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

doi:10.6023/cjoc201307028

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (2): 414-418.DOI: 10.6023/cjoc201307028 Previous Articles Next Articles

Notes

2,4-二氨基喹唑啉和2,4-二氨基吡啶并[2,3-d]嘧啶衍生物的合成

邓兰青^a,b, 钟宏^a,c, 王帅^a,c

a 中南大学化学化工学院长沙 410083;
b 岳阳职业技术学院岳阳市中草药综合利用重点实验室岳阳 414000;
c 有色金属资源化学教育部重点实验室中南大学长沙 410083

收稿日期:2013-07-18 修回日期:2013-10-09 发布日期:2013-10-16
通讯作者: 钟宏 E-mail:zhongh@csu.edu.cn
基金资助:
国家高技术研究发展计划（863计划，No.2013AA064102）和湖南省科技厅（No.2010FJ4112）资助项目.

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

Deng Lanqing^a,b, Zhong Hong^a,c, Wang Shuai^a,c

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:2013-07-18 Revised:2013-10-09 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).

1. Synthesis of 2,4-Diaminoquinazoline and 2,4-Diaminopyrido- [2,3-d]pyrimidine Derivatives.PDF(1045KB)

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]. Chin. J. Org. Chem., 2014, 34(2): 414-418.

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2,4-二氨基喹唑啉和2,4-二氨基吡啶并[2,3-d]嘧啶衍生物的合成

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

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