SYNTHESIS CHARACTERISATION AND BIOLOGICAL EVALUATION OF (3Z, 4Z)-3, 4-BIS (SUBSTITUTED PHENYL BENZYLIDINE)-1-(4-SUBTITUTED PHENYL) PYROLIDINE-2, 5-DIONE
Objective: The present study focuses on synthesis and characterization of new series of bis-chalcone derivatives from cyclic imides and evaluating its antimicrobial activity against a pathogenic microorganism.
Methods: The substituted cyclic imides 4-methyl phenyl pyrrolidine 2,5 dione 1 and 4-methoxy phenyl pyrrolidine 2,5 dione 2 were synthesized from succinic acid and primary aromatic amines. These cyclic imides condensed with substituted benzaldehydes in the presence of acetic acid furnished bis-heterocyclic chalcones and characterized by FT-IR, 1H NMR and also microbial activity was determined using the disc diffusion method.
Results: The antimicrobial activity of bis-heterocyclic chalcones was tested against selective pathogens and the zone of inhibition was observed in E. coli, C. albicans and A. niger at 100Âµg/ml concentration.
Conclusion: The compound (3Z,4Z)-3,4-bis-(2-hydroxybenzylidine)-1-p-tolylpyrrolidine-2,5-dione (3b) with methyl and hydroxyl substituent on benzene ring exhibited good antibacterial activity against E. coli and potent antifungal activity against C. albicans and A. niger.
Keywords: Succinic acid, Cyclic imides, Pyrrolidine-2,5-dione, Bis-chalcone
Kartizsky AR, Pozharskii AF. Handbook of heterocyclic Chemistry. Edition 2nd. Pergamum-NY; 2000.
Solankee AN, Patel GA. Synthesis characterization and antibacterial activity of some novel isoxazoles, pyrimidinthiones, and pyrimidinones. Int J Pharm Biol Sci 2011;2:163-9.
Hatem A, Abdel AA, Khalid A. Microwave-assisted Synthesis of Novel 3,4-Bis-chalcone-N-aryl pyrazoles and their anti-inflammatory activity. Chin J Chem Soc 2011;58:863-8.
Singh S, Sharm PK, Kumar N, Dudhe R. Antioxidant activity of 2-hydroxyacetophenone Chalcone. J Adv Sci Res 2011;2:37-41.
Prasadarao K, Lusirani Susuma AJ, Mohan S. Synthesis characterization and antibacterial activity of few chalcone. Int J Pharm Biol Sci 2012;34:781â€“8.
Correa R, Filho VC, Rosa PW, Pereira CI, Schlemper V, Nunes RJ. Synthesis of new succinimides and sulfonated derivatives with analgesic action in mice. Pharmacogn Commun 1997;32:67-1.
Singh A, Rana AC. Synthesis and anticonvulsant activity of 1-(4, 5-dihydro-5-phenyl-3-(phenylamino) pyrazol-1-yl) ethanone derivatives. J Chem Pharm Res 2010;21:505-11.
Selvi RS, Nanthini R, Sukanyaa G. Synthesis and in vitro evaluation of copolyester chalcone derivatives as potential anticancer agents. Int J Basic Appl Med Sci 2011;1:18-22.
Patil MM, Rajput SS. Succinimides synthesis reaction and biological activity. Int J Pharm Pharm Sci 2014;6:8-14.
Rajput SS. Synthesis and characterization of bis-heterocyclic derivatives of 1-3-Chlorophenyl-Pyrrolidine-2, 5-dione. Int J Appl Pharm Biol Chem 2012;12:242-6.
Dhivare RS, Rajput SS. Synthesis and antimicrobial activity of five-membered cyclic imide derivatives of mono di and tri-substituted aromatic amines and naphthyl amine. World J Pharm Res 2014;4:1650-8.
Vanati P, Rajiv P, Rajeshwari S. Eichhornia mediated copper oxide nanoparticles in vitro analysis of antimicrobial activity. Int J Pharm Pharm Sci 2015;7:422-4.
Rao AS, Siman L, Srinivasan KK, Moorkoth S, Haleem ZA, Jadon SS, et al. Synthesis and in vitro antimicrobial evaluation of 5-Acetamido-2-Hydroxy Chalcone derivative. Res J Chem Sci 2014;4:56-9.