trans-N-[4-(4-hydroxyphenyl)cyclohexyl]-3-phenylpropionamide

• 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-N-[4-(4-hydroxyphenyl)cyclohexyl]-3-phenylpropionamide
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: RLDCTYNUILGEQM-UAPYVXQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 trans-N-[4-(4-hydroxyphenyl)cyclohexyl]-3-phenylpropionamide
  参考文献：
  名称：

  Discovery of novel and orally active NR2B-selective N-methyl-d-aspartate (NMDA) antagonists, pyridinol derivatives with reduced HERG binding affinity

  摘要：

  Novel NR2B antagonists with an amide tether were found by an approach to avoid pharmacophoric similarity to dofetilide. Structure-activity relationship investigation led to N-[cis-4-hydroxy-4-(5-hydroxypyridin-2-yl)cyclohexyl]-3-henylpropanamide 14e as an orally active NR2B-subtype selective N-methyl-D-aspartate (NMDA) receptor antagonist with very weak HERG (human ether-a-go-go related gene) binding (IC50 > 30 mu M). This compound exhibited potent in vivo anti-allodynic activity in the mouse partial sciatic nerve ligation (PSL) model (minimum effective dose = 10 mg/kg, po). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.039

文献信息

• [EN] 2-PYRIDYL AND 2-PYRIMIDYL CYCLOALKYLENE AMIDE COMPOUNDS AS NR2B RECEPTOR ANTAGONISTS<br/>[FR] 2-PYRIDYL-CYCLOALKYLENE-AMIDES ET 2-PYRIMIDYL-CYCLOALKYLENE-AMIDES CONSTITUANT DES ANTAGONISTES DU RECEPTEUR NR2B
  申请人：PFIZER JAPAN INC

  公开号：WO2004054579A1

  公开（公告）日：2004-07-01

  This invention provides a compound of the Formula (I), wherein R1 represents Formula (II), wherein R5 represents a hydroxy group or the like; R6 represents a hydrogen atom or the like. Z represents a carbon or a nitrogen atom: R2 represents a hydrogen atom or the like: R3 represents a hydrogen or the like: A represents a cycloalkylene or the like: X represents a covalent bond or the like: R4 represents an aryl or the like. These compounds are useful for the treatment of disease conditions caused by overactivation of NMDA NR2B receptor such as pain, or the like in mammals. This invention also provides a pharmaceutical composition comprising the above compound.

  本发明提供了一种Formula(I)化合物，其中R1代表Formula(II)，其中R5代表羟基或类似物；R6代表氢原子或类似物。Z代表一个碳原子或氮原子：R2代表氢原子或类似物：R3代表氢原子或类似物：A代表环烷基或类似物：X代表共价键或类似物：R4代表芳基或类似物。这些化合物对于治疗由NMDA NR2B受体过度激活引起的疾病状况如疼痛等在哺乳动物中是有用的。本发明还提供了包含上述化合物的制药组合物。
• Cyclohexylamine derivative as subtype selective nmda receptor antagonists
  申请人：——

  公开号：US20030236286A1

  公开（公告）日：2003-12-25

  Described are compounds of Formula I and Formula II and their pharmaceutically acceptable salts. The compounds of Formulas I and II are antagonists of NMDA receptor channel complexes useful for treating cerebral vascular disorders such as, for example, cerebral ischemia, cardiac arrest, stroke, and Parkinson's disease. 1

  描述了公式I和公式II的化合物及其药学上可接受的盐。公式I和II的化合物是NMDA受体通道复合物的拮抗剂，可用于治疗脑血管疾病，例如脑缺血、心脏停搏、中风和帕金森病。
• TRANS-N-¬4-(4-HYDROXYPHENYL)CYCLOHEXYL|-3-PHENYLPROPIONAMIDE AS SUBTYPE SELECTIVE NMDA RECEPTOR ANTAGONIST
  申请人：Warner-Lambert Company LLC

  公开号：EP1278716B1

  公开（公告）日：2006-08-23
• US6919377B2
  申请人：——

  公开号：US6919377B2

  公开（公告）日：2005-07-19
• Discovery of novel and orally active NR2B-selective N-methyl-d-aspartate (NMDA) antagonists, pyridinol derivatives with reduced HERG binding affinity
  作者：Makoto Kawai、Hiroshi Nakamura、Isao Sakurada、Hirohisa Shimokawa、Hirotaka Tanaka、Miyako Matsumizu、Kazuo Ando、Kazunari Hattori、Atsuko Ohta、Seiji Nukui、Atsushi Omura、Mitsuhiro Kawamura

  DOI：10.1016/j.bmcl.2007.08.039

  日期：2007.10

  Novel NR2B antagonists with an amide tether were found by an approach to avoid pharmacophoric similarity to dofetilide. Structure-activity relationship investigation led to N-[cis-4-hydroxy-4-(5-hydroxypyridin-2-yl)cyclohexyl]-3-henylpropanamide 14e as an orally active NR2B-subtype selective N-methyl-D-aspartate (NMDA) receptor antagonist with very weak HERG (human ether-a-go-go related gene) binding (IC50 > 30 mu M). This compound exhibited potent in vivo anti-allodynic activity in the mouse partial sciatic nerve ligation (PSL) model (minimum effective dose = 10 mg/kg, po). (c) 2007 Elsevier Ltd. All rights reserved.