4-(2-(2-(4-(pyrrolidin-1-yl)benzylidene)hydrazinyl)thiazol-4-yl)benzonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-(2-(2-(4-(pyrrolidin-1-yl)benzylidene)hydrazinyl)thiazol-4-yl)benzonitrile
• 化学式: C₂₁H₁₉N₅S
• 分子量: 373.481
• InChiKey: UTNXIUBCFYAUBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  64.31
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-(1-吡咯啉基)苯甲醛 以 乙醇 为溶剂， 反应 7.0h， 生成 4-(2-(2-(4-(pyrrolidin-1-yl)benzylidene)hydrazinyl)thiazol-4-yl)benzonitrile
  参考文献：
  名称：

  Design, synthesis and biological assessment of new thiazolylhydrazine derivatives as selective and reversible h MAO-A inhibitors

  摘要：

  In the recent works, it was shown that numerous thiazolylhydrazine derivatives display hMAO inhibitory activity in the range of micromolar concentration. Hence, in the present study a new series of new thiazole-hydrazines (3a-3n) were designed, synthesized, characterized and screened for their hMAO-A and hMAO-B inhibitory activity by an in vitro flurometric method. The enzyme inhibition assay revealed that most of the synthesized compounds have selective inhibition potency against hMAO-A. The compounds 3f and 3h showed promising hMAO-A inhibition with an IC50 values of 0.012 mu M and 0.011 mu M and significant selectivity indexes of 1214 and 1601 towards hMAO-A, respectively. The mechanism of hMAO-A inhibition of compounds 3f and 3h was investigated by Lineweaver-Burk graphics and reversible-competitive inhibition of hMAO-A was determined. Cytotoxicity and genotoxicity studies were carried out and the compound 3h was found as non-cytotoxic and non-genotoxic. Theoretical calculation of ADME properties suggested that synthesized compounds may have a good pharmacokinetic profile. The docking study of compound 3f and 3h revealed that there is a strong interaction between the active sites of hMAO-A and analyzed compound. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.013