Citation: Ju LIU, Shuang WU, Huan WANG, Si-Yuan DU, Zhen LI, Ji-Wei SHEN, Ye CHEN, Shi DING. Novel 2, 4-Diarylaminopyrimidine Derivatives Containing Pyridine Moiety: Design, Synthesis, Crystal Structure and Biological Evaluation[J]. Chinese Journal of Structural Chemistry, ;2022, 41(2): 220213. doi: 10.14102/j.cnki.0254-5861.2011-3283 shu

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

Ju LIU ^{a, b, c} ,
Shuang WU ^a ,
Huan WANG ^a ,
Si-Yuan DU ^a ,
Zhen LI ^a ,
Ji-Wei SHEN ^{a, b, c} ,
Ye CHEN ^{a, b, c,,} ,
Shi DING ^{a, b, c,,}

a.
College of Pharmacy of Liaoning University, Shenyang 110036, China
b.
API Engineering Technology Research Center of Liaoning Province, Shenyang 110036, China
c.
Small Molecular Targeted Drug R & D Engineering Research Center of Liaoning Province, Shenyang 110036, China

Corresponding author: Ye CHEN, sy-chenye@163.com Shi DING, dingshi_destiny@163.com
Received Date: 10 June 2021
Accepted Date: 10 August 2021

Fund Project: the Youth National Natural Science Foundation of China 21807055the General Project of Education Department of Liaoning Province LJC201907Natural Science Foundation of Liaoning Provincial Department of Science and Technology 2019-ZD-0191the College Students' Innovation and Entrepreneurship Training Program of Liaoning University D202011280014195636

Figures(5)

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 P2₁/c with a = 11.0500(10), b = 18.3045(17), c = 13.5646(9) Å and β = 122.806(5)°. 5e (C₂₅H₁₉ClF₂N₆O₂) is of monoclinic system, space group P2₁/c with a = 10.9998(18), b = 18.517(3), c = 13.6355(16) Å and β = 123.315(9)°. 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 μM, respectively, which were comparable to that of the positive control foretinib.
- pyrimidine,
- pyridine,
- synthesis,
- X-ray diffraction,
- antitumor activity
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