Synthesis, Characterization and Elucidation of the Structure–Activity Relationship of Heteroatom Donor Ligands and Their Complexes Derived From Substituted Dithiocarbazate Derivatives

Four new substituted dithiocarbazate ligands [S-napthalen-2-ylmethyldithiocarbazate (SNMDTC), S-quinolin-2-ylmethyl-dithiocarbazate (SQ2MDTC), Sbenzyl- N-benzyldithiocarbazate (SBNBDTC) and S-methyl-N-benzyldithiocarbazate (SMNBDTC)], eight series of isomeric Schiff bases derived from different types of S-substituted dithiocarbazate and their metal complexes were successfully synthesized and characterized. Eighteen structures were determined using single crystal X-ray diffraction analysis. These newly synthesized compounds were systematically designed to form structurally heterogeneous compounds for QSAR study. Schiff bases were derived from condensation of isomeric aldehydes and ketones, 3- and 4-methylacetophenone and 2-, 3- and 4-acetylpyridine with different substituted dithiocarbazate compounds. Upon complexation, all Schiff bases formed bis chelated (NS donor) complexes except for the uninegative tridentate, S-napthalen- 2yl methyl-β-N-(2-acetylpyridine)dithiocarbazate (SNM2AP) that coordinated with metal ions via the azomethine nitrogen atom, the pyridyl nitrogen atom and the thiolo sulfur (NNS donor) Some of these newly synthesized compounds exhibited significant activities towards selective strains of pathogens and marked cytotoxicity when assayed against breast cancer estrogen receptor positive, MCF-7 and breast cancer estrogen receptor negative, MDA-MB-231 cell lines. The biological activities of the isomeric Schiff bases and their complexes were investigated. Most of the complexes exhibited higher activity compared to their parent ligands upon complexation with metal ions. The cytotoxicity data for all the compounds were used to construct QSAR model in an attempt to elucidate the relationship between structure and bioactivity. Satisfactory QSAR models were developed focusing on a few of the informative descriptors based on a wide set of relatively heterogeneous compounds as evidenced with value r2>0.6 and r2 CV> 0.5

Synthesis, Characterization And Biological Studies Of Substituted Thiadiazine Derivatives And Their Metal Complexes

Numerous works have been done to study and investigate thiadiazines and their substituted derivatives. The main reason that initially stirred up researchers’ interest to further pursue these compounds was due to the fact that they are biologically active. A total of twenty compounds were synthesized and characterized successfully. They comprised sixteen substituted thiadiazine derivatives and four metal complexes. The purity of the compounds were determined using thin layer chromatography because most of the compounds are sticky and semi-solid. The compounds were characterized using CHNS analyses, FAAS analyses, FTIR analyses and NMR analyses. Cytotoxic assay was done to determine the cytotoxic activities of the compounds against human colorectal adenocarcinoma cell line, HT29

Synthesis and characterization of putrescine-sulfur analogue/ Adzly H. Sahabudin, Fiona How Ni Foong and Radiah Abdul Ghani

Cancer is a disease which has high motility rate worldwide. The current treatment has a high potential to kill cancer cells, however it is lacking of specificity and therefore cause the side effects in normal cells. The alternate pathway has been explored including targeting to cancer cells via polyamine transport system (PTS). The PTS activity is highly upregulated in cancer cells compared to normal cells. In this study, one of the polyamines called putrescine was being exploited to be a vector for sulphur. This putrescinesulphur analogues were synthesized using two different methods. The synthesized product was later characterized using various physicochemical techniques such as gas-chromatography and Fourier transformed-infrared spectroscopy for structural determination. Several putrescine-sulphur analogues was succesfully synthesis with the expected structure

Synthesis, Characterization, Antimicrobial activity and ADMET Analysis of S-benzyl-α-N-(anisoyl)-dithiocarbazate and its metal complexes

Dithiocarbazate derivatives have shown significant bioactivities especially as antibacterial agents. However due to the poor penetration into bacteria and its toxicity, their potential as a good antibacterial agent was dismissed. Therefore, the purpose of this study was to synthesize a new substituted dithiocarbazate derivative, S-benzyl-α-N-(anisoyl) dithiocarbazate (SB4OME) and its metal complex. SB4OME behaves as a tridentate chelating agent that coordinates with the metal ions with the general formula of [M(SB4OME)2] where M is Cu2+, Zn2+, Co2+ and Ni2+. All the compounds were characterized with various physico-chemical techniques including melting point analysis, FT-IR spectroscopy, UV–Vis spectroscopy, NMR spectroscopy, magnetic susceptibility and molar conductivity measurements. The antibacterial activity of all the compounds was tested against Staphylococcus aureus (ATCC 25923), Bacillus cereus (ATCC 11778), Pseudomonas aeruginosa (ATCC 27853) and Escherichia coli (ATCC 25922). The complexes significantly exhibited a stronger antibacterial activity than SB4OME against specific bacteria. All compounds showed a good drug like character through ADMET investigation, which was determined using SwissADME and Pro Tox-II. This showed that SB4OME and its complexes reduced the toxicity of dithiocarbazate derivatives and significantly enhanced their penetration in bacteria due to the coordination with metal ions resulting in increased bioactivity

Crystal structure of benzyltriphenylphosphonium chloride monohydrate

The title compound, Ph3(PhCH2)P+ Cl-·H2O, was obtained unintentionally as the product of an attempted synthesis of a silver dithiocarbamate complex using benzyltriphenyl- phosphonium as the counter-ion. The asymmetric unit consists of a phosphonium cation and a chloride anion, and a water molecule of crystallization. In the crystal, the chloride ion is linked to the water molecule by an O—H·· ·Cl hydrogen bond. The three units are further linked via C—H·· ·Cl and C— H·· ·O hydrogen bonds and C—H··· JT interactions, forming a three-dimensional structure

Benzyl N0-[1-(3-pyridyl)ethylidene]-hydrazinecarbodithioate

The title compound, C15H5N2S2, crystallizes as a trans–cis conformer. The thione sulfur is in a trans position with the methyl pyridyl fragment with respect to the C—N bond but adopts a cis position with the benzyl ring across the C—S bond. The dihedral angle between the planar quinoline ring and the dithiocarbazate unit is 103.70 (1). The inclination of the dithiocarbazate unit with the benzyl group is 17.20 (1).There are strong – stacking interactions between pairs of dithiocarbazate units and also pairs of pyridine rings [3.27 (5)and 3.28 (5) A ° , respectively]. A long-distance intermolecular N—H N hydrogen bond [3.171 (2) A ° ] also stabilizes the structure

2,5-Bis(2-naphthylmethylsulfanyl)-1-thia-3,4 diazacyclopenta-2,5-diene

The title molecule, C24H18N2S3, consists of three essentially planar fragments viz. two methylnaphthalene groups and a five-membered thiadiazole ring. The dihedral angles between the two methylnaphthalene groups and the central 1-thia-3,4-diazacyclopenta-2,5-diene group are 78.9 (1) and 68.8 (1)°. In the crystal structure, - stacking interactions exist between pairs of symmetry-related naphthalene fragments with an interplanar separation of 3.35 Å. All bond lengths and angles are comparable with previous reports except that both C-S bond lengths are slightly longer than normal. In addition, the C-S-C and S-C-C bond angles appear to be smaller than normal and this could be due to the steric hindrance of the methylnaphthalene fragments

2-Quinolylmethyl N0-[1-(m-tolyl) ethylidene] hydrazinecarbodithioate

The title compound, C20H19N3S2, crystallized as a cis–trans conformer in which the quinoline ring system is cis across the C—S bond but adopts a trans geometry with respect to the C—N bond. The compound exists in the thione form with the presence of a C S bond