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European Journal of Medicinal Chemistry
Vol. 113, 2016, Pages: 34–49

Synthesis of newer 1,2,3-triazole linked chalcone and flavone hybrid compounds and evaluation of their antimicrobial and cytotoxic activities

Rama Kant, Dharmendra Kumar, Drishti Agarwal, Rinkoo Devi Gupta, Ragini Tilak, Satish Kumar Awasthi, Alka Agarwal

Department of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi 221005, UP, India.


The present study was carried out in an attempt to synthesize a new class of antimicrobial and antiplasmodial agents by copper catalyzed click chemistry to afford 25 compounds 10–14(ae) of 1,4-disubstituted-1,2,3-triazole derivatives of chalcones and flavones. The structures of the newly synthesized compounds were established by elemental analysis, IR, 1H NMR, 13C NMR and Mass spectral data. The newly synthesized compounds were evaluated for their antibacterial activity against Gram positive bacteria (Staphylococcus aureusEnterococcus faecalis), Gram negative bacteria (Escherichia coliPseudomonas aeruginosaShigella boydiiKlebsiella pneumoniae) and antifungal activity against (Candida albicansCandida tropicalis,Candida parapsilosisCryptococcus neoformansDermatophyte) as well as molds (Aspergillus nigerAspergillus fumigatus). The antiplasmodial and cytotoxic activities of these compounds were also evaluated against human malaria parasite Plasmodium falciparum strain 3D7 and human hepato-cellular carcinoma cells (Huh-7), respectively. Compounds 10a10c10d12c and 14e showed promising antibacterial activity while compounds 10e11d11e12c13a13b13e14a and 14d showed good antifungal activity as compared to the corresponding standard drugs. Compound 10b was found to be the most active against Plasmodium falciparum while the remaining compounds showed moderate to weak antiplasmodial activity. However, cytotoxic activities of all compounds were found ineffective against Huh-7 cells.

Graphical abstract

Keywords: 1,2,3-Triazole; Chalcone; Antibacterial activity; Antifungal activity; Antiplasmodial activity; Cytotoxicity.

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