Epigallocatechin-3-gallate (EGCG) is the main and most investigated catechin in green tea. Despite good in vivo activity against HT-29 xenografts tumor growth, the clinical application of EGCG has been hindered due to its poor bioavailability and stability associated with the gallyl moiety and galloyl moiety. In an attempt to improve the stability while keeping the anticancer activity, a total of seven EGCG analogs have been synthesized in 10 steps. The galloyl ring was replaced with rings capable of forming hydrogen bond interactions such as quinoline, 4-methoxy phenyl, pyridine etc… The gallyl ring was replaced by a 4-hydroxy phenyl ring to avoid the instability problem and the two hydroxyl groups in ring A were converted into methoxy groups. The antiproliferative potential of the compounds was evaluated using HTC-116 cells. The compound with the best activity was (2R,3R)-2-(4-hydroxyphenyl)-5,7-dumethoxychroman-3yl benzoate with LD50= 8.5µM.

Design and synthesis of EGCG analogs for the treatment of colon cancer

ACS Fall 2020 Virtual Meeting

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