Novel 2,4-Diarylaminopyrimidine Derivatives Containing Pyridine Moiety: Design, Synthesis, Crystal Structure and Biological Evaluation

A series of 2,4-diarylaminopyrimidine derivatives containing pyridine structure were designed and synthesized. The crystal structures of compounds 5d and 5e were obtained from X-ray diffraction. The crystal structure of 5d (C25H20ClFN6O2) belongs to the monoclinic system, space group P2(1)/c with a = 11.0500(10), b = 18.3045(17), c = 13.5646(9) angstrom and beta = 122.806(5)degrees. 5e (C25H19ClF2N6O2) is of monoclinic system, space group P2(1)/c with a = 10.9998(18), b = 18.517(3), c = 13.6355(16) angstrom and ) beta = 123.315(9)degrees. The bioassay results showed all of the target compounds exhibited potential antiproliferative activities against MKN-45, HT-29, A549, K562 and GIST882 cell lines. Among them, compounds 5a, 5c and 5e exhibited remarkable inhibitory activities against GIST882, K562 and A549 cell lines with IC50 values of 0.68, 0.38 and 0.60 mu M, respectively, which were comparable to that of the positive control foretinib.

Automated summary

A series of 2,4-diarylaminopyrimidine derivatives with pyridine structure were synthesized and their crystal structures were determined by X-ray diffraction. The bioassay results demonstrated that these compounds exhibited potential antiproliferative activities against various cell lines.