133847-09-3

Basic information

• Product Name: 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazole, 6-[(4-chlorophenoxy)methyl]-3-(4-pyridinyl)-
• CAS NO: 133847-09-3
• Molecular Formula: C15H10ClN5OS
• Molecular Weight: 343.79100
• Mol File: 133847-09-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazole, 6-[(4-chlorophenoxy)methyl]-3-(4-pyridinyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazole, 6-[(4-chlorophenoxy)methyl]-3-(4-pyridinyl)-(133847-09-3)
• EPA Substance Registry System: 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazole, 6-[(4-chlorophenoxy)methyl]-3-(4-pyridinyl)-(133847-09-3)

Safety Data

• Hazardous Substances Data: 133847-09-3(Hazardous Substances Data)

Upstream product

• 55-22-1 pyridine-4-carboxylic acid 
• 90322-87-5 1-isonicotinoyl-1H-imidazole 
• 61019-32-7 potassium 4-pyridinyldithiocarbazate 
• 54-85-3 isoniazid 
• 36209-51-5 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol 
• 122-88-3 4-Chlorophenoxyacetic acid 

Relevant articles and documents

SAR studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents

Shikimate dehydrogenase, an essential protein for the biosynthesis of the chorismate end product, is a highly promising therapeutic target, especially for the discovery and development of new-generation anti-TB agents. Following up the identification of one lead 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole (1), targeting Mt SD in our previous study, an extensive SAR study for optimization of the lead compound was performed through systematic modification of the 3 and 6 positions. This study has successfully led to the discovery of two highly potent advanced leads 6d-4, 6c-4 and several other compounds with comparable potencies (6d-4, MIC-H37Rv = 0.5 μg mL-1; MIC-MDRTB = 4.0 μg mL-1; MIC-RDRTB = 0.5 μg mL-1; Mt SD-IC50 = 14.20 μg mL-1; and 6c-4, MIC-H37Rv = 0.5 μg mL-1; MIC-MDRTB = 4.0 μg mL-1; MIC-RDRTB = 1.0 μg mL-1; Mt SD-IC50 = 6.82 μg mL-1). These advanced lead compounds possess a para-halogen phenyl at the 3 position. In vitro Mt SD inhibitory assay indicates that Mt SD is the target for their antitubercular activity. Moreover, the BacT/ALERT 3D liquid culture technology and in vitro Mt SD inhibitory assay were initially applied.

Synthesis and biological activity of some triazolothiadiazoles

The synthesis of a series of novel 3-pyridyl-6-aryl-s-triazolo[3,4-b]-[1,3, 4]-thiadiazoles is described. Fourteen new compounds were synthesized and characterized by spectral and elemental analyses. Some compounds were screened for antibacterial activity against S. aureus, E. coli, B. subtilis and P. aeruginosa. Compounds containing aryl substituents at position 6 and the 1,2,4-triazole moiety at position 1 or 2 showed reasonable antibacterial activity.