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Design, Synthesis and Cytotoxic Evaluation of o-Carboxamido Stilbene Analogues
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
Department of Chemistry, Faculty of Science and Mathematics, Sultan Azlan Shah Campus, University Pendidikan Sultan Idris, Proton City 35950, Perak Darul Ridzuan, Malaysia
Department of Pharmacy, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur 50603, Malaysia
* Author to whom correspondence should be addressed.
Received: 15 July 2013; in revised form: 13 September 2013 / Accepted: 17 September 2013 / Published: 27 November 2013
Abstract: Resveratrol, a natural stilbene found in grapes and wines exhibits a wide range of pharmacological properties. Resveratrol is also known as a good chemopreventive agent for inhibiting carcinogenesis processes that target kinases, cyclooxygenases, ribonucleotide reductase and DNA polymerases. A total of 19 analogues with an amide moiety were synthesized and the cytotoxic effects of the analogues on a series of human cancer cell lines are reported. Three compounds 6d, 6i and 6n showed potent cytotoxicity against prostate cancer DU-145 (IC50 = 16.68 µM), colon cancer HT-29 (IC50 = 7.51 µM) and breast cancer MCF-7 (IC50 = 21.24 µM), respectively, which are comparable with vinblastine. The resveratrol analogues were synthesized using the Heck method.
Keywords: o-carboxamido stilbenes; amido stilbenes; Heck protocol; cytotoxic effects
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Azmi, M.N.; Din, M.F.M.; Kee, C.H.; Suhaimi, M.; Ping, A.K.; Ahmad, K.; Nafiah, M.A.; Thomas, N.F.; Mohamad, K.; Hoong, L.K.; Awang, K. Design, Synthesis and Cytotoxic Evaluation of o-Carboxamido Stilbene Analogues. Int. J. Mol. Sci. 2013, 14, 23369-23389.
Azmi MN, Din MFM, Kee CH, Suhaimi M, Ping AK, Ahmad K, Nafiah MA, Thomas NF, Mohamad K, Hoong LK, Awang K. Design, Synthesis and Cytotoxic Evaluation of o-Carboxamido Stilbene Analogues. International Journal of Molecular Sciences. 2013; 14(12):23369-23389.
Azmi, Mohamad N.; Din, Mohd F.M.; Kee, Chin H.; Suhaimi, Munirah; Ping, Ang K.; Ahmad, Kartini; Nafiah, Mohd A.; Thomas, Noel F.; Mohamad, Khalit; Hoong, Leong K.; Awang, Khalijah. 2013. "Design, Synthesis and Cytotoxic Evaluation of o-Carboxamido Stilbene Analogues." Int. J. Mol. Sci. 14, no. 12: 23369-23389.