825606-04-0

Basic information

• Product Name: 3-(4-fluorophenyl)-6-[(4-methoxyphenoxy)methyl][1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
• Synonyms: 3-(4-fluorophenyl)-6-[(4-methoxyphenoxy)methyl][1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
• CAS NO: 825606-04-0
• Molecular Formula: C17H13FN4O2S
• Molecular Weight: 356.3741232
• Mol File: 825606-04-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(4-fluorophenyl)-6-[(4-methoxyphenoxy)methyl][1,2,4]triazolo[3,4-b][1,3,4]thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-fluorophenyl)-6-[(4-methoxyphenoxy)methyl][1,2,4]triazolo[3,4-b][1,3,4]thiadiazole(825606-04-0)
• EPA Substance Registry System: 3-(4-fluorophenyl)-6-[(4-methoxyphenoxy)methyl][1,2,4]triazolo[3,4-b][1,3,4]thiadiazole(825606-04-0)

Safety Data

• Hazardous Substances Data: 825606-04-0(Hazardous Substances Data)

Upstream product

• 456-22-4 4-Fluorobenzoic acid 
• 61019-29-2 C₈H₆FN₂OS₂^(1-)*K⁽¹⁺⁾ 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 1877-75-4 2-(4-methoxyphenoxy)acetic acid 
• 61019-25-8 4-amino-5-(3-fiuorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiol 
• 90172-63-7 1-(p-fluorophenylcarbonyl)imidazole 

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.