SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL STUDIES OF NEW THIAZOLIDINONES
Masrat Jan, Shafia Mir, Praveen Kumar, Ayaz Mahmood Dar
A new series of acetophenone appended thiazolidinones (5-8) were synthesized by the reaction of acetophenone and its derivatives (1-4) with thiosemicarbazide and merceptoacetic acid in absolute ethanol in one pot manner. The striking feature of this reaction is the formation of thiosemicarbazine in situ which in turn undergoes the cyclization with mercepto acetic acid, leading to the formation of new thiazolidinones. Thus the thiazolidinone ring closes at carbonyl carbon, by the attack of sulfur of mercaptoacetic acid moiety, preferentially from the front (β, axial) so that the nitrogen has an equatorial orientation (α, equatorial) to avoid steric repulsion, giving minimum steric hindrance. The new compounds were characterized by spectral (IR, 1H NMR, 13C NMR, MS) and analytical methods. The new compounds were screened for antimicrobial activity against various strains of bacteria and fungi, during which the new compounds depicted potential antimicrobial behaviour.
Keywords: Thiosemicarbazide and merceptoacetic.
[Full Text Article]