Synthesis of new olefin chalcone derivatives as antitumor, antioxidant and antimicrobial agents

• Published in: Medicinal chemistry research 2012-12, Vol.21 (12), p.4512-4522
• Main Authors: Bandgar, Babasaheb P., Jalde, Shivkumar S., Adsul, Laxman K., Shringare, Sadanand N., Lonikar, Shrikant V., Gacche, Rajesh N., Dhole, Nagesh A., Nile, Shivraj H., Shirfule, Amol L.
• Format: Article
• Language: English
• Subjects: Biochemistry; Biomedical and Life Sciences; Biomedicine; Cell Biology; Original Research; Pharmacology/Toxicology
• ISSN: 1054-2523; 1554-8120
• DOI: 10.1007/s00044-012-9979-z

Chalcone is a unique template that is associated with several biological activities. Claisen–Schmidt condensation of olefin aldehyde 3 and various mono, disubstituted and heterocyclic acetophenones afforded novel olefin chalcones. Synthesized compounds were subjected for ADME prediction by computational method which revealed that these molecules can be considered as a potential drug. Out of the 21 compounds screened, compounds 5u , 5g , 5c and 5e have shown significant cytotoxicity against Hep 3BPN 7, compounds 5j , 5i , 5n and 5o showed good cytotoxicity against HL 60 P 58. Compounds 5f , 5c , 5e and 5b showed potent cytotoxicity against Hela B 75. Antioxidant activity was assessed using three methods, namely, 1,1-diphenyl-2-picrylhydrazyl (DPPH), hydroxyl radical scavenging and ferric reducing antioxidant power (FRAP). The result shows that all these compounds possess significant antioxidant activity. Compounds 5k , 5s , 5a and 5c showed promising antibacterial activity. Compounds 5k , 5u and 5f could be considered as chemopreventive agents.