174502-91-1

Basic information

• Product Name: (2E)-2-[1-(pyridin-4-yl)ethylidene]hydrazinecarbothioamide
• CAS NO: 174502-91-1
• Molecular Formula: C₈H₁₀N₄S
• Molecular Weight: 194.2568
• Mol File: 174502-91-1.mol

Chemical Properties

• Boiling Point: 348.963°C at 760 mmHg
• Flash Point: 164.847°C
• Density: 1.282g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: (2E)-2-[1-(pyridin-4-yl)ethylidene]hydrazinecarbothioamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-2-[1-(pyridin-4-yl)ethylidene]hydrazinecarbothioamide(174502-91-1)
• EPA Substance Registry System: (2E)-2-[1-(pyridin-4-yl)ethylidene]hydrazinecarbothioamide(174502-91-1)

Safety Data

• Hazardous Substances Data: 174502-91-1(Hazardous Substances Data)

Upstream product

• 536-75-4 4-Ethylpyridine 
• 79-19-6 thiosemicarbazide 
• 1122-54-9 methyl (4-pyridyl) ketone 
• 350-03-8 methyl-3-pyridylketone 

Downstream Products

• 551921-12-1 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(1-(pyridin-4-yl)ethylidene)hydrazine 
• 1623025-83-1 3-benzyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazono)thiazolidin-4-one 
• 957761-53-4 4-phenyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazinyl)thiazole 

Relevant articles and documents

New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3- and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity

Metal semicarbazone and thiosemicarbazone complexes have attracted much attention due to their diverse biological activities. Because of the ability of ruthenium(II)-arene species to coordinate to different classes of ligands, they are suitable for fine-tuning chemical and pharmaceutical properties. Ruthenium(II) arene-complexes containing different types of ligands: namely caprylic hydrazide (a hydrazide with a long hydrocarbon chain), isonicotinic acid hydrazide (a hydrazide with an aromatic pyridine ring), thiosemicarbazones and semicarbazones (derived from the reaction of 3- and 4-acetylpyridine with either thiosemicarbazide or caprylic hydrazide), were obtained in the reaction of [(η6-p-cymene)RuCl2]2 with the corresponding ligands in a 1:2 or 1:2.2 molar ratio in methanol, ethanol or isopropanol with mild heating. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. The structure of complex 1 was determined by X-ray crystallography. Antiproliferative activity of the investigated complexes, determined for three human cancer cell lines (HeLa, A549 and LS-174) revealed moderate activity without significant influence on the matrix metallo-proteinases (MMP-2 and MMP-9) activity.

Synthesis and use of dioxime ligands for treatment of leukemia and colon cancer cells

Two new vicinal dioxime ligands containing thiosemicarbazone units (L1H2 and L2H2) were synthesized and characterized using 1H NMR, 13C NMR, heteronuclear multiple quantum correlation, mass, infrared and UV–visible spectroscopies, elemental analysis and magnetic susceptibility measurements. In addition, homotrinuclear nickel(II), copper(II) and cobalt(II) complexes with a metal-to-ligand ratio of 3:2 for L1H2 and L2H2 were prepared. Synthesis of nickel(II) complex containing a BF2 + bridge was carried out using a precursor hydrogen-bridged nickel(II) complex via the template effect. All metal–ligand complexes were tested against two human cancer cell lines (HL-60 and HT-29) for their antiproliferative and apoptotic activities. The results showed that [Co(L2H)2(H2O)2] and [Ni(L2H)2] exhibited the strongest antiproliferative activity with IpC50 values ranging between 5 and 10?μM, while [Co(L2H)2(H2O)2] and [Ni(L2H)2] both induced necrosis of HT-29 cells and 60 and 65% apoptosis in HL-60 cells, respectively.

Synthesis, anti-HIV activity, molecular modeling study and QSAR of new designed 2-(2-arylidenehydrazinyl)-4-arylthiazoles

Taking into consideration the eminence of 1,3-thiazoles in medicinal chemistry and in a view of procuring more pronounced biological contour, the synthesis of 2-(2-arylidenehydrazinyl)-4-arylthiazoles 6–43 was made possible by the cyclization reaction of thiosemicarbazones and α-bromoacetophenones. The thiosemicarbazones 5a-m were in turn synthesized from substituted benzaldehydes or acetophenones and thiosemicarbazide. Optimization of the reaction conditions was carried out in order to attain the target molecules in good yields. All the new compounds were evaluated in vitro for their antiviral activity against the replication of HIV-1 and HIV-2 in MT4 cells using a MTT assay. Screening results indicated that compounds 32–34 are the only compounds in the series inhibiting HIV-1 and HIV-2 replication in cell cultures with IC50 of >2.71, >2.19 and > 1.71 μM, respectively. The molecular docking of compounds 32 and 34 with some amino acids of human immunodeficiency virus reverse transcriptase (HIV RT) were also studied. The preliminary quantum structure-activity relationship (QSAR) among the newly synthesized congeners was obtained by two methods, Multiple Linear Regression (MRL) and Genetic Function Approximation (GFA).

Catalytic synthesis of organic cyclic carbonate through CO2 fixation and production of β-amino alcohol via ring opening of epoxides under green condition by polystyrene embedded Al(III) catalyst

Development of low cost, eco-friendly heterogeneous catalyst for the production of value added organic compounds has been drawn a considerable attention to the synthetic chemists in recent era. Keeping the above idea in our mind, we have design and synthesized a polymer anchored Al(III) composite from modified Merrifield resin. The composite was characterized properly by FT-IR spectra, SEM, EDAX, elemental analysis, ICP-AES and PXRD studies. The low cost material is very efficient heterogeneous catalyst for the production of fine organic chemicals such as organic cyclic carbonates and 2-amino alcohols under green and mild reaction conditions. Organic cyclic carbonates were synthesized through the insertion of carbon dioxide into epoxides at room temperature under solvent free condition. The developed protocol of catalytic synthesis of cyclic carbonates is sustainable, eco-friendly and cost-effective. Moreover atmospheric carbon dioxide is utilized here. Besides, the catalyst is very much efficient to produce 2-amino alcohol from ring opening of epoxides by nucleophilic attack of amine under solvent free condition and at room temperature. This polymer anchored Al(III) can be recovered and reused easily. The catalyst preserved its catalytic intensity even after use of eight successive catalytic cycles.

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.

Synthesis, biological evaluation and quantitative structure-active relationships of 1,3-thiazolidin-4-one derivatives. A promising chemical scaffold endowed with high antifungal potency and low cytotoxicity

With reference to recent studies reporting on the various biological properties of the thiazolidinone scaffold, we synthesized more than a hundred compounds characterized by a 1,3-thiazolidin-4-one nucleus derivatised at the C2 with a hydrazine bridge linked to (cyclo)aliphatic or hetero(aryl) moieties, and their N-benzylated derivatives. These molecules were assayed as potential anti-Candida agents and they were shown to possess comparable, and in some cases higher biological activity than well-established topical and systemic antimycotic drugs (i.e. clotrimazole, fluconazole, ketoconazole, miconazole, tioconazole, amphotericin B). Compounds endowed with the lowest MICs underwent further testing in order to assess their cytotoxic effect (CC50) on Hep2 cells, which demonstrated their relative safety. Finally, QSAR and 3-D QSAR models were used to predict putative chemical modifications of the 1,3-thiazolidin-4-one scaffold in order to design new and potential more active compounds against Candida spp.

Hydrazinyl arylthiazole based pyridine scaffolds: Synthesis, structural characterization, in?vitro α-glucosidase inhibitory activity, and in silico studies

Acarbose, miglitol, and voglibose are the inhibitors of α-glucosidase enzyme and being clinically used for the management of type-II diabetes mellitus. However, many adverse effects are also associated with them. So, the development of new therapeutic agents is an utmost interest in medicinal chemistry research. Current study is based on the identification of new α-glucosidase inhibitors. For that purpose, hydrazinyl arylthiazole based pyridine derivatives 1–39 were synthesized via two step reaction and fully characterized by spectroscopic techniques EI-MS, HREI-MS, 1H-, and 13C NMR. However, stereochemistry of the iminic bond was confirmed by NOESY. All compounds were subjected to in vitro α-glucosidase inhibitory activity and found many folds active (IC50 = 1.40 ± 0.01–236.10 ± 2.20 μM) as compared to the standard acarbose having IC50 value of 856.45 ± 5.60 μM. A limited structure-activity relationship was carried out in order to make a presumption about the substituent's effect on inhibitory activity which predicted that substituents of more negative inductive effect played important role in the activity as compared to the substituents of less negative inductive effect. However, in order to have a good understanding of ligand enzyme interactions, molecular docking study was also conducted. In silico study was confirmed that substituents like halogens (Cl) and nitro (NO2) which have negative inductive effect were found to make important interactions with active site residues.

Solvent selective phenyl selenylation and phenyl tellurylation of aryl boronic acids catalyzed by Cu(II) grafted functionalized polystyrene

A solvent-selective methodology for the phenyl selenylation and phenyl tellurylation of aryl boronic acids has been developed for the first time using a polymer supported Cu(II) catalyst. The catalyst was synthesized by anchoring Cu(OAc)2 onto a functionalized polystyrene with pyridine thiosemicarbazone ligand. It was then characterized properly by SEM, EDAX, FT-IR, TGA, and EPR experiments. The catalyst smoothly catalyzes phenyl selenylation of aryl boronic acids in water and phenyl tellurylation of aryl boronic acids in PEG-600, selectively. Thus a wide variety of unsymmetrical organodiaryl or aryl-heteroaryl selenides and tellurides have been synthesized by this protocol. The catalyst was recycled up to six runs without any appreciable loss of catalytic activity.

Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma

Antimitotic agents are widely used in cancer chemotherapy but the numerous side effects and the onset of resistance limit their clinical efficacy. Therefore, with the purpose of discovering more selective and efficient anticancer agents to be administered alone or in combination with traditional drugs, we synthesized a large library of 1,3,4-thiadiazoline analogues, maintaining the pharmacophoric structure of an antiproliferative compound known as K858: this is a new inhibitor of kinesin Eg5, able to induce the mitotic arrest in colorectal cancer cells and in xenograft ovarian cancer cells. We screened 103 compounds to assess their antiproliferative activity on PC3 prostate cancer cell line. Two derivatives, compounds 32 (corresponding to K858) and 33, have shown to be the most effective against prostate tumor cells and also towards two melanoma cell lines (SK-MEL-5 and SK-MEL-28) at low micromolar concentrations, confirming the pharmacological activity of this scaffold and revealing the potential role of 1,3,4-thiadiazolines in the management of cancer.

(Thiazol-2-yl)hydrazone derivatives from acetylpyridines as dual inhibitors of MAO and AChE: Synthesis, biological evaluation and molecular modeling studies

Several (thiazol-2-yl)hydrazone derivatives from 2-, 3- and 4-acetylpyridine were synthesized and tested against human monoamine oxidase (hMAO) A and B enzymes. Most of them had an inhibitory effect in the low micromolar/high nanomolar range, being derivatives of 4-acetylpyridine selective hMAO-B inhibitors also at low nanomolar concentrations. The structure-activity relationship, as confirmed by molecular modeling studies, proved that the pyridine ring linked to the hydrazonic nitrogen and the substituted aryl moiety at C4 of the thiazole conferred the inhibitory effects on hMAO enzymes. Successively, the strongest hMAO-B inhibitors were tested toward acetylcholinesterase (AChE) and the most interesting compound showed activity in the low micromolar range. Our results suggest that this scaffold could be further investigated for its potential multi-targeted role in the discovery of new drugs against the neurodegenerative diseases.