606969-03-3

Basic information

• Product Name: Imidazo[1,2-d]-1,2,4-thiadiazole, 3-[(4-methylphenyl)sulfonyl]-
• CAS NO: 606969-03-3
• Molecular Formula: C11H9N3O2S2
• Molecular Weight: 279.343
• Mol File: 606969-03-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Imidazo[1,2-d]-1,2,4-thiadiazole, 3-[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Imidazo[1,2-d]-1,2,4-thiadiazole, 3-[(4-methylphenyl)sulfonyl]-(606969-03-3)
• EPA Substance Registry System: Imidazo[1,2-d]-1,2,4-thiadiazole, 3-[(4-methylphenyl)sulfonyl]-(606969-03-3)

Safety Data

• Hazardous Substances Data: 606969-03-3(Hazardous Substances Data)

Upstream product

• 196196-59-5 2-butylimidazo[1,2-d]-1,2,4-thiadiazole-3(2H)-one 
• 19158-51-1 P-toluenesulfonyl cyanide 

Downstream Products

• 863983-23-7 N-[6-(imidazo[1,2-d][1,2,4]thiadiazol-3-ylamino)butyl]-2-nitrobenzenesulfonamide 
• 606969-34-0 N-[6-(imidazo[1,2-d][1,2,4]thiadiazol-3-ylamino)hexyl]-2-nitrobenzenesulfonamide 
• 606969-89-5 methyl N-imidazo[1,2-d][1,2,4]thiadiazol-3-yl-N-(6-{[(2-nitrophenyl)-sulfonyl]amino}hexyl)glycinate 
• 606969-11-3 2-Amino-N-[6-(imidazo[1,2-d][1,2,4]thiadiazol-3-ylamino)hexyl]benzenesulfonamide 

Relevant articles and documents

Synthesis of 3-substituted bicyclic imidazo[1,2-d][1,2,4]thiadiazoles and tricyclic benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazoles

A versatile synthetic route to potentially useful fused-ring [1,2,4]thiadiazole scaffolds (e.g., 7a and 10b) via exchange reactions of the precursor [1,2,4]thiadiazol-3-(2H)one derivatives (e.g., 6 and 9) with appropriately substituted nitriles (e.g., cyanogen bromide or p-toluenesulfonyl cyanide) under mild conditions is described. For example, the tricyclic 3-bromo [1,2,4]THD derivative (7a) underwent SNAr substitution with a variety of nucleophiles, which included amines, malonate esters and alcohols. Likewise, the bicyclic 3-p-tosyl [1,2,4]THD (10b) was employed as a template in reaction with diamines, and the resulting substituted diamines (e.g., 12a or 12e) were further selectively derivatized at the N1 and/or N2 positions in a linear fashion. The X-ray crystal structure of the 3-methyl bicyclic [1,2,4]THD (21) was obtained, and selective methylation at the N1 position via a protection-alkylation-deprotection protocol, as illustrated in Scheme 6, was confirmed. Alternatively, a short convergent synthesis of N1-functionalized derivatives from the reaction of 10b with appropriately substituted secondary amines was also developed. Hence, these synthetic strategies were advantageously exploited to provide access to a variety of diversely derivatized 3-substituted fused-ring [1,2,4]thiadiazole derivatives.

Sulfonamide derivatives of 3-substituted imidazo[1,2-D]-1,2,4-thiadiazoles and 3-substituted-[1,2,4]thiadiazolo[4,5-A]benzimidazole as inhibitors of fibrin cross-linking and transglutaminases

A method of inhibiting the activity of transglutaminases containing a cysteine residue comprising administering to a mammal an effective amount of a sulfonamide derivative of imidazo[1,2-d]-1,2,4-thiadiazoles sufficient to inhibit the activity.