TITLE:
Synthesis, Characteristic and Antimicrobial Activity of Some New Spiro[indol-thiazolidon-2,4-diones] and Bis(5-fluorospiro[indoline-3,2’-thiazolidine]-2,4’-dione) Probes
AUTHORS:
Abeer N. Al-Romaizan
KEYWORDS:
Synthesis, Spiroindoline-Thiazolidine, Mercaptoacetic Acid, Antimicrobial, 5-Substituted Isatin, Sulfanilamide
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.10 No.2,
May
20,
2020
ABSTRACT: In a search for new antimicrobial agents, some new spiro[indol-thiazolidon- 2,4-diones] (6a-c) were synthesized by condensation of 5-substituted isatins 1 with sulfanilamide in MeOH, followed by aroylation with p-nitrobenzoyl chloride in DMF to get compounds 4a-c. Cycloaddition of 4a-c with thioglycolic acid in a dry non-polar solvent (dioxane) gave the targets 6a-c. Also, bis(5-fluorospiro[indoline-3,2’-thiazolidine]-2,4’-dione) (9) was synthesized by condensation of 5-fluoroindoline-2,3-dione with benzene-1,4-diamine (2:1 by mol) in MeOH, which followed by cycloaddition with thioglycolic acid in dioxane gave compound 8. Acylation of the later with 2,2,2-trifluoroacetic anhydride in THF has yielded the target 9. Structures of the products have been deduced from their elemental analysis and spectral data. The in vitro antimicrobial activity of the new systems 6a-c, and 9 was tested.