Chemoselective synthesis and cytotoxic activity of a series of novel benzo[1,4]oxazin-3-one derivatives  

作　　者：Peng Wang Fei Liu Qiu Zhong Shi-Long Zheng Yue Chen Guang-Di Wang Ling He 

机构地区：[1]Key Laboratory of Drug-Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Siehuan University, Chengdu 610041, China [2]RCMI Cancer Research Center, Xavier University of Louisiana, New Orleans 70125, USA [3]Department of Chemistry, Xavier University of Louisiana, New Orleans 70125, USA [4]Department of Nuclear Medicine Affiliated Hospital, Luzhou Medical College, Luzhou 646000, China

出　　处：《Chinese Chemical Letters》2017年第6期1243-1247,共5页中国化学快报（英文版）

基　　金：financially supported by the National Natural Science Foundation of China(No.21072131);Sichuan University--Lu Zhou Strategic Cooperation Projects(No.2013CDLZ-S18)(LingHe);the NIH RCMI program at Xavier University of Louisiana(No.2G12MD007595-07)(G.Wang)

摘　　要：That tetraacetonitrile copper perchlorate catalyzes intramolecular amidation of arenes was found to be a new strategy for construction of nitrogen-containing heterocycles and resulted in the formation of a series of novel benzo[1,4]oxazin-3-one derivatives from N-（1,3-diphenyl-1H-1,2,4-triazol-5-yl）-2-phenoxyacetamides.This approach of heterocyclic construction proceeds in a chemoselective manner in which only benzo[1,4]oxazin-3-one derivatives were obtained by C—N bonds formation with cheap and simple copper salt catalyst under mild conditions in moderate to good yields.The biological assay of some of benzo[1,4]oxazin-3-one derivatives showed that they had moderate antiproliferative activity toward MDA-MB231 and HeLa cancer cell lines.That tetraacetonitrile copper perchlorate catalyzes intramolecular amidation of arenes was found to be a new strategy for construction of nitrogen-containing heterocycles and resulted in the formation of a series of novel benzo[1,4]oxazin-3-one derivatives from N-（1,3-diphenyl-1H-1,2,4-triazol-5-yl）-2-phenoxyacetamides.This approach of heterocyclic construction proceeds in a chemoselective manner in which only benzo[1,4]oxazin-3-one derivatives were obtained by C—N bonds formation with cheap and simple copper salt catalyst under mild conditions in moderate to good yields.The biological assay of some of benzo[1,4]oxazin-3-one derivatives showed that they had moderate antiproliferative activity toward MDA-MB231 and HeLa cancer cell lines.

关 键 词：Intramolecular amination Copper catalysis Benzoxazinones Triazol-3-amid Antiproliferative activity 

分 类 号：O621.251[理学—有机化学]