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Synthesis, characterization and in vitro antimicrobial activity of novel 2-thioxo-4-thiazolidinones and 4,4'-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfones.
- Source :
-
European journal of medicinal chemistry [Eur J Med Chem] 2009 Oct; Vol. 44 (10), pp. 4148-52. Date of Electronic Publication: 2009 May 19. - Publication Year :
- 2009
-
Abstract
- 2-Thioxo-4-thiazolidinones (3a,b) were achieved by cyclocondensation of isothiocyanatosulfonamides (1a,b) with sulfanylacetic acid at reflux temperature in dioxane in the presence of triethylamine. Compound (3a) was exploited to synthesize the versatile hitherto unknown 2-thioxo-4-thiazolidinones (5-10) via its reaction with some electrophiles. Cyclization of 4,4'-diisothiocyanate diphenylsulfone (11) with sulfanylacetic acid furnished 4,4'-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfone (12) which on treatment with excess 4-methoxybenzaldehyde in refluxing dioxane in the presence of piperidine yielded the bisbenzylidene derivative (13). The novel synthesized compounds were characterized by IR, (1)H NMR and mass spectral studies. All the synthesized compounds were screened in vitro for their antibacterial and antifungal activities.
- Subjects :
- Anti-Bacterial Agents chemical synthesis
Antifungal Agents chemical synthesis
Bacteria drug effects
Fungi drug effects
Isothiocyanates chemical synthesis
Microbial Sensitivity Tests
Molecular Structure
Structure-Activity Relationship
Thiazolidines chemical synthesis
Anti-Bacterial Agents chemistry
Anti-Bacterial Agents pharmacology
Antifungal Agents chemistry
Antifungal Agents pharmacology
Isothiocyanates chemistry
Isothiocyanates pharmacology
Thiazolidines chemistry
Thiazolidines pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1768-3254
- Volume :
- 44
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- European journal of medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 19540629
- Full Text :
- https://doi.org/10.1016/j.ejmech.2009.05.005