142564-62-3

Basic information

• Product Name: (E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide
• Synonyms: (E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide
• CAS NO: 142564-62-3
• Molecular Formula: C₈H₁₀N₄S
• Molecular Weight: 194.26
• Mol File: 142564-62-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 349°Cat760mmHg
• Flash Point: 164.8°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 4.86E-05mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: (E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide(142564-62-3)
• EPA Substance Registry System: (E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide(142564-62-3)

Safety Data

• Hazardous Substances Data: 142564-62-3(Hazardous Substances Data)

Usage

Description

(E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide, commonly referred to as a thiosemicarbazone, is a chemical compound with the molecular formula C8H10N4S. It belongs to the hydrazine derivative family and is recognized for its potent inhibition of the enzyme dihydrofolate reductase, which is essential in folate metabolism. Thiosemicarbazones, including this compound, have been the subject of extensive research due to their potential antitumor, antiviral, antimicrobial, and antiparasitic activities. Their diverse pharmacological applications and ongoing research in medicinal chemistry make them a promising class of compounds for various therapeutic purposes.

Uses

Used in Pharmaceutical Industry:
(E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide is used as an active pharmaceutical ingredient for its potential antitumor properties. As a potent inhibitor of dihydrofolate reductase, it disrupts folate metabolism, which is vital for the synthesis of DNA and RNA, thereby inhibiting the proliferation of cancer cells.
Used in Antiviral Applications:
In the field of antiviral research, (E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide is utilized for its potential to combat viral infections. Its antiviral activity is attributed to its ability to interfere with essential metabolic pathways in viruses, thus limiting their replication and spread within the host.
Used in Antimicrobial Applications:
Within the antimicrobial sector, (E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide is employed as a compound with potential to inhibit the growth of various microorganisms, including bacteria and fungi. Its antimicrobial properties make it a candidate for the development of new antibiotics and antifungal agents to address the growing issue of drug-resistant infections.
Used in Antiparasitic Applications:
In the antiparasitic industry, (E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide is used for its potential to treat parasitic infections. Its antiparasitic activity is valuable in the development of new therapeutics against various parasites that cause diseases in humans and animals.
Overall, (E)-2-(1-(2-Pyridinyl)ethylidene)hydrazinecarbothioamide, as a thiosemicarbazone, holds significant promise in multiple areas of the pharmaceutical and medical fields due to its diverse biological activities and potential applications in treating various diseases and infections.

InChI:InChI=1/C8H10N4S/c1-6(11-12-8(9)13)7-4-2-3-5-10-7/h2-5H,1H3,(H3,9,12,13)/b11-6+

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 67-56-1 methanol 
• 79-19-6 thiosemicarbazide 
• 1122-62-9 2-acetylpyridine 

Downstream Products

• 1599467-47-6 C₁₇H₁₃N₅S 

Relevant articles and documents

2-Acetylpyridine thiosemicarbazones are potent iron chelators and antiproliferative agents: Redox activity, iron complexation and characterization of their antitumor activity

Through systematic structure-activity studies of the 2-benzoylpyridine thiosemicarbazone (HBpT), 2-(3- nitrobenzoyl)pyridine thiosemicarbazone (HNBpT) and dipyridylketone thiosemicarbazone (HDpT) series of iron (Fe) chelators, we identified structural fea

Synthesis and characterisation of new homoleptic rhenium thiosemicarbazone complexes

A series of new rhenium(III) complexes, [ReL2]+, where LH = a 2-formylpyridine thiosemicarbazone have been synthesised and characterised. The complexes have been synthesised from the Re(v) starting material [ReOCl3(PPh3)2] and from [ReO4]- in the presence of triphenylphosphine. All of the new compounds have been characterised by X-ray crystallography, NMR and mass spectroscopy. In all cases the Re atom is in a distorted octahedral environment with two tridentate deprotonated thiosemicarbazones binding as monoanionic ligands through the sulfur, pyridyl nitrogen and azamethinic nitrogen in a mer (azomethine nitrogen atoms trans) configuration. Electrochemical measurements show that the complexes undergo two reversible reductions at biologically accessible potentials. Under certain conditions the 2-formylpyridine thiosemicarbazone ligands undergo reductive cleavage of the hydrazinic N-N bond resulting in the formation of a rhenium complex of methyl(2-pyridyl)methyleneimine which has been characterised by X-ray crystallography.

Gold complexes with thiosemicarbazones: Reactions of bi- And tridentate thiosemicarbazones with dichloro2-(dimethylaminomethylphenyl-CilgoldCm), [Au(damp-C1A)Cl2]

Dichloro[2-(A,A-dimethylaminomethyl)phenyl-C1,A]gold(iii), [Au(damp-C,A)Cl2] (1), reacts with salicylaldchyde thiosemicarbazone (H2saltsc), vanilline thiosemicarbaezone (Hvantsc), N-methylpyrrole aldehyde thiosemicarbazone (Hmepyrtsc), pyridoxal methylthiosemicarbazone (H2pydoxmetsc), 2-diphenylphosphinobenzaldehyde thiosemicarbazone (HPtsc) or variously substituted acetylpyridine thiosemicarbazones (HapRtsc; R = H, Me, Ph) with cleavage of the Au-N bond and protonation of the dimethylamino group. Compounds of general formulae [Au(Hdamp-C1)CI(L)f (L = Hsaltsc-, vantsc-, mepyrtsc1), [Au(Hdamp-C1)Cl(L)]2+ (L = H2pydoxmetsc) or [Au(Hdamp-C1)(L)]2+ (L = Ptsc-, apRtsc-, R = H, Me, Ph) have been isolated and characterized. The presence of the (T-bonded 2-(dimethylaminomethyl)phenyl ligand is mandatory to prevent reduction of the gold(in) centre. The crystal structures of [Au(Hdanip-C1)CI(HsaItsc)](PF6) (3a), [Au(Hdamp-C')Cl(mepyrtsc)]Cl (3c), [Au(Hdamp-C1)-CI(H2pydo.xtnetsc)]Cl2-MeOH (4), [Au(Hdamp-C1)(apPhtsc)]Cl2-2 MeOH (5c) and [Au(Hdamp-C')(Ptsc)]Cl2-1.5MeOH (6) have been elucidated, showing the gold atoms in distorted square-planar co-ordination environments. The potentially O,N,S-tridentate ligands H2saltsc and H2pydoxmetsc co-ordinate in a bidentate fashion and do not incorporate the OH groups in the chelating framework, whereas HapRtsc or HPtsc co-ordinate in a tridentate manner. Generally, one or more hydrogen atoms of the heterocyclic ligands and/or the NMe2H+ group form hydrogen bridges in the solid state structures. The preliminary results of antiproliferation tests on tumor cells demonstrate the considerable cytotoxicity of these new gold complexes. The Royal Society of Chemistry 2000.

Three Pt(II) complexes based on thiosemicarbazone: Synthesis, HSA interaction, cytotoxicity, apoptosis and cell cycle arrest

Three thiosemicarbazone-based platinum(II) complexes [Pt(MH-TSC)Cl] (1), [Pt(ME-TSC)Cl] (2) and [Pt(NH-TSC)2]Cl (3) (MH-TSC = (E)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide, ME-TSC = (E)-N-ethyl-2-(1-(pyridin-2-yl)ethylidene) hydrazinecarbothioamide, NH-TSC = (Z)-2-(amino(pyridin-2-yl)methylene)hydrazinecarbothioamide) were synthesized and structurally characterized. X-ray analyses revealed that 1 and 2 possessed similar a neutral mononuclear unit in which one tridentate TSC ligand and one leaving group (Cl-) coordinated to Pt(II) ion, while 3 was cationic and formed by two NH-TSC ligands surrounding one Pt atom in a meridional arrangement. UV-visible and fluorescence spectra of human serum albumin (HSA) with the complexes displayed that the quenching mechanism of HSA by 1-3 might be a static binding mode. Moreover, synchronous fluorescence experiments proved that 1-3 affected the microenvironment of tryptophan residues of HSA. In addition, the antiproliferative activities against MCF-7 (human breast cancer lines), HepG-2 (human liver hepatocellular carcinoma cell line), NCI-H460 (non-small cell lung cancer lines) and HeLa (human epithelial cervical cancer cell line) were screened for 1-3. Inspiringly, their cytotoxic activity (IC50 = 1.7-9.6 μM) appeared much better than that of cisplatin (IC50 = 5.2-13.5 μM) against different cell lines, respectively. Among them, complex 3 exhibited the strongest inhibition on the viability of all tested cell lines with IC50 values of 1.7-2.2 μM. Inductively-coupled plasma mass spectrometry (ICP-MS) showed that 3 accumulated rapidly in cells and reached intracellular levels of up to 10-fold higher than those determined for 1 and 2. Furthermore, fluorescence microscopic observation and flow cytometric analysis revealed that 1-3 could effectively induce apoptosis of HeLa cells, which were arrested in the S phase after treatment with 1 (30.31%) and 3 (46.96%), and in G2 phase with 2 (20.2%). All the results mentioned above suggest that complexes 1-3 might be efficient antitumor agents.

4-(3-Nitrophenyl)thiazol-2-ylhydrazone derivatives as antioxidants and selective hMAO-B inhibitors: synthesis, biological activity and computational analysis

A new series of 4-(3-nitrophenyl)thiazol-2-ylhydrazone derivatives were designed, synthesised, and evaluated to assess their inhibitory effect on the human monoamine oxidase (hMAO) A and B isoforms. Different (un)substituted (hetero)aromatic substituents were linked to N1 of the hydrazone in order to establish robust structure–activity relationships. The results of the biological testing demonstrated that the presence of the hydrazothiazole nucleus bearing at C4 a phenyl ring functionalised at the meta position with a nitro group represents an important pharmacophoric feature to obtain selective and reversible human MAO-B inhibition for the treatment of neurodegenerative disorders. In addition, the most potent and selective MAO-B inhibitors were evaluated in silico as potential cholinesterase (AChE/BuChE) inhibitors and in vitro for antioxidant activities. The results obtained from molecular modelling studies provided insight into the multiple interactions and structural requirements for the reported MAO inhibitory properties.