cis-4-nitro-benzoic acid 4-amino-cyclohexyl ester | 948303-89-7

• 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: cis-4-nitro-benzoic acid 4-amino-cyclohexyl ester
• 英文别名: cis-4-nitrobenzoic acid 4-aminocyclohexyl ester
• CAS: 948303-89-7
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: COIOIHFAPCRFNU-KLPPZKSPSA-N

物化性质

• 沸点：
  421.5±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  95.46
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  cis-4-nitro-benzoic acid 4-amino-cyclohexyl ester 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 cis-1-(4-chloro-3-trifluoromethylphenyl)-3-(4-hydroxycyclohexyl)urea
  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
• 作为产物：
  描述：

  2-(cis-4-hydroxycyclohexyl)isoindoline-1,3-dione 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 cis-4-nitro-benzoic acid 4-amino-cyclohexyl ester
  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

文献信息

• SORAFENIB DERIVATIVES AS SEH INHIBITORS
  申请人：Hammock Bruce D.

  公开号：US20140088156A1

  公开（公告）日：2014-03-27

  The present invention provides compounds for the inhibition of soluble epoxide hydrolase and associated disease conditions.

  本发明提供了用于抑制可溶性环氧酰胺酶及相关疾病状况的化合物。
• Synthesis and biological evaluation of sorafenib- and regorafenib-like sEH inhibitors
  作者：Sung Hee Hwang、Aaron T. Wecksler、Guodong Zhang、Christophe Morisseau、Long V. Nguyen、Samuel H. Fu、Bruce D. Hammock

  DOI：10.1016/j.bmcl.2013.05.011

  日期：2013.7

  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.
• Orally Bioavailable Potent Soluble Epoxide Hydrolase Inhibitors
  作者：Sung Hee Hwang、Hsing-Ju Tsai、Jun-Yan Liu、Christophe Morisseau、Bruce D. Hammock

  DOI：10.1021/jm070270t

  日期：2007.8.1

  A series of N,N'-disubstituted ureas having a conformationally restricted cis- or traiis-1,4-cyclohexane alpha to the urea were prepared and tested as soluble epoxide hydrolase (sEH) inhibitors. This series of compounds showed low nanomolar to picomolar activities against recombinant human sEH. Both isomers showed similar potencies, but the trans isomers were more metabolically stable in human hepatic microsomes. Furthermore, these new potent inhibitors show a greater metabolic stability in vivo than previously described sEH inhibitors. We demonstrated that trans-4-[4-(3-adamantan-1-ylureido)cyclohexyloxy]benzoic acid 13g (t-AUCB, IC50 = 1.3 +/- 0.05 nM) had excellent oral bioavailability (98%, n = 2) and blood area under the curve in dogs and was effective in vivo to treat hypotension in lipopolysaccharide challenged murine models.
• SORAFENIB DERIVATIVES AS sEH INHIBITORS
  申请人：The Regents of the University of California

  公开号：EP2675274B1

  公开（公告）日：2017-05-03
• US9029401B2
  申请人：——

  公开号：US9029401B2

  公开（公告）日：2015-05-12