高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (3): 531.doi: 10.7503/cjcu20130659

• 有机化学 • 上一篇    下一篇

新型咪唑[2,1-b][1,3,4]噻二唑衍生物的合成及生物活性

李英俊1(), 李春燕1, 靳焜2, 邵昕1, 周晓霞1, 李丽娜1, 赵楠1, 于洋1, 罗潼川1   

  1. 1. 辽宁师范大学化学化工学院, 大连 116029
    2. 大连理工大学精细化工国家重点实验室, 大连 116012
  • 收稿日期:2013-07-15 出版日期:2014-03-10 发布日期:2013-09-13
  • 作者简介:联系人简介: 李英俊, 女, 教授, 主要从事有机合成研究. E-mail: chemlab.lnnu@163.com
  • 基金资助:
    辽宁省自然科学基金(批准号: 20102126)资助

Synthesis and Biological Activity of Novel Imidazo[2,1-b][1,3,4]thiadiazole Derivatives

LI Yingjun1,*(), LI Chunyan1, JIN Kun2, SHAO Xin1, ZHOU Xiaoxia1, LI Lina1, ZHAO Nan1, YU Yang1, LUO Tongchuan1   

  1. 1. College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China
    2. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, China
  • Received:2013-07-15 Online:2014-03-10 Published:2013-09-13
  • Contact: LI Yingjun E-mail:chemlab.lnnu@163.com
  • Supported by:
    † Supported by the Natural Science Foundation of Liaoning Province, China(No.20102126)

摘要:

合成了18个新型含苯并噁/噻唑啉酮结构的2,6-二取代咪唑[2,1-b][1,3,4]噻二唑衍生物5a~5i', 即2-[(2-苯并噁/噻唑啉酮-3-基)甲基]-6-芳基-咪唑[2,1-b][1,3,4]噻二唑. 利用红外光谱、 核磁共振和元素分析对化合物的结构进行了表征. β2-肾上腺素受体(β2-AR)拮抗剂钙流筛选结果表明, 部分目标化合物对β2-AR具有明显的拮抗作用, 其中化合物5c'的拮抗效果最高, 为70%. 这些化合物可作为潜在的β2-AR拮抗剂.

关键词: 2-苯并噁/噻唑啉酮, 咪唑[2,1-b][1,3,4]噻二唑, β2-AR拮抗剂

Abstract:

To develop new β2-AR antagonists, eighteen novel 2,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives containing 2-benzoxazolinone/benzothiazolinone moiety, 2-[(2-benzoxazolinone/benzothiazolinone-3-yl)methyl]-6-aryl-imidazo[2,1-b][1,3,4]thiadiazoles(5a—5i'), were synthesized by the condensation of compounds 4a and 4a' with α-bromoarylketones under reflux in dry ethanol. Their structures of the newly synthesized compounds were confirmed by IR, 1H NMR and elemental analysis. The target compounds were screened as β2-adrenergic receptor antagonist. The result indicated that some of them display obvious antagonistic effects to β2-AR, and compound 5c' shows the highest antagonistic effect(70%). They can be considered as potential candidates as novel β2-AR antagonists.

Key words: 2-Benzoxazolinone/Benzothiazolinone, Imidazo[2,1-b][1,3,4]thiadiazole, β2-Adrenergic receptor antagonist

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