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

Abstract

The title compound bis[2-hydroxybenzylidenehydrazono)(methylthio)methyl]disulfide (1), an S-methyldithiocarbazate derivative with a disulfide bond has been synthesized by the condensation of 2-hydroxybenzaldehyde with S-methyldithiocarbazate. It has been characterized by elemental analyses, 1 H, 13 C NMR and FT-IR spectroscopy and mass spectrometry. The single crystal X-ray structure shows that the compound exists in a tautomeric thione form with the dithiocarbazate fragment adopting an EE configuration with respect to the C=N bond of the benzylidene moiety. The thermal behaviour of the compound has been studied using thermogravimetric analysis (TGA). The molecular geometry of the compound in the ground state has been optimized using density functional theory (DFT/B3LYP) method with the 6-311++G(d,p) basis sets. Molecular docking of the compound with human carbonic anhydrase II has been performed to probe the nature of interaction.

2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study

“…These molecules are effective ligands for a variety of metals and the motivation for complexation largely stems from the promising biological activity exhibited by the derived metal complexes (Low et al, 2016;Ravoof et al, 2017;Yusof et al, 2020). However, these Schiff bases are susceptible to oxidation resulting in the formation of a disulfide bond, as has been observed previously (Amirnasr et al, 2014;Sohtun et al, 2018). This is the case in the present report where the title compound, (I), was the side-product from the synthesis of the Schiff base, 4-methylbenzyl-2-(2-hydroxybenzylidene) hydrazinecarbodithioate (Ravoof et al, 2010).…”

Interactions between Ibuprofen and Silicified-MCC: Characterization, Drug Release and Modeling Approaches

“…Similarity or equivalence between two dissolution profiles is based on f 1 ≤ 15 and f 2 ≥ 50. [35][36][37] Significantly improved drug dissolution of solid state milling, and aqueous state kneading and freeze drying has been understood by using f 1 Crystalline ibuprofen exhibited only 52.89 % dissolution whereas, dry-state co-milling and freeze dried co-processed material has improved dissolution to a great extent (85.84 and 81.35 % respectively). Silicified microcrystalline cellulose has shown more impact in solid state milling compared to aqueous state kneading and equilibration and brought about more amorphization of ibuprofen.…”

“…Molecular docking experiment was used to predict the binding mode interactions between the molecules. 1 The program uses Lamarckian genetic algorithm, semi empirical free energy force field, grid box based method to allow rapid evaluation of the binding energy and pre-calculating the interaction between every atom type pair at every distance and result clustering procedures. The force field is based on a comprehensive thermodynamic model that allows incorporation of intramolecular energies into the predicted free energy of the binding.…”

The synthesis of N,N′-disulfanediyl-bis(N′-((E)-benzylidene)acetohydrazide) from (E)-N′-benzylideneacetohydrazide and S8

“…Many oxidants such as oxygen or air, 11,12 hydrogen peroxide, 13 halogens, 14 high-valent sulfur compounds 15 and other agents 16 were applied (Scheme 1B). In addition, methyl (E)-2-(2-hydroxybenzylidene)hydrazine-1-carbodithioate 17 and N-phenacylbenzothiazolium bromides 18 have also been used as starting materials to produce disuldes (Scheme 1C). Different from these C-S-S-C bonds, there are only a few reports in the literatures that describe N-S-S-N bond formation.…”