3115-21-7

Basic information

• Product Name: Hydrazinecarbothioamide, 2-(1-(4-pyridinyl)ethylidene)- (9CI)
• Synonyms: Hydrazinecarbothioamide, 2-(1-(4-pyridinyl)ethylidene)- (9CI);1-[1-(4-Pyridyl)ethylidene]thiosemicarbazide;1-[1-(4-Pyridyl)-ethylidene]thiosemicarbazide;Methyl 4-pyridyl ketonethiosemicarbazone;Methyl(4-pyridinyl) ketone thiosemicarbazone
• CAS NO: 3115-21-7
• Molecular Formula: C₈H₁₀N₄S
• Molecular Weight: 194.26
• Mol File: 3115-21-7.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 349°Cat760mmHg
• Flash Point: 164.8°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: Hydrazinecarbothioamide, 2-(1-(4-pyridinyl)ethylidene)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Hydrazinecarbothioamide, 2-(1-(4-pyridinyl)ethylidene)- (9CI)(3115-21-7)
• EPA Substance Registry System: Hydrazinecarbothioamide, 2-(1-(4-pyridinyl)ethylidene)- (9CI)(3115-21-7)

Safety Data

• Hazardous Substances Data: 3115-21-7(Hazardous Substances Data)

Usage

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

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

• 1053661-97-4 N-[1-(4-pyridyl)ethylidene]-N'-[4-(2-hydroxy-5-methoxyphenyl)thiazol-2-yl]hydrazine 
• 957761-57-8 1-(1-(pyridin-4-yl)ethylidene)-2-(4-p-tolylthiazol-2-yl)hydrazine 
• 957761-55-6 1-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(1-(pyridin-4-yl)ethylidene)hydrazine 
• 1383115-03-4 1-(4-(4-iodophenyl)thiazol-2-yl)-2-(1-(pyridin-4-yl)ethylidene)hydrazine 
• 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 

Relevant articles and documents

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).

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.