows that the complex has a distorted square-planar geometry with the Schiff base coordinated to the copper (II) ion as a uninegatively charged tridentate chelating agent via the pyridine nitrogen atom, the azomethine nitrogen atom and the thiolate sulphur atom while the fourth coordination position is occupied by the N-bonded saccharinate anion. The complexes have been evaluated for their biological activities against selected pathogens and cancer cell lines. They display weak activity against the pathogenic bacteria and fungi. The complexes were highly active against the leukemic cell line (HL-60) but only [Cu(NNS′)(sac)] was found to exhibit strong cytotoxicity against the ovarian cancer cell line (Caov-3). All complexes were inactive against the breast cancer cell line (MCF-7).

Synthesis, Characterization, Crystal Structure and Molecular Docking Studies of a S-methyldithiocarbazate Derivative: Bis[2-hydroxy- benzylidenehydrazono) (methylthio)methyl]disulfide

“…S-methyldithiocarbazate was prepared according to the published procedure. 25 1 H and 13 C NMR spectra were recorded on a Bruker AVANCE II 400 MHz NMR spectrometer. IR spectra were recorded using Perkin-Elmer 983 model FT-IR spectrophotometer with compounds being dispersed as KBr discs.…”

Synthesis, characterisation and structure determination of 3-[(1Z)-{2-[bis({[(2-methylphenyl)methyl]sulfanyl})methylidene]hydrazin-1-ylidene}methyl]benzene-1,2-diol

“…Since the 1980's, many Schiff bases derived from dithiocarbazates have been synthesised, characterised and investigated especially for their pharmaceutical potential [1]. The variety of coordination modes in dithiocarbazates and the ease of modification by introducing different organic substituents to the dithiocarbazate derivatives [2][3][4][5][6][7] have been of interest as relatively small modifications in the structural backbone often gives rise to major differences in their biological properties. For example, many of these compounds display selective in vitro biological activity against several cancer cell lines [4,5,[7][8][9][10][11].…”

“…The variety of coordination modes in dithiocarbazates and the ease of modification by introducing different organic substituents to the dithiocarbazate derivatives [2][3][4][5][6][7] have been of interest as relatively small modifications in the structural backbone often gives rise to major differences in their biological properties. For example, many of these compounds display selective in vitro biological activity against several cancer cell lines [4,5,[7][8][9][10][11]. In addition, some dithiocarbazate ligands and their metal complexes have also investigated for other applications including as nonlinear optical (NLO) materials with diverse magnetic and electrochemical properties [12][13][14].…”

“…The single-crystal X-ray diffraction analysis of S-benzyldithiocarbazate (SBDTC) was reported thirty years after its synthetic procedure was first established [15] and since then much work has been carried out on the synthesis of analogous S-substituted dithiocarbazates: S-allyl [16], isomeric S-2-/3-/4-picolyl [17,18], isomeric S-2-/3-/4-methylbenzyl [7,19,20], Snapthylmethyl [21], S-quinolin-2yl-methyl [21], S-4-nitrobenzyl [5] and S-4-chlorobenzyl [22] dithiocarbazates and their transition metal complexes.…”

“…As part of our on-going study on Schiff bases derived from S-2-methylbenzyldithiocarbazate (S2MBDTC) [7] and 2,3-dihydroxybenzaldehyde, we report herein the unexpected formation of a compound that crystallised during the routine synthetic procedure of S-2-methylbenzylβ-N-(2,3-dihydroxybenzylmethylene)dithiocarbazate. The product, 3-[(1Z)-{2-[bis({[(2methylphenyl)methyl]sulfanyl})methylidene]hydrazin-1-ylidene}methyl]benzene-1,2-diol (1), formed from the filtrate after it was left standing for one week, which was fully characterised by X-ray crystallography, NMR, FT-IR and UV/Vis spectroscopy.…”