Scheme 1
Synthesis process for 2-iodophenylimino-5-arylidenethiazolidin-4-one. The initial reactant, 2-iodoaniline, underwent the first acylation with chloroacetic acid, a second cyclization with ammonium thiocyanate, and a final aldol condensation with various aromatic aldehydes.
Table 1
Antimicrobial activity of the synthesized compounds, 3A–3L, on various strains of bacteria and fungi
| |||||||||
|---|---|---|---|---|---|---|---|---|---|
| Structure | Name | R | Bacteria | Fungi | |||||
| E. coli | P. aeruginosa | E. faecalis | S. aureus | MRSA | C. albicans | A. niger | |||
| 2-(2-Iodophenylimino)-5- | |||||||||
| 3A | (4-methoxybenzylidene)thiazolidin- | 4”-OCH3 | − | − | − | >1024 | >1024 | − | − |
| 4-one | |||||||||
| 2-(2-Iodophenylimino)-5- | |||||||||
| 3B | (4-chlorobenzylidene)thiazolidin- | 4”-Cl | − | − | − | 8 | 4 | − | − |
| 4-one | |||||||||
| 2-(2-Iodophenylimino)-5- | |||||||||
| 3C | (2,4-dichlorobenzylidene)thiazoli- | 2”-Cl | − | − | − | >1024 | >1024 | − | − |
| din-4-one | 4”-Cl | ||||||||
| 2-(2-Iodophenylimino)-5- | 4”-OH | ||||||||
| 3D | (4-hydroxy-3-methoxybenzylidene) | 3”-OCH | − | − | − | 16 | 16 | − | − |
| thiazolidin-4-one | 3 | ||||||||
| 2-(2-Iodophenylimino)-5- | |||||||||
| 3E | (4-fluorobenzylidene)thiazolidin- | 4”-F | − | − | − | 8 | 8 | − | − |
| 4-one | |||||||||
| 3F | 2-(2-Iodophenylimino)-5- | − | − | − | >1024 | >1024 | − | − | |
| benzylidenethiazolidin-4-one | |||||||||
| 2-(2-Iodophenylimino)-5- | |||||||||
| 3G | (4-methylbenzylidene)thiazolidin- | 4”-CH3 | − | − | − | >1024 | 128 | − | − |
| 4-one | |||||||||
| 2-(2-Iodophenylimino)-5- | |||||||||
| 3H | (4-nitrobenzylidene)thiazolidin- | 4”-NO2 | − | − | − | 8 | 8 | − | − |
| 4-one | |||||||||
| 2-(2-Iodophenylimino)-5- | |||||||||
| 3I | (2-nitrobenzylidene)thiazolidin- | 2”-NO2 | − | − | >1024 | 8 | 32 | − | − |
| 4-one | |||||||||
| 2-(2-Iodophenylimino)-5- | |||||||||
| 3J | (2-hydroxybenzylidene)thiazolidin- | 2”-OH | − | − | − | >1024 | >1024 | − | − |
| 4-one | |||||||||
| 2-(2-Iodophenylimino)-5- | 2”-OH | ||||||||
| 3K | (5-bromo-2-hydroxybenzylidene) | 5”-Br | − | − | − | 64 | 64 | − | − |
| thiazolidin-4-one | |||||||||
| 2-(2-Iodophenylimino)-5- | |||||||||
| 3L | (4-dimethylaminobenzylidene) | 4”-N(CH3)2 | − | − | − | − | – | − | − |
| thiazolidin-4-one | |||||||||
| PC | Cephalexin | 32 | 4 | 32 | |||||
[i] The tests were performed in duplicate; (–) indicates negative result (clear zone diameter was less than that for the negative control, DMSO); the number indicates the mean of the MIC (mg/mL) of compounds active against specific microbes.
A. niger, Aspergillus niger; C. albicans, Candida albicans; DMSO, dimethylsulfoxide; E. coli, Escherichia coli; E. faecalis, Enterococcus faecalis; MIC, minimum inhibitory concentration; P. aeruginosa, Pseudomonas aeruginosa; PC, positive control; S. aureus, Streptococcus aureus.