Synthesis of New [3-Nitro-2-Oxo-2H-Chromen-4-Ylamino)-Phenyl]-Phenyl-Triazolidin-4-Ones and Their Antibacterial Activity
Synthesis of New [3-Nitro-2-Oxo-2H-Chromen-4-Ylamino)-Phenyl]-Phenyl-Triazolidin-4-Ones and Their Antibacterial Activity

Summary/Abstract: A series of reactions that result in the synthesis of novel thiazolidynones based on 4-chloro-3-nitrobenzopyran-2-one is presented in this study. During the condensation reaction of 4-chloro-3-nitrobenzopyran-2-one 2 and benzene-1,4-diamine, 4-(4-Amino-phenylamino)-3-nitro-chromen-2-one 3 is synthesized in high yield. By catalytic condensation of product 3 and benzaldehyde, salicylaldehyde and 3-nitrobenzaldehyde, novel derivatives of 4-[4-(Benzylidene-amino)-phenylamino]-3-nitrobenzopyran-2-one, 4(a-c), as condensation products are synthesized. In the following series of reactions, by cyclization of the products 4(a-c) and 2-mercaptopropionic acid, corresponding substituted thiazolidinones 5(a-c) are synthesized. Determination of structure of the synthesized products is done on the basis of spectrometric data. Compounds 4(a-c) and 5(a-c) are examined for their antibacterial activity against S. aureus, E. coli and Klebsiella by measuring the zones of inhibition around the disks impregnated with the corresponding solutions of compounds in N,N-DMF concentration 2 mg/mL, 4 mg/mL and 6 mg/mL. Compounds of series 4 have shown moderate antibacterial activity against these microorganisms, whereas compounds of series 5 have shown significant activity. The impact of substitutions in antmicrobial activity is also explored.

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