A facile 1,3-dipolar cycloaddition of azomethine ylides to 2-arylidene-1,3-indanediones: synthesis of dispiro-oxindolylpyrrolothiazoles and their antimycobacterial evaluation |
| |
| Authors: | Maheswari Shanmugavel Uma Balamurugan Kamaraj Perumal Subbu Yogeeswari Perumal Sriram Dharmarajan |
| |
| Affiliation: | Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, Tamil Nadu, India. |
| |
| Abstract: | A facile 1,3-dipolar cycloaddition of azomethine ylide generated in situ from the reaction of 1,3-thiazolane-4-carboxylic acid and isatin to 2-arylidene-1,3-indanediones furnished novel dispiro-oxindolylpyrrolothiazoles regio- and stereo-selectively in moderate to good yields (60-92%). In vitro antitubercular screening of 27 compounds against Mycobacterium tuberculosis H37Rv (MTB) disclosed that spiro[5.3']-5'-nitrooxindolespiro-[6.3″]-1H-inden-1″,3″(2H)-dione-7-(4-bromophenyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole has the maximum potency with a minimum inhibitory concentration (MIC) of 1.4 μM against MTB, being 3.4 and 5.4 times more potent than ciprofloxacin and ethambutol, respectively. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect PubMed 等数据库收录！ |
|
