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Highly Diastereoselective Syntheses of Spiro‐Oxindole Dihydrofuran Derivatives in Aqueous Media and Their Antibacterial Activity
Author(s) -
Gupta Naveen,
Bhojani Gopal,
Tak Rajkumar,
Jakhar Ajay,
Khan Noorul H.,
Chatterjee Shruti,
Kureshy Rukhsana I.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702314
Subject(s) - bacillus subtilis , shigella flexneri , chemistry , minimum inhibitory concentration , minimum bactericidal concentration , shigella boydii , escherichia coli , bacillus licheniformis , pseudomonas fluorescens , vibrio cholerae , proteus vulgaris , microbiology and biotechnology , bacteria , organic chemistry , biology , biochemistry , antimicrobial , genetics , gene
A series of substituted spiro‐oxindole dihydrofuran ring derivatives were synthesized in good yields up to 94% and excellent diastereoselectivity ≥99% by simple tandem Michael ‐ cyclization in aqueous media using DABCO (1,4‐diazabicyclo[2.2.2]octane) as a catalyst and SDS (sodium dodecyl sulfate) as a promoter at ambient temperature. These molecules displayed promising antibacterial activity in vitro against pathogenic strains viz Vibrio cholerae , Escherichia coli , Bacillus subtilis , Bacillus licheniformis , Pseudomonas fluorescens , Salmonella enterica , Shigella flexneri and Shigella boydii with MIC (minimum inhibitory concentration), MBC (minimum bactericidal concentration) and IC50 (inhibitory concentration) values better than the standard antibiotic ampicillin.