4-(4-(6-chloro-1-(cyclohexylmethyl)-1H-benzo[d]imidazol-2-yl)phenyl)morpholine | 1365392-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-(4-(6-chloro-1-(cyclohexylmethyl)-1H-benzo[d]imidazol-2-yl)phenyl)morpholine
• 英文别名: 4-[4-[6-Chloro-1-(cyclohexylmethyl)benzimidazol-2-yl]phenyl]morpholine
• CAS: 1365392-69-3
• 化学式: C₂₄H₂₈ClN₃O
• 分子量: 409.959
• InChiKey: NJRFDPRELYWIJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-硝基-5-氯苯胺 在 sodium dithionite 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙醇 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 4-(4-(6-chloro-1-(cyclohexylmethyl)-1H-benzo[d]imidazol-2-yl)phenyl)morpholine
  参考文献：
  名称：

  SAR-study on a new class of imidazo[1,2-a]pyridine-based inhibitors of 5-lipoxygenase

  摘要：

  A novel class of 5-lipoxygenase (5-LO) inhibitors characterized by a central imidazo[1,2-a] pyridine scaffold, a cyclohexyl moiety and an aromatic system, is presented. This scaffold was identified in a virtual screening study and exhibits promising inhibitory potential on the 5-LO. Here, we investigate the structure-activity relationships of this compound class. With N-cyclohexyl-6-methyl-2-(4-morpholinophenyl)imidazo[1,2-a]pyridine-3-amine (14), we identified a potent 5-LO inhibitor (IC50 = 0.16 mu M (intact cells) and 0.1 mu M (cell-free)), which may possess potential as an effective lead compound intervening with inflammatory diseases and certain types of cancer. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.038

文献信息

• SAR-study on a new class of imidazo[1,2-a]pyridine-based inhibitors of 5-lipoxygenase
  作者：Martina Hieke、Carmen B. Rödl、Joanna M. Wisniewska、Estel. la Buscató、Holger Stark、Manfred Schubert-Zsilavecz、Dieter Steinhilber、Bettina Hofmann、Ewgenij Proschak

  DOI：10.1016/j.bmcl.2012.01.038

  日期：2012.3

  A novel class of 5-lipoxygenase (5-LO) inhibitors characterized by a central imidazo[1,2-a] pyridine scaffold, a cyclohexyl moiety and an aromatic system, is presented. This scaffold was identified in a virtual screening study and exhibits promising inhibitory potential on the 5-LO. Here, we investigate the structure-activity relationships of this compound class. With N-cyclohexyl-6-methyl-2-(4-morpholinophenyl)imidazo[1,2-a]pyridine-3-amine (14), we identified a potent 5-LO inhibitor (IC50 = 0.16 mu M (intact cells) and 0.1 mu M (cell-free)), which may possess potential as an effective lead compound intervening with inflammatory diseases and certain types of cancer. (C) 2012 Elsevier Ltd. All rights reserved.