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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 2: 414 - 418

DOI: https://doi.org/10.6023/cjoc201307028

Notes

Synthesis of 2,4-Diaminoquinazoline and 2,4-Diaminopyrido- [2,3-d]pyrimidine Derivatives

  • Deng Lanqing ,
  • Zhong Hong ,
  • Wang Shuai
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  • a College of Chemistry and Chemical Engineering, Central South University, Changsha 410083;
    b Key Laboratory of Yueyang Chinese Herbal Utilization, Yueyang Vocational Technical College, Yueyang 414000;
    c Key Laboratory of Resourse Chemistry of Nonferrous Metals, Ministry of Education Central South University, Changsha 410083

Received date: 2013-07-18

  Revised date: 2013-10-09

  Online published: 2013-10-16

Supported by

Project supported by the National High Technology Research and Development Program of China (863 Program, No. 2013AA064102) and the Project of Science and Technology of Hunan Province (No. 2010FJ4112).

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Abstract

In this work, several 2,4-diaminoquinazoline and 2,4-diaminopyrido[2,3-d]pyrimidine derivatives were designed and synthesized by acylation reaction and ring-closure reaction, using 6-chloro-5-cyanonicotinic acid, 3-cyano-4-fluoroben- zoic acid, 4-cyano-3-fluorobenzoic acid and 6-chloro-5-cyanopicolinic acid as starting materials. This method is simple and efficient. For the used acids but 6-chloro-5-cyanopicolinic acid, the reaction yields are above 65%. The structures of terminational compounds were determined by 1H NMR, 13C NMR and LC-MS. The antitumor activities of the nitrogen mustard-linked chalcones were evaluated by an MTT assay. The results reveal that some of the title compounds exhibit potent anti-proliferative activities against selected tumor cells. Among which, compounds 4c, 4d, 4e and 4f against K562 and HepG2 were better than 5-fluorouracil.

Key words： 2,4-diaminoquinazoline; 2,4-diaminopyrido[2,3-d]pyrimidine; acylation reaction; synthesis

Cite this article

Deng Lanqing , Zhong Hong , Wang Shuai . Synthesis of 2,4-Diaminoquinazoline and 2,4-Diaminopyrido- [2,3-d]pyrimidine Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(2) : 414 -418 . DOI: 10.6023/cjoc201307028

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