VER-24052 | 1186316-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: VER-24052
• 英文别名: {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}piperidin-1-ylmethanone；(3-[(4-chlorophenyl)-(2-chloropyrid-3-yl)methoxy]azetidin-1-yl)piperidin-1-ylmethanone；[3-[(4-Chlorophenyl)-(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]-piperidin-1-ylmethanone
• CAS: 1186316-76-6
• 化学式: C₂₁H₂₃Cl₂N₃O₂
• 分子量: 420.339
• InChiKey: QEKKZTBXSULKCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  VER-24052 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 40.0h， 以80%的产率得到3-[(4-chlorophenyl)({1-[(piperidin-1-yl)carbonyl]azetidin-3-yl}oxy)methyl]-1,2-dihydropyridin-2-one
  参考文献：
  名称：

  Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity

  摘要：

  We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.032
• 作为产物：
  描述：

  4-氯苯基溴化镁 在 吡啶 、 sodium tetrahydroborate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 33.45h， 生成 VER-24052
  参考文献：
  名称：

  Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity

  摘要：

  We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.032

文献信息

• Fatty acid amide hydrolase inhibitors. Surprising selectivity of chiral azetidine ureas
  作者：Terance Hart、Alba T. Macias、Karen Benwell、Teresa Brooks、Jalanie D’Alessandro、Pawel Dokurno、Geraint Francis、Ben Gibbons、Timothy Haymes、Guy Kennett、Sean Lightowler、Howard Mansell、Natalia Matassova、Anil Misra、Anthony Padfield、Rachel Parsons、Robert Pratt、Alan Robertson、Steven Walls、Melanie Wong、Stephen Roughley

  DOI：10.1016/j.bmcl.2009.05.097

  日期：2009.8

  We report the discovery of a novel, chiral azetidine urea inhibitor of Fatty Acid Amide Hydrolase ( FAAH,) and describe the surprising species selectivity of VER-156084 versus rat and human FAAH and also hCB1. (C) 2009 Elsevier Ltd. All rights reserved.
• Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity
  作者：Stephen D. Roughley、Helen Browne、Alba T. Macias、Karen Benwell、Teresa Brooks、Jalanie D’Alessandro、Zoe Daniels、Sarah Dugdale、Geraint Francis、Ben Gibbons、Terance Hart、Timothy Haymes、Guy Kennett、Sean Lightowler、Natalia Matassova、Howard Mansell、Angela Merrett、Anil Misra、Anthony Padfield、Rachel Parsons、Robert Pratt、Alan Robertson、Heather Simmonite、Kiri Tan、Steven B. Walls、Melanie Wong

  DOI：10.1016/j.bmcl.2011.12.032

  日期：2012.1

  We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats. (C) 2011 Elsevier Ltd. All rights reserved.