文章摘要
杨金来,王石发.异长叶烷基-喹唑啉-2-胺衍生物的合成与生物活性评价[J].精细化工,2019,36(2):0
异长叶烷基-喹唑啉-2-胺衍生物的合成与生物活性评价
Synthesis and Biological Evaluation of Isolongifolanyl-quinazolin-2-amine Derivatives
投稿时间:2018-01-11  修订日期:2018-08-28
DOI:
中文关键词: 异长叶烷酮  喹唑啉-2-胺衍生物  抗肿瘤活性  杀虫活性  医药原料
英文关键词: isolongifolanone  quinazolin-2-amine derivative  antitumor activity  insecticidal activity  drug materials
基金项目:国家自然科学基金(No. 31470592)
作者单位E-mail
杨金来 国家林业局竹子研究开发中心 5491936@163.com 
王石发 南京林业大学 wangshifa65@126.com 
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中文摘要:
      以异长叶烷酮为原料,经缩合,环化等反应合成出6个喹唑啉-2-胺衍生物(Ⅲa~Ⅲf)。采用1HNMR、13CNMR、IR、HRMS等对其结构进行了表征。采用MTT法考察了化合物Ⅲ a~Ⅲf对人肝癌细胞(HepG2)和人脐静脉内皮细胞(HUVECs)的抑制活性。结果表明,化合物Ⅲa、Ⅲb、Ⅲd、Ⅲf〔半抑制浓度(IC50)分别为8.58±0.5、44.52±0.9、57.18±0.8、32.83±0.6 μmol/L〕对HepG2有一定的抗肿瘤活性。其中,4-(4'-氯苯基)-6,6,10,10-四甲基-5,6,6a,7,8,9,10,10a-八氢-6a,9-甲基苯并[h]喹唑啉-2-胺(Ⅲa)抗HepG2的活性最强;只有4-[4'–(二甲基氨基)苯基]-6,6,10,10-四甲基-5,6,6a,7,8,9,10,10a-八氢-6a,9-甲基苯并[h]喹唑啉-2-胺(Ⅲf)对HUVECs有抑制活性。同时,采用叶浸渍法考察了化合物Ⅲa~Ⅲf对桃蚜的杀虫活性,结果表明,化合物Ⅲa、Ⅲd 〔致死中浓度(LC50)=37.4589±6.412, 41.0073±5.920 mg/L〕对桃蚜具有较好的杀虫活性。
英文摘要:
      A series of quinazolin-2-amine derivatives (Ⅲa~Ⅲf) were synthesized by condensation, cyclization and so on from isolongifolanone and characterized by 1HNMR, 13C NMR, IR and HRMS. Their inhibitory activity against human hepatoma cell (HepG2) and human umbilical vein endothelial cells (HUVECs) were evaluated by MTT assay. The results showed that the half maximal inhibitory concentrations of compounds Ⅲa, Ⅲb, Ⅲd and Ⅲf were 8.58±0.5, 44.52±0.9, 57.18±0.8 and 32.83±0.6 μmol/L, indicating that these compounds showed moderate antitumor activity against HepG2. Among these compounds, compound Ⅲa, 4-(4'-chlorophenyl)-6,6,10,10-tetramethyl-5,6,6a,7,8,9,10,10a-octahydro-6a,9-methanobenzo[h]quinazolin-2-amine, had the best activity against HepG2. Only 4-(4'-(N,N-dimethylamino)phenyl)-6,6,10,10-tetramethyl-5,6,6a,7,8,9,10,10a-octahydro-6a,9-methanobenzo[h]quinazolin-2-amine (Ⅲf) showed a certain inhibitory activity against HUVECs. These compounds were also carried out to evaluate against myzus persicae by a leaf-dipping method. It was found that compounds Ⅲa and Ⅲd gave excellent insecticidal activity against myzus persicae with corresponding lethal concentration (LC50) of 37.4589±6.412 and 41.0073±5.920 mg/L.
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