Synthesis and Anti-tumor Activity of Novel Quinazolin-4-one Derivatives

doi:10.6023/cjoc201607045

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (2): 455-461.DOI: 10.6023/cjoc201607045 Previous Articles Next Articles

ARTICLE

喹唑啉-4-酮衍生物的合成及抗肿瘤活性

孙佳婧, 周利凯, 谭官海, 李帅, 王淑霞, 陈华, 李小六

河北大学化学与环境科学学院河北省化学生物学重点实验室保定 071002

收稿日期:2016-07-29 修回日期:2016-09-13 发布日期:2016-10-09
通讯作者: 陈华, 李小六 E-mail:lixl@hbu.cn;hua-todd@163.com
基金资助:
国家自然科学基金（No.21372060）、河北省自然科学杰出青年基金（培育）（No.B2015201005）资助项目.

Synthesis and Anti-tumor Activity of Novel Quinazolin-4-one Derivatives

Sun Jiajing, Zhou Likai, Tan Guanhai, Li Shuai, Wang Shuxia, Chen Hua, Li Xiaoliu

Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002

Received:2016-07-29 Revised:2016-09-13 Published:2016-10-09
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372060), the Hebei Provincal Natural Science Fund for Distinguished Young Scholars (Incubation) (No. B2015201005).

1. Synthesis and Anti-tumor Activity of Novel Quinazolin-4-one Derivatives.PDF(375KB)

Abstract

A series of novel C-2 and N-3 disubstituted quinazolin-4(3H)-one derivatives 5 possessing amino acid chain were synthesized by the addition reaction of imine with iminoketene and aromatization using anthranilic acid, aromatic aldehyde and glycine ethyl ester as starting materials. After elimination of carboxymethyl in the acidic condition, novel quinazolin-4(3H)-one derivatives 9 bearing amino side chain were designed and synthesized by SN2 substitution reaction. The compounds were evaluated for their anti-proliferation activities against four tumor cells. The results showed that some of the compounds, such as 9ba and 9bc showed significantly anti Hela activity with the IC₅₀ values of 8.16 μM and 7.47 μM, respectively, while 9bc and 9bd against A549 with the IC₅₀ values of 5.62 μM and 9.54 μM, respectively. Structure activity relationship analysis of these analogues suggested that coumarin substituent (extended π planar aromatic ring) on C-2 position and the introduction of amino side chain should be favorable to their anti-tumor activities.

Key words: quinazolin-4-one, anti-tumor activity, iminoketene, amino side chain, elimination of carboxymethyl, coumarin

Cite this article

Sun Jiajing, Zhou Likai, Tan Guanhai, Li Shuai, Wang Shuxia, Chen Hua, Li Xiaoliu. Synthesis and Anti-tumor Activity of Novel Quinazolin-4-one Derivatives[J]. Chin. J. Org. Chem., 2017, 37(2): 455-461.

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喹唑啉-4-酮衍生物的合成及抗肿瘤活性

Synthesis and Anti-tumor Activity of Novel Quinazolin-4-one Derivatives

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