176037-42-6

Basic information

• Product Name: 2-(4-1,2,3-THIADIAZOLYL)PYRIDINE
• Synonyms: 2-(4-1,2,3-THIADIAZOLYL)PYRIDINE;4-pyridin-2-ylthiadiazole
• CAS NO: 176037-42-6
• Molecular Formula: C7H5N3S
• Molecular Weight: 163.2
• Mol File: 176037-42-6.mol

Chemical Properties

• Melting Point: 163 °C
• Boiling Point: 307.4±34.0 °C(Predicted)
• Appearance: /
• Density: 1.317±0.06 g/cm3(Predicted)
• PKA: -0.14±0.19(Predicted)
• CAS DataBase Reference: 2-(4-1,2,3-THIADIAZOLYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-1,2,3-THIADIAZOLYL)PYRIDINE(176037-42-6)
• EPA Substance Registry System: 2-(4-1,2,3-THIADIAZOLYL)PYRIDINE(176037-42-6)

Safety Data

• Hazardous Substances Data: 176037-42-6(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic compound

Structural components

Pyridine ring and 1,2,3-thiadiazole ring

Potential applications

Medicinal chemistry, drug development, chelating agent for metal ions, inhibitor of certain enzymes, antimicrobial, antifungal, and anti-inflammatory properties.

Upstream product

• 1122-62-9 2-acetylpyridine 
• 1402672-07-4 C₁₆H₂₄N₅O₂S⁽¹⁺⁾*CF₃O₃S^(1-) 
• 1261591-06-3 N'-[(1E)-1-(pyridin-2-yl)ethylidene]-2-(quinolin-8-yloxy)acetohydrazone 
• 14534-93-1 2-acetylpyridine semicarbazone 
• 85748-62-5 2-acetyl-pyridine ethoxycarbonylhydrazon 

Relevant articles and documents

The 1,2,3-thiadiazole route to new vinylogue tetrathiafulvalenes

Cleavage of 1,4-dithiafulvene-substituted 1,2,3-thiadiazoles with base and dimerisation of the resulting alkyne-1-thiolate gives new tetrathiafulvalene-type vinylogue extended π-donors in a one pot reaction. The solvent-/base-system used (acetonitrile/NaH) was optimised for the synthesis of 1,3-dithiole-2-thiones via this route. Efficient synthesis of the important 4-formyl-1,3-dithiol-2-thione and its coupling to 2,6(7)-bisformyltetrathiafulvalene is presented. Preparation of a number of new 1,4-dithiafulvenes are reported.

Regio- and stereoselective synthesis of thiazoline derivatives via the thioketene-induced ring expansion of aziridines

Metal-free thioketene-induced ring expansion of aziridines gave 4-alkylthiazolines stereospecifically from 2-alkylaziridines through an intramolecular substitution at the less substituted ring carbon and 5-arylthiazolines stereoselectively from 2-arylaziridines via tandem ring cleavage and formation through intimate ion-pair intermediates after nucleophilic addition of aziridines to thioketenes generated from 4-substituted 1,2,3-thiadiazoles in the presence of a base.

TBAI-Catalyzed Reaction between N-Tosylhydrazones and Sulfur: A Procedure toward 1,2,3-Thiadiazole

A TBAI-catalyzed reaction between N-tosyl hydrazone and sulfur was developed, leading to 1,2,3-thiadiazoles in moderate to good yields. It represents a facile and practical procedure to access thiadiazole under metal-free conditions. This procedure serves

Ionic liquid as soluble support for synthesis of 1,2,3-thiadiazoles and 1,2,3-selenadiazoles

A convenient synthesis of 1,2,3-thiadiazoles and 1,2,3-selenadiazoles was achieved using an ionic liquid as a novel soluble support. Ionic liquid-supported sulfonyl hydrazine was synthesized and reacted with a number of ketones to afford the corresponding ionic liquid-supported hydrazones that were converted to 1,2,3-thiadiazoles in the presence of thionyl chloride. The reaction of ionic liquid-supported hydrazones with selenium dioxide in acetonitrile afforded 1,2,3-selenadiazoles. The advantages of this methodology were the ease of workup, simple reaction conditions, and high purity.

Synthesis, characterization, antiamoebic activity and cytotoxicity of novel 2-(quinolin-8-yloxy) acetohydrazones and their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives)

A series of 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives were synthesized by the cyclization of novel 2-(quinolin-8-yloxy) acetohydrazones. In vitro antiamoebic activity was performed against HM1: IMSS strain of Entamoeba histolytica. The results showed that all the 2-(quinolin-8-yloxy) acetohydrazones were more active than their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives). SAR showed that the compounds having quinoline ring and hydrazone linkage with free N-H group are responsible for higher antiamoebic activity. The cytotoxic studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds were nontoxic at the concentration range of 1.56-50 μM.