Synthesis of Novel Quinazolin-4-one Derivatives Bearing Benzo[c]-chromen-6-one and Their Anti-tumor and Antimicrobial Activities

doi:10.6023/cjoc201608024

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (2): 429-439.DOI: 10.6023/cjoc201608024 Previous Articles Next Articles

ARTICLE

含苯并香豆素的喹唑啉-4-酮衍生物的合成及其抗肿瘤、抗菌活性

冯钰欣, 谭官海, 周利凯, 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:2016-08-25 修回日期:2016-09-13 发布日期:2016-10-11
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.2015201005）资助项目.

Synthesis of Novel Quinazolin-4-one Derivatives Bearing Benzo[c]-chromen-6-one and Their Anti-tumor and Antimicrobial Activities

Feng Yuxin, Tan Guanhai, Zhou Likai, 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:2016-08-25 Revised:2016-09-13 Published:2016-10-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372060), the Natural Science Fund for Distinguished Young Scholars (Incubation) of Hebei Province (No. B2015201005).

1. Synthesis of Novel Quinazolin-4-one Derivatives Bearing Benzo[c]-chromen-6-one and Their Anti-tumor and Antimicrobial Activities.PDF(719KB)

Abstract

A series of novel quinazolin-4(3H)-one derivatives 3a~3e and 4a possessing 3,4-benzo[c]coumarin and amino side chain were designed and synthesized by the condensation reaction of 2-aminobenzamide and 3,4-benzo[c] coumarin aldehyde prepared by Heck coupling reaction, followed by S_N2 substitution reaction with haloalkane. The compounds were evaluated for their anti proliferation activities against four tumor cells and antimicrobial activities. The results showed that 3e showed moderate anti Hela activity with the IC₅₀ value of 22.63 and 23.35 μmol/L for 4a against MCF-7. Most tested compounds exhibited significant anti Escherichia coli activities, and the inhibition rate was above 89% at the concentration of 50 μg/mL. The inhibition rates of 2-phenyl-4-(2-(piperidin-1-yl)ethoxy)quinazoline (1b) against Fusarium oxysporum and Rhizoctonia solani and 3d against Verticillium dahliae are 100%.

Key words: quinazolin-4-one, 3,4-benzo[c]coumarin, Heck coupling reaction, anti-tumor activity, antimicrobial activity

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Feng Yuxin, Tan Guanhai, Zhou Likai, Wang Shuxia, Chen Hua, Li Xiaoliu. Synthesis of Novel Quinazolin-4-one Derivatives Bearing Benzo[c]-chromen-6-one and Their Anti-tumor and Antimicrobial Activities[J]. Chin. J. Org. Chem., 2017, 37(2): 429-439.

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含苯并香豆素的喹唑啉-4-酮衍生物的合成及其抗肿瘤、抗菌活性

Synthesis of Novel Quinazolin-4-one Derivatives Bearing Benzo[c]-chromen-6-one and Their Anti-tumor and Antimicrobial Activities

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