2,2,2-trifluoroacetic acid compound with 4-(((1s,4s)-4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)cyclohexyl)oxy)picolinic acid (1:1) | 1394012-04-4

• 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: 2,2,2-trifluoroacetic acid compound with 4-(((1s,4s)-4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)cyclohexyl)oxy)picolinic acid (1:1)
• CAS: 1394012-04-4
• 化学式: C₂HF₃O₂*C₂₀H₁₉ClF₃N₃O₄
• 分子量: 571.861
• InChiKey: POQHGPZSBOUUKL-SPDVTRLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  38.0
• 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：
  137.85
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoroacetic acid compound with 4-(((1s,4s)-4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)cyclohexyl)oxy)picolinic acid (1:1) 、 盐酸二甲胺 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以67%的产率得到cis-4-{4-[3-(4-chloro-3-trifluoromethylphenyl)ureido]cyclohexyloxy}pyridine-2-carboxylic acid methylamide
  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
• 作为产物：
  描述：

  cis-1-(4-chloro-3-trifluoromethylphenyl)-3-(4-hydroxycyclohexyl)urea 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2,2,2-trifluoroacetic acid compound with 4-(((1s,4s)-4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)cyclohexyl)oxy)picolinic acid (1:1)
  参考文献：
  名称：

  [EN] SORAFENIB DERIVATIVES AS sEH INHIBITORS
  [FR] DÉRIVÉS DE SORAFÉNIB UTILISÉS EN TANT QU'INHIBITEURS DE LA SEH

  摘要：

  本发明提供了用于抑制可溶性环氧化物水解酶及相关疾病状况的化合物。

  公开号：

  WO2012112570A1