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
收稿日期: 2016-08-25
修回日期: 2016-09-13
网络出版日期: 2016-10-11
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
Received date: 2016-08-25
Revised date: 2016-09-13
Online 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).
利用Heck偶联反应制备了3，4-苯并香豆素醛，继而与邻氨基苯甲酰胺反应，设计合成了连有苯并香豆素并含氨基侧链的喹唑啉-4-酮衍生物3a~3e和4a，并评价了化合物的抗肿瘤细胞增殖活性及抑菌活性.化合物3e和4a具有中等的抗宫颈癌和乳腺癌细胞增殖活性，IC50值分别为22.63和23.35 μmol/L.部分化合物（50 μg/mL）对大肠杆菌具有显著的抑制活性，抑菌率在89%以上.2-苯基-4-[2-（哌啶-1-基）乙氧基]喹唑啉（1b）对尖孢镰刀菌和立枯丝核菌以及3d对大丽轮枝菌真菌的抑制率均为100%.
冯钰欣 , 谭官海 , 周利凯 , 王淑霞 , 陈华 , 李小六 . 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[J]. 有机化学, 2017 , 37(2) : 429 -439 . DOI: 10.6023/cjoc201608024
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 SN2 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%.
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