4-(3-cyanophenyl)-4-hydroxycyclohexan-1-one | 887950-87-0

• 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: 4-(3-cyanophenyl)-4-hydroxycyclohexan-1-one
• 英文别名: 3-(1-hydroxy-4-oxo-cyclohexyl)-benzonitrile；3-(1-Hydroxy-4-oxocyclohexyl)benzonitrile
• CAS: 887950-87-0
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: MRCGMTLLNDKWCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-cyanophenyl)-4-hydroxycyclohexan-1-one 在 三乙基硅烷 、 sodium cyanoborohydride 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-[4-(3-Cyano-phenyl)-cyclohex-3-enyl]-3-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-urea
  参考文献：
  名称：

  Bicyclic[4.1.0]heptanes as phenyl replacements for melanin concentrating hormone receptor antagonists

  摘要：

  Melanin concentrating hormone (MCH) receptor antagonists have been proposed as potential treatments of obesity. MCH receptor antagonists with a biphenylamine subunit have been reported previously at Schering-Plough. Herein, we report the discovery of bicyclo[4.1.0]heptanes as replacements for the middle phenyl ring of the biphenylamine moiety, in order to eliminate its potential mutagenic liability. Structure-activity relationships in this series were found to be very similar to those of the original biphenylamine series, suggesting that the two series have similar binding modes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.046
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 正丁基锂 、 对甲苯磺酸 、 丙酮 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.17h， 生成 4-(3-cyanophenyl)-4-hydroxycyclohexan-1-one
  参考文献：
  名称：

  Bicyclic[4.1.0]heptanes as phenyl replacements for melanin concentrating hormone receptor antagonists

  摘要：

  Melanin concentrating hormone (MCH) receptor antagonists have been proposed as potential treatments of obesity. MCH receptor antagonists with a biphenylamine subunit have been reported previously at Schering-Plough. Herein, we report the discovery of bicyclo[4.1.0]heptanes as replacements for the middle phenyl ring of the biphenylamine moiety, in order to eliminate its potential mutagenic liability. Structure-activity relationships in this series were found to be very similar to those of the original biphenylamine series, suggesting that the two series have similar binding modes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.046

文献信息

• 4-AZETIDINYL-1-PHENYL-CYCLOHEXANE ANTAGONISTS OF CCR2
  申请人：Zhang Xuqing

  公开号：US20100267689A1

  公开（公告）日：2010-10-21

  The present invention comprises compounds of Formula (I): wherein: X, R 1 , R 2 , R 3 , and R 4 are as defined in the specification. The invention also comprises a method of preventing, treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is type II diabetes, obesity and asthma. The invention also comprises a method of inhibiting CCR2 activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula (I).

  本发明涵盖了以下式（I）的化合物： 其中：X，R1，R2，R3和R4如规范中所定义。该发明还涵盖了一种预防、治疗或改善综合征、疾病或疾病的方法，其中所述综合征、疾病或疾病是II型糖尿病、肥胖和哮喘。该发明还涵盖了通过给哺乳动物施用至少一种式（I）化合物的治疗有效量来抑制CCR2活性的方法。
• Overcoming hERG activity in the discovery of a series of 4-azetidinyl-1-aryl-cyclohexanes as CCR2 antagonists
  作者：Xuqing Zhang、Heather Hufnagel、Thomas Markotan、James Lanter、Chaozhong Cai、Cuifen Hou、Monica Singer、Evan Opas、Sandra McKenney、Carl Crysler、Dana Johnson、Zhihua Sui

  DOI：10.1016/j.bmcl.2011.06.080

  日期：2011.9

  A series of 4-azetidinyl-1-aryl-cyclohexanes as potent CCR2 antagonists with high selectivity over activity for the hERG potassium channel is discovered through divergent SARs of CCR2 and hERG. (C) 2011 Elsevier Ltd. All rights reserved.
• US8513229B2
  申请人：——

  公开号：US8513229B2

  公开（公告）日：2013-08-20
• [EN] 4-AZETIDINYL-1-PHENYL-CYCLOHEXANE ANTAGONISTS OF CCR2<br/>[FR] ANTAGONISTES DE CCR2 A BASE DE 4-AZETIDINYL-1-PHENYL-CYCLOHEXANE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2010121046A1

  公开（公告）日：2010-10-21

  The present invention comprises compounds of Formula (I) wherein: X, R1, R2, R3, and R4 are as defined in the specification. The invention also comprises a method of preventing, treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is type II diabetes, obesity and asthma. The invention also comprises a method of inhibiting CCR2 activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula (I).