Design and synthesis of tetrahydropyridothieno[2,3-d]pyrimidine scaffold based epidermal growth factor receptor (EGFR) kinase inhibitors: the role of side chain chirality and Michael acceptor group for maximal potency.

doi:10.1021/jm100607r

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Article

Design and synthesis of tetrahydropyridothieno[2,3-d]pyrimidine scaffold based epidermal growth factor receptor (EGFR) kinase inhibitors: the role of side chain chirality and Michael acceptor group for maximal potency.

Journal of medicinal chemistry - 28 Oct 2010

Wu Chia-Hsien, Coumar Mohane Selvaraj, Chu Chang-Ying, Lin Wen-Hsing, Chen Yi-Rong, Chen Chiung-Tong, Shiao Hui-Yi, Rafi Shaik, Wang Sing-Yi, Hsu Hui, Chen Chun-Hwa, Chang Chun-Yu, Chang Teng-Yuan, Lien Tzu-Wen, Fang Ming-Yu, Yeh Kai-Chia, Chen Ching-Ping, Yeh Teng-Kuang, Hsieh Su-Huei, Hsu John T-A, Liao Chun-Chen, Chao Yu-Sheng, Hsieh Hsing-Pang

Abstract excerpt

HTS hit 7 was modified through hybrid design strategy to introduce a chiral side chain followed by introduction of Michael acceptor group to obtain potent EGFR kinase inhibitors 11 and 19. Both 11 and 19 showed over 3 orders of magnitude enhanced HCC827 antiproliferative activity compared to HTS hit 7 and also inhibited gefitinib-resistant double mutant (DM, T790M/L858R) EGFR kinase at nanomolar concentration....

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PMID: 20961149
DOI: 10.1021/jm100607r

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EGFR

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