133978-91-3

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 5397-03-5 hydrazinecarbodithioic acid methyl ester 

Downstream Products

• 89806-12-2 2-methylsulfonyl-5-(2-oxido-2-pyridyl)-1,3,4-thiadiazole 

Relevant academic research and scientific papers

Methyl-2-arylidene hydrazinecarbodithioates: Synthesis and biological activity

Methyl-2-arylidene hydrazine-carbodithioate has not been of particular interest to researchers even though its metal complexes are extensively reported on due to their biological activity. This study examined the cytostatic and antiviral activity of twelve methyl-2-arylidene hydrazinecarbodithioates reported by many researchers as intermediates for the synthesis of thiosemicarbazides and the preparation of their metal complexes. Compounds IIc, IIi, and IIl with tridentate ligand features were found to have the lowest IC50 value (6.5 μM, ≈ 1 μM, and 0.8 μM, respectively) against HL60 human promyelocytic leukemia cells. They were also most inhibitory to human embryonic lung (HEL) fibroblast proliferation (5.3 μM, 17 μM, and 2.6 μM). Compound IIc and IIl show antiviral activity against wild-type herpes simplex virus (HSV), varicella zoster virus (VZV), and acyclovirresistant HSV; however, these activities were observed at concentrations at which the compounds also markedly inhibit HL60 and HEL cell proliferation.

Heterocyclic dithiocarbazate iron chelators: Fe coordination chemistry and biological activity

The iron coordination and biological chemistry of a series of heterocyclic dithiocarbazate Schiff base ligands is reported with regard to their activity as Fe chelators for the treatment of Fe overload and also cancer. The ligands are analogous to tridentate heterocyclic hydrazone and thiosemicarbazone chelators we have studied previously which bear NNO and NNS donor sets. The dithiocarbazate Schiff base ligands in this work also are NNS chelators and form stable low spin ferric and ferrous complexes and both have been isolated. In addition an unusual hydroxylated ligand derivative has been identified via an Fe-induced oxidation reaction. X-ray crystallographic and spectroscopic characterisation of these complexes has been carried out and also the electrochemical properties have been investigated. All Fe complexes exhibit totally reversible FeIII/II couples in mixed aqueous solvents at potentials higher than found in analogous thiosemicarbazone Fe complexes. The ability of the dithiocarbazate Schiff base ligands to mobilise Fe from cells and also to prevent Fe uptake from transferrin was examined and all ligands were effective in chelating intracellular Fe relative to known controls such as the clinically important Fe chelator desferrioxamine. The Schiff base ligands derived from 2-pyridinecarbaldehyde were non-toxic to SK-N-MC neuroepithelioma (cancer) cells but those derived from the ketones 2-acetylpyridine and di-2-pyridyl ketone exhibited significant antiproliferative activity.

TUMOUR TREATMENT AGENTS AND METHOD

N1-(3-Methoxypropyl)-2-(pyridylmethylidene)-hydrazine-1-carbothioamide (I) and its Cu2+, Pd2+ and Pt2+ complexes are effective anti-tumor agents. Also disclosed are compositions comprising (I) and its Cu2+, Pd2+ and Pt2+ complexes, and the use of the compositions in the treatment of malignant tumors.

New 2-pyridinealdehyde N4-hydroxyethyl thiosemicarbazone and their Cd(II) and Cu(II) complexes: Synthesis, spectral, in vitro antibacterial activity and molecular and supramolecular structure study

N4-hydroxyethyl-pyridinealdehyde thiosemicarbazone (HL, 1) as a tridentate Schiff base has been synthesized by 1:1 reaction of S-methyl-3-((pyridyl)methyl) dithiocarbazate and 2-aminoethanol. Complexes [Cd(HL)2](NO3)2 (2), [Cd(HL)I2] (3), [Cd(HL)Cl2] (4), [Cu(HL)2](NO3)2 (5) and [Cu(HL)Cl2] (6) have been obtained and characterized by elemental analyses, molar conductivities, and spectroscopic studies. The ligand molecule binds the metal ion using pyridyl nitrogen, azomethine nitrogen and the sulfur atoms. The crystal structure analysis of 3 has been determined and showed to be a distorted square pyramidal geometry complex. The inter- and intramolecular interactions give rise to a supramolecular network. Compounds 2, 3, 5 and 6 were assayed for their bioactivities against selected pathogens. Copper(II) complexes 5 and 6 showed antimicrobial activities against Gram-positive (Bacillus anthracis) and Gram-negative (Pseudomonas aeruginosa and Yersinia pseudotuberculosis) bacteria, complexes 2-4 showed antimicrobial activities against Bacillus atrophaeus, while the ligand itself showed antimicrobial activities against Escherichia coli and Y. pseudotuberculosis.

Ruthenium(II) hydrido complexes of S-methyldithiocarbazates

Reactions of [RuHCl(CO)(PPh3)3] and [RuH2(CO)(PPh3)3] with schiff bases (HL) derived from S-methyldithiocarbazate and pyridine-2-aldehyde, 2-acetylpyridine, thiophene-2-aldehyde, 2- acetylthiophene and furan-2-aldehyde lead to the formation of neutral complexes of the type [RuX(CO)(PPh3)2L] (X = H or Cl). The probable stereochemistries of the complexes have been established on the basis of elemental analysis, IR, 1H and 13C NMR studies. The triphenylphosphines are trans leaving CO and H or Cl cis to each other in the complexes.

NMR-Spectroscopic Investigation of E/Z-Isomerism in Substituted Dithiocarbacinic Acid Derivatives

NMR-spectroscopic investigations of substituted dithiocarbacinic acid derivatives show the existence of configurational isomers relative to the C=N double bond, but no tautomerism.We applied chemical shift differences in the 1H-, 13C- and 15N-NMR-spectra, N-H and C-H coupling constants and NOE difference measurements in the solvents CDCl3, DMSO-d6 and partly CD3OD in order to discriminate between the isomers and to determine the configurational composition.Compounds 4 and 5 exist as E-isomers in all solvents, compounds 1, 2 and 3 as a mixture of E/Z-isomers.In DMSO-d6 the E-form is the preferred isomer.