文章摘要
朱芸莹,柏松,吴琴.不对称Mannich反应合成手性含1,3,4-噻二唑的丙二酸酯衍生物[J].精细化工,2019,36(7):
不对称Mannich反应合成手性含1,3,4-噻二唑的丙二酸酯衍生物
Synthesis of Chiral Malonate Derivatives Containing 1,3,4-Thiadiazole Moiety by Asymmetric Mannich Reaction
投稿时间:2019-01-22  修订日期:2019-04-04
DOI:
中文关键词: 丙二酸酯衍生物  不对称Mannich反应  抗病毒活性
英文关键词: chiral malonate derivatives  asymmetric mannich reaction  anti-plant virus activity
基金项目:贵州省教育厅青年科技人才成长项目(黔教合KY字[2018]251);贵州省科技计划项目(黔科合平台人才[2017]5789);贵州大学绿色农药实验室开放基金资助项目(2018GDGP0102);贵州省自然科学基金(黔科合基础[2017]1066);贵州理工学院高层次人才启动基金
作者单位E-mail
朱芸莹 贵州理工学院 yyingzhu@sina.com 
柏松 贵州理工学院 Basonmail@163.com 
吴琴 贵州理工学院 wuqin1974@163.com 
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中文摘要:
      以金鸡纳碱方酰胺为催化剂,采用不对称Mannich反应,催化剂Ⅴe摩尔分数为10%,溶剂为甲苯,温度为60 ℃的最佳反应条件下一锅法合成了9个手性含1,3,4-噻二唑的丙二酸酯衍生物(Ⅳa~i),具有较高的收率(70%~89%)和优异的对映选择性(e.e.值最高>99%)。生物活性测试结果表明:该类衍生物对烟草花叶病毒具有一定的活性,其中手性化合物(-)-Ⅳf的治疗和保护活性分别为50.8%和42.6%,与对照商品化药剂病毒唑相当。
英文摘要:
      Nine chiral malonate derivatives containing 1,3,4-thiadiazole moiety (Ⅳa~i) were synthesized by one-pot asymmetric Mannich reaction using cinchona alkaloid squaramide catalyst. High yields (70%~89%) and excellent enantioselectivities [up to>99%, enantiomeric excess (e.e.)] were obtained in toluene in the presence of 10 mol% catalyst Ⅴe at 60 ℃ which were the optimum reaction conditions . The bioassay results showed that these derivatives possessed good activities against tobacco mosaic virus (TMV). Especially, chiral compound (-)-Ⅳf exhibited high curative and protective activities against TMV in vivo (50.8% and 42.6%, respectively), equivalent to that of commercially available antiviral agent riba-virin.
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