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1.
Scheme 1

Scheme 1. Synthetic Routes Facilitating Diversification of Pyridone Scaffold. From: Pyridones as Highly Selective, Noncovalent Inhibitors of T790M Double Mutants of EGFR.

Reagents and conditions: (a) 2-methyl-2-butene, NaClO2, NaPO4H2–H2O; (b) HBTU or oxalyl or thionyl chloride, NH2R1; (c) HCl; (d) NHR2R3, Δ; (e) R1C1NH2C2NH2, MeOH, Δ.

Marian C. Bryan, et al. ACS Med Chem Lett. 2016 Jan 14;7(1):100-104.

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2.
Figure 1

Figure 1. From: Pyridones as Highly Selective, Noncovalent Inhibitors of T790M Double Mutants of EGFR.

(A) Crystal structure of the apo-TMLR double mutant (PDB 5EDP). The pocket surface is shown in gray. Compound 2 is overlaid. (B) X-ray structure of compound 2 with the TMLR double mutant. Hinge residues Met793 and Gln791 are shown. The pocket surface is shown in gray. (C) Overlay of compound 2 (cyan) with the erlotinib crystal structure with wtEGFR (orange) showing the pocket created by Thr790 (gray surface) (PDB 1M17). (D) Structure of erlotinib with biochemical potency in wtEGFR and TMLR.

Marian C. Bryan, et al. ACS Med Chem Lett. 2016 Jan 14;7(1):100-104.

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