trans-3-{4-[3-(4-chloro-3-trifluoromethylphenyl)ureido]cyclohexyloxy}-N-methylbenzamide | 1443543-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-3-{4-[3-(4-chloro-3-trifluoromethylphenyl)ureido]cyclohexyloxy}-N-methylbenzamide
• CAS: 1443543-98-3
• 化学式: C₂₂H₂₃ClF₃N₃O₃
• 分子量: 469.891
• InChiKey: TXYLJBZWPCKJLZ-KOMQPUFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  79.46
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  trans-4-aminocyclohexanol hydrochloride 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium hydride 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 30.0h， 生成 trans-3-{4-[3-(4-chloro-3-trifluoromethylphenyl)ureido]cyclohexyloxy}-N-methylbenzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of sorafenib- and regorafenib-like sEH inhibitors

  摘要：

  To reduce the pro-angiogenic effects of sEH inhibition, a structure-activity relationship (SAR) study was performed by incorporating structural features of the anti-angiogenic multi-kinase inhibitor sorafenib into soluble epoxide hydrolase (sEH) inhibitors. The structural modifications of this series of molecules enabled the altering of selectivity towards the pro-angiogenic kinases C-RAF and vascular endothelial growth factor receptor-2 (VEGFR-2), while retaining their sEH inhibition. As a result, sEH inhibitors with greater potency against C-RAF and VEGFR-2 were obtained. Compound 4 (t-CUPM) possesses inhibition potency higher than sorafenib towards sEH but similar against C-RAF and VEGFR-2. Compound 7 (t-CUCB) selectively inhibits sEH, while inhibiting HUVEC cell proliferation, a potential anti-angiogenic property, without liver cancer cell cytotoxicity. The data presented suggest a potential rational approach to control the angiogenic responses stemming from sEH inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.011