The synthesis of 4-arylamido-2-arylaminoprimidines as potent EGFR T790M/L858R inhibitors for NSCLC

Bioorganic & Medicinal Chemistry
2018.0

Abstract

A series of 4-arylamido-2-arylaminoprimidines bearing acrylamide pharmacophore were synthesized as potent EGFR<sup>T790M/L858R</sup> inhibitors among which 9c (IC<sub>50</sub> = 0.5872 nM), 9d (IC<sub>50</sub> = 2.213 nM), or 9h (IC<sub>50</sub> = 12.57 nM) showed more potent anti-EGFR<sup>T790M/L858R</sup> activity compared with AZD-9291 (IC<sub>50</sub> = 20.80 nM) and possessed high SI displaying 307.6, 56.5, or 12.5 for EGFR<sup>T790M/L858R</sup> over the wild-type respectively. 9h also showed pretty good activity against H 1975 cells with an IC<sub>50</sub> of 1.664 μM and exhibited low toxicity against the normal HBE cells (IC<sub>50</sub> > 20 μΜ). 9h had moderate selectivity for H 1975 over A 431 (SI = 7.0) and the other selected cell lines. Morphological staining results further indicated that 9h could promote apoptosis. Hence, 9h was a promising compound for further investigation as a potential EGFR<sup>T790M/L858R</sup> inhibitor for the treatment of NSCLC.

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