摘要
以取代邻硝基苯甲酸为起始原料,与二氯亚砜反应制得邻硝基苯甲酰氯,再与苯胺在碱性条件下反应制得酰胺衍生物(6a^6d);以醋酸钯为催化剂,6a^6d经NBS溴代制得溴代衍生物(7a^7d);7a^7d依次经N-烷基化反应,还原反应和分子内C—N键环合反应合成了10个新型的1,4-二苯并二氮杂酮类化合物(10a^10j),产率61%~78%,其结构经~1H NMR,13C NMR和HR-MS(ESI)表征。初步体外活性测试结果表明:10a^10j对非小细胞肺癌细胞(A549),人乳腺癌细胞(MDA-MB-231)和宫颈癌细胞(He La)均有抑制作用。其中,10g和10i对A549,10g对MDA-MB-231,10h和10i对He La的抑制率大于50%。
The amide derivatives（6a ～ 6d） were obtained by the reaction of substituted o-nitrobenzoic acids with SOCl2, then reaction with aniline under basic condition. The brominated derivatives（7a ～ 7d） were prepared by NBS-bromination of 6a ～ 61t, using Pd（OAc） 2 as the catalyst. Ten novel 1,4- dibenzodiazepin compounds （10a ～ 10j ） were synthesized by the reaction of N-alkylation, reduction and intramolecular C--N bond cyclization from 7a ～ 7d, respectively. The structures were characterized by ^1H NMR, ^13C NMR and HR-MS （ESI）. The preliminary in vitro bio-activity tests showed that 10a ～ 10j had certain inhibitory effects on non-small cell lung cancer cell（ A549 ）, human breast cancer cell（ MDA-MB-231 ） and cervical cancer cell（HeLa）. Among them, the inhibition rates of 10g and 10i on A549, 10g and 10h on MDA-MB-231 and 10i on HeLa were above 50%.
出处
《合成化学》
CAS
CSCD
2017年第8期637-641,共5页
Chinese Journal of Synthetic Chemistry
基金
川大-泸州战略合作基金资助项目(2013CDLZ-S18)
