Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and …

…, K Awang, K Takeya, H Morita, SI Hussain…

Index: Kee, Chin Hui; Ariffin, Azhar; Awang, Khalijah; Takeya, Koichi; Morita, Hiroshi; Hussain, Salmaan Inayat; Chan, Kok Meng; Wood, Pauline J.; Threadgill, Michael D.; Lim, Chuan Gee; Ng, Seikweng; Weber, Jean Frederic F.; Thomas, Noel F. Organic and Biomolecular Chemistry, 2010 , vol. 8, # 24 p. 5646 - 5660

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Citation Number: 5

Abstract

The syntheses of fourteen unusual o-carboxamido stilbenes by the Heck protocol revealed surprising complexity related to intriguing substituent effects with mechanistic implications. The unexpected cytotoxic and chemopreventive properties also seem to be substituent dependent. For example, although stilbene 15d (with a 4-methoxy substituent) showed cytotoxicity on HT29 colon cancer cells with an IC50 of 4.9 μM, the 3, 4-dimethoxy ...