Microwave-assisted synthesis and antimicrobial activity of some imidazo[2,1-b][1,3,4]thiadiazole derivatives

Medicinal Chemistry Research
2012.0

Abstract

A simple and efficient method was developed for the synthesis of 2,6-disubstituted-imidazo[2,1-b][1,3,4] thiadiazoles under microwave (MW) activation using 2-amino-5-substituted-1,3,4-thiadiazoles and appropriate bromo ketones as materials. All reactions demonstrated the benefits of MW reactions: convenient operation, short reaction time, and good yields. All derivatives were characterized by IR, NMR, and Mass spectroscopy. Antibacterial and antifungal activity was performed using cup plate method against Staphylococcus aureus, Klebsiella, and Candida albicans microorganisms. 2-(4-nitro benzyl)-6-(4 bromo phenyl)imidazo[2,1-b][1,3,4]thiadiazole (4Ce) was the only derivative which showed activity against Klebsiella at low micromolar concentration (5 lg/ml) with moderate zone of inhibition. And 2-(4-nitro benzyl)-6- (4-fluoro phenyl)imidazo[2,1-b][1,3,4]thiadiazole (4Cf) as the most potent antifungal active derivative at 50 lg/ml against C. albicans on comparison to standard fluconazole.

Knowledge Graph

Similar Paper

Microwave-assisted synthesis and antimicrobial activity of some imidazo[2,1-b][1,3,4]thiadiazole derivatives
Medicinal Chemistry Research 2012.0
Microwave-assisted synthesis and antimicrobial screening of new imidazole derivatives bearing 4-thiazolidinone nucleus
Medicinal Chemistry Research 2013.0
Synthesis and biological evaluation of novel substituted 1,3,4-thiadiazole and 2,6-di aryl substituted imidazo [2,1-b] [1,3,4] thiadiazole derivatives
European Journal of Medicinal Chemistry 2014.0
TDAE-assisted synthesis of new imidazo[2,1- b ]thiazole derivatives as anti-infectious agents
European Journal of Medicinal Chemistry 2010.0
Conventional and microwave assisted synthesis of Some new N-[(4-oxo-2-substituted aryl −1, 3-thiazolidine)-acetamidyl]-5-nitroindazoles and its antimicrobial activity
European Journal of Medicinal Chemistry 2010.0
Synthesis and evaluation of antibacterial and antitubercular activities of some novel imidazo[2,1-b][1,3,4]thiadiazole derivatives
Medicinal Chemistry Research 2013.0
Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety
European Journal of Medicinal Chemistry 2010.0
Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazole derivatives
European Journal of Medicinal Chemistry 2009.0
Microwave assisted synthesis and structure–activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents
European Journal of Medicinal Chemistry 2011.0
Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: Derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety
European Journal of Medicinal Chemistry 2013.0