57772-04-0

Basic information

• Product Name: 2-methyl-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole
• Synonyms: 2-methyl-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole
• CAS NO: 57772-04-0
• Molecular Weight: 229.305
• Mol File: 57772-04-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-methyl-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole(57772-04-0)
• EPA Substance Registry System: 2-methyl-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole(57772-04-0)

Safety Data

• Hazardous Substances Data: 57772-04-0(Hazardous Substances Data)

Upstream product

• 619-41-0 4-(bromoacetyl)toluene 
• 108-33-8 5-methyl-1,3,4-thiadiazol-2-amine 

Downstream Products

• 57772-16-4 2-methyl-5-(4-nitro-phenylazo)-6-p-tolyl-imidazo[2,1-b][1,3,4]thiadiazole 

Relevant articles and documents

Ionic liquid-promoted one-pot synthesis of thiazole-imidazo[2,1-b][1,3,4]thiadiazole hybrids and their antitubercular activity

In this paper, we report the facile and efficient one-pot three-component synthesis of 1-((6-phenylimidazo[2,1-b][1,3,4]thiadiazol-5-yl)methylene)-2-(4-phenylthiazol-2-yl)hydrazine derivatives (5a-w) using an ionic liquid, namely 1-butyl-3-methylimidazolium bromide ([Bmim]Br). The compounds were screened for their in vitro antimycobacterial activity against Mycobacterium tuberculosis. Compound 5s showed the highest inhibitory activity with an MIC of 6.03 μM which is slightly lower than the MIC values of standard drugs ethambutol (15.3 μM) and ciprofloxacin (9.4 μM). Four other compounds of the series viz.5e, 5i, 5t and 5w also showed significant inhibitory activity with MIC values in the range of 11.7-13.9 μM. The structure-activity relationship revealed that the trifluoromethyl substitution at position-2 and p-chlorophenyl substitution at position-6 of the imidazo[2,1-b][1,3,4]thiadiazole ring enhanced the inhibitory activity. Also, the methyl, methoxy, fluoro or nitro substituents on the thiazole ring enhanced the activity of the compounds. None of the active compounds were toxic to a normal cell line (NIH 3T3), which signifies the lack of general cellular toxicity of the molecules. In silico molecular docking studies revealed the favourable interaction of the potent compounds with the target enzymes InhA and CYP121.

One-pot synthesis of new triazole - Imidazo[2,1-b][1,3,4]thiadiazole hybrids via click chemistry and evaluation of their antitubercular activity

A new series of triazole-imidazo[2,1-b][1,3,4]thiadiazole hybrids (6a-s, 7a) were designed by a molecular hybridisation approach and the target molecules were synthesized via one pot click chemistry protocol. All the intermediates and final molecules were

Potassium carbonate-mediated green and efficient synthesis of imidazo[2,1-b]-1,3,4-thiadiazoles using PEG as solvent

Polyethylene glycol (PEG) was found to be an inexpensive nontoxic and effective medium for the synthesis of imidazo[2,1-b]-1,3,4-thiadiazoles in the presence of potassium carbonate as a green base in high yields. In addition, the solvent system can be recovered and reused, making this protocol economically and potentially viable.