高等学校化学学报Issue(3)：555-563,9.DOI:10.7503/cjcu20130543
含1,2,4-三唑环的亚胺及酰亚胺类化合物的合成及生物活性
Syntheses and Biological Activities of Novel Imine and Imide Derivatives Bearing 1,2,4-Triazole Moiety
摘要
Abstract
According to active groups combination principle, a series of novel imine and imide derivatives bearing 1,2,4-triazole moiety was designed and synthesized. The key intermediate 3-substituted phenyl-4-ami-no-1,2,4-triazole-5-thiones was synthesized by esterification, hydrazinolysis, salt and cyclization reactions, and then was condensed with aromatic aldehydes and isobenzofuran-1 , 3-dione to obtain imine and imide derivatives, which were subjected to the thioetherification with suitable halides ( RX ) to produce the corre-sponding 24 novel imine and imide derivatives bearing 1,2,4-triazole moiety. The structures of target com-pounds were fully characterized by 1 H NMR, IR, mass spectroscopy and elemental analysis. The preliminary bioassay results showed that most of the compounds possessed certain fungicidal activities. At the concentration of 150 mg/L, the inhibition rates of compounds 9a, 9d and 9e against Rhizoctonia solani were very similar with the commercial fungicide Flusilazole. Meanwhile, the preliminary structure-activity relationships( SAR) were discussed in order to investigate the essential structures required for their bioactivities. In addition, their in vitro antitumor activities were evaluated against three cancer cell lines [ human alveolar epithelial cells ( A549 ) , human breast cancer cells ( MD-MBA-231 ) and human prostate cancer cells ( PC-3 M ) ] by the methyl thiazolyl tetrazolium(MTT) chromatometry method with Fluorouracil as a positive contrast drug. The bioassay data indicated that compounds 7c, 7f and 9k showed similar antiproliferation with Fluorouracil against A549 cell lines with IC50 values of 38.3, 44.6 and 36.7μmol/L, respectively. Most interestingly, compound 9k also exhibited a broad spectrum of antitumor activity against MCF-7 and MKN45 with IC50 values of 147.5 and 60.7 μmol/L, respectively.关键词
1 ,2 ,4-三唑/杀菌活性/抗肿瘤活性Key words
1 ,2 ,4-Triazole/Fungicidal activity/Antitumor activity分类
化学化工引用本文复制引用
杨海葵,许万福,段安娜,游文玮,赵培亮..含1,2,4-三唑环的亚胺及酰亚胺类化合物的合成及生物活性[J].高等学校化学学报,2014,(3):555-563,9.基金项目
国家自然科学基金(批准号:21372113)、高等学校博士学科点专项科研基金(批准号:20104433120011)和广州市珠江科技新星专项资助项目(批准号:2012J2200051)资助.@@@@ Supported by the National Natural Science Foundation of China(No.21372113), the Specialized Research Fund for the Doctoral Program of Higher Education( New Teachers), China( No.20104433120011), and the Project of Science and Technology New Star in Zhujiang Guangzhou City, China(No.2012J2200051) （批准号:21372113）
