ethyl 4-(4-((2,4-dichlorobenzyl)amino)piperidin-1-yl)-2-(pyridin-4-yl)thiazole-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-(4-((2,4-dichlorobenzyl)amino)piperidin-1-yl)-2-(pyridin-4-yl)thiazole-5-carboxylate
• 化学式: C₂₃H₂₄Cl₂N₄O₂S
• 分子量: 491.441
• InChiKey: FFGQQHNVACOLOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  67.35
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  硫代异烟酰胺 在 吡啶 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 28.0h， 生成 ethyl 4-(4-((2,4-dichlorobenzyl)amino)piperidin-1-yl)-2-(pyridin-4-yl)thiazole-5-carboxylate
  参考文献：
  名称：

  Thiazole–aminopiperidine hybrid analogues: Design and synthesis of novel Mycobacterium tuberculosis GyrB inhibitors

  摘要：

  A series of ethyl-4-(4-((substituted benzyl)amino)piperidin-1-yl)-2-(phenyl/pyridyl)thiazole-5-carboxy lates was designed by molecular hybridization and synthesized from aryl thioamides in five steps. The compounds were evaluated for their in vitro Mycobacterium smegmatis (MS) GyrB ATPase assay, Mycobacterium tuberculosis (MTB) DNA gyrase super coiling assay, antituberculosis activity and cytotoxicity. Among the twenty four compounds studied, ethyl-4-(44(4-fluorobenzypamino)piperidin-1-y1)-2-phenylthiazole-5-carboxylate (14) was found to be the promising compound which showed activity against all test with MS GyrB IC50 of 24.0 +/- 2.1 mu M, 79% inhibition of MTB DNA gyrase at 50 tM, MTB MIC of 28.44 mu M, and not cytotoxic at 50 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.025

文献信息

• Thiazole–aminopiperidine hybrid analogues: Design and synthesis of novel Mycobacterium tuberculosis GyrB inhibitors
  作者：Variam Ullas Jeankumar、Janupally Renuka、Peddi Santosh、Vijay Soni、Jonnalagadda Padma Sridevi、Priyanka Suryadevara、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2013.09.025

  日期：2013.12

  A series of ethyl-4-(4-((substituted benzyl)amino)piperidin-1-yl)-2-(phenyl/pyridyl)thiazole-5-carboxy lates was designed by molecular hybridization and synthesized from aryl thioamides in five steps. The compounds were evaluated for their in vitro Mycobacterium smegmatis (MS) GyrB ATPase assay, Mycobacterium tuberculosis (MTB) DNA gyrase super coiling assay, antituberculosis activity and cytotoxicity. Among the twenty four compounds studied, ethyl-4-(44(4-fluorobenzypamino)piperidin-1-y1)-2-phenylthiazole-5-carboxylate (14) was found to be the promising compound which showed activity against all test with MS GyrB IC50 of 24.0 +/- 2.1 mu M, 79% inhibition of MTB DNA gyrase at 50 tM, MTB MIC of 28.44 mu M, and not cytotoxic at 50 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.