144977-70-8

Basic information

• Product Name: N-methyl-2-[1-(pyridin-2-yl)ethylidene]hydrazine-1-carbothioamide
• CAS NO: 144977-70-8
• Molecular Weight: 208.287
• Mol File: 144977-70-8.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: N-methyl-2-[1-(pyridin-2-yl)ethylidene]hydrazine-1-carbothioamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-2-[1-(pyridin-2-yl)ethylidene]hydrazine-1-carbothioamide(144977-70-8)
• EPA Substance Registry System: N-methyl-2-[1-(pyridin-2-yl)ethylidene]hydrazine-1-carbothioamide(144977-70-8)

Safety Data

• Hazardous Substances Data: 144977-70-8(Hazardous Substances Data)

Upstream product

• 1122-62-9 2-acetylpyridine 
• 6610-29-3 4-methylthiosemicarbazide 

Relevant articles and documents

Synthesis, characterization and crystal structure of cobalt(III) complexes containing 2-acetylpyridine thiosemicarbazones: DNA/protein interaction, radical scavenging and cytotoxic activities

The synthesis, structure and biological studies of cobalt(III) complexes supported by NNS-tridentate ligands are reported. Reactions of 2-acetylpyridine N-substituted thiosemicarbazone (HL1-3) with [CoCl 2(PPh3)2/sub

Desing and synthesis of potent anti-Trypanosoma cruzi agents new thiazoles derivatives which induce apoptotic parasite death

Chagas disease, caused by the kinetoplastid protozoan parasite Trypanosoma cruzi, remains a relevant cause of illness and premature death and it is estimated that 6 million to 7 million people are infected worldwide. Although chemotherapy options are limited presenting serious problems, such as low efficacy and high toxicity. T. cruzi is susceptible to thiazoles, making this class of compounds appealing for drug development. Previously, thiazoles resulted in an increase in anti-T. cruzi activity in comparison to thiosemicarbazones. Here, we report the structural planning, synthesis and anti-T. cruzi evaluation of new thiazoles derivatives (3a-m and 4a-m), designed from molecular hybridization associated with non-classical bioisosterism. By varying substituents attached to the phenyl and thiazole rings, substituents were observed to retain, enhance or greatly increase their anti-T. cruzi activity, in comparison to the corresponding thiosemicarbazones. In most cases, electron-withdrawing substituents, such as bromine, 3,4-dichloro and nitro groups, greatly increased antiparasitic activity. Specifically, new thiazoles were identified that inhibit the epimastigote proliferation and were toxic for trypomastigotes without affecting macrophages viability. These compounds were also evaluated against cruzain. However, inhibition of this enzyme was not observed, suggesting that the compounds work through another mechanism. In addition, examination of T. cruzi cell death showed that these molecules induce apoptosis. In conclusion, except for compounds 3h and 3k, all thiazoles derivatives evaluated exhibited higher cytotoxic activity against the trypomastigote forms than the reference medicament benznidazole, without affecting macrophages viability. Compounds 4d and 4k were highlights, CC50 = 1.2 e 1.6 μM, respectively. Mechanistically, these compounds do not inhibit the cruzain, but induce T. cruzi cell death by an apoptotic process, being considered a good starting point for the development of new anti-Chagas drug candidates.

Unusual saccharin-N,O (carbonyl) coordination in mixed-ligand copper(II) complexes: Synthesis, X-ray crystallography and biological activity

Three tridentate Schiff bases containing N and S donor atoms were synthesized via the condensation reaction between S-2-methylbenzyldithiocarbazate with 2-acetyl-4-methylpyridine (S2APH); 4-methyl-3-thiosemicarbazide with 2-acetylpyridine (MT2APH) and 4-ethyl-3-thiosemicarbazide with 2-acetylpyridine (ET2APH). Three new, binuclear and mixed-ligand copper(II) complexes with the general formula, [Cu(sac)(L)]2 (sac?=?saccharinate anion; L?=?anion of the Schiff base) were then synthesized, and subsequently characterized by IR and UV/Vis spectroscopy as well as by molar conductivity and magnetic susceptibility measurements. The Schiff bases were also spectroscopically characterized using NMR and MS to further confirm their structures. The spectroscopic data indicated that the Schiff bases behaved as a tridentate NNS donor ligands coordinating via the pyridyl-nitrogen, azomethine-nitrogen and thiolate-sulphur atoms. Magnetic data indicated a square pyramidal environment for the complexes and the conductivity values showed that the complexes were essentially non-electrolytes in DMSO. The X-ray crystallographic analysis of one complex, [Cu(sac)(S2AP)]2 showed that the Cu(II) atom was coordinated to the thiolate-S, azomethine-N and pyridyl-N donors of the S2AP Schiff base and to the saccharinate-N from one anion, as well as to the carbonyl-O atom from a symmetry related saccharinate anion yielding a centrosymmetric binuclear complex with a penta-coordinate, square pyramidal geometry. All the copper(II) saccharinate complexes were found to display strong cytotoxic activity against the MCF-7 and MDA-MB-231 human breast cancer cell lines.

Self-organized three dimensional architectures based on non-covalent interactions in square planar Cu(II) thiosemicarbazone: Solvent mediated crystallization and EPR based correlation study

A series of copper complexes of 2-acetylpyridine-N4-methylthiosemicarbazone (HL4M) were synthesized and characterized by elemental analyses, UV–Vis, FT-IR, conductivity and EPR studies. The molecular structures of [Cu(L4M)Cl] (1), [Cu(L4M)I] (2), [Cu(L4M)OAc]·H2O (3) and [Cu(μ-S-L4M)(NCS)]2·DMSO (4) were confirmed by single crystal X-ray crystallography. Complexes 1, 2 and 3 have square planar geometry constituted by NNS donor sites from deprotonated thiosemicarbazone ligand and the fourth site is occupied by anionic group/atom. Complex 4 is a centrosymmetric dimer. The XRD results revealed that the solvents play a decisive role in the crystallization of products. These four complexes exhibit strong hydrogen bonding interactions in the solid state and are self-assembled into infinite 3D supramolecular structure via π?π stacking interactions. The g|| and A|| of complexes were analyzed by Peisach–Blumberg plot which proves an inverse correlation among NNS and ONS thiosemicarbazone complexes.

A thiosemicarbazone copper(II) complex as a potential anticancer agent

The preparation and the structure of a copper(II) complex, [Cu(4ML)Cl] (1) (H4ML = 2-acetylpyridine-4-methylthiosemicarbazone), are described. Complex 1 crystallizes in a monoclinic P21/c space group with a = 7.977(2) ?, b = 15.824(5) ?, c = 9.126(2) ?, α = γ = 90°, β = 91.974(2)°, V = 1151.26(5) ?3, Z = 4, F(0 0 0) = 620. According to X-ray crystallographic studies, each Cu(II) ion lies in a square planar coordination geometry based on the 4ML- and Cl- ligands. The complex displayed excellent inhibitory activity against various tumor cells (HeLa, HepG-2 and SGC-7901), offering lower IC50 value of 3.2 ± 0.7 M than cisplatin (10 ± 2 M) on HeLa cells at 48 h. Complex 1 could significantly suppress HeLa cell viability in a dose-dependent manner. Flow cytometric analysis showed that 1 induced HeLa cell apoptosis, which might be associated with cell cycle arrests at S and G2 phases. Consistent with results of DNA cleavage experiments, comet assay indicated that 1 caused severe DNA fragmentation. The production of ROS was elevated with increasing concentration of 1, suggesting that 1 was capable of promoting HeLa cell apoptosis through an oxidative DNA damage pathway.

Synthesis, antiproliferative activity and mechanism of copper(II)-thiosemicarbazone complexes as potential anticancer and antimicrobial agents

Malignant tumors have become one of the challenges to global human health today, and the development of new drugs has become a research hotspot for tumor treatment. In order to prove that copper(II)-thiosemicarbazone complexes can be used as antibacterial and antitumor agents, we have synthesized and characterized three copper(II) complexes (C1-C3). These Cu(II) complexes exhibited excellent anticancer and antimicrobial activity, and greatly exceed the corresponding metal-free ligands. C3 has the highest anti-proliferative activity (0.20 ± 0.04 μM) against A549 (human lung carcinoma cell lines) and the best inhibitory zone diameter (25.78 ± 0.18 mm) against E. coli. The lipophilicity of the ligand is closely related to the anti-proliferative and antibacterial activities of these Cu(II) complexes. The study of the cellular mechanism demonstrates that these Cu(II) complexes promoted cell apoptosis by catalyzing hydrogen peroxide to produce intracellular reactive oxygen species (ROS). Antibacterial experiments showed that these Cu(II) complexes exhibited potent antibacterial activities, especially against gram-negative bacteria. These Cu(II) complexes may initially cause outer membrane/lipopolysaccharide (LPS) instability, disrupt cell membranes, and ultimately lead to bacterial cell lysis.

Tin complex with 2-acetyl pyridine thiosemicarbazone as ligand and synthesis method thereof

The invention discloses a tin complex taking 2-acetyl pyridine thiosemicarbazone as a ligand and a synthesis method thereof. The synthesis method comprises the following steps of: dissolving thiosemicarbazone in methanol, adding 2-acetyl pyridine dropwise

Rhodium complexes taking 2-acetylpyridine thiosemicarbazone as ligand and synthesis method thereof

The invention discloses rhodium complexes taking 2-acetylpyridine thiosemicarbazone as a ligand and a synthesis method thereof. The three kinds of new rhodium complexes are obtained by coordination ofnitrogen heterocyclic ring-containing 2-acetylpyridine thiosemicarbazone and metal rhodium. According to the invention, in-vitro proliferation inhibition activity experiments are further carried outon the synthesized rhodium complexes, and results show that the synthesized rhodium complexes have generally better in-vitro activity than ligands thereof, show very good inhibition activity, have little toxic effect on human normal cells, and are suitable for preparation of high-efficiency and low-toxicity anti-tumor drugs.