1-[[5-bromo-2-[(4-chlorophenyl)methoxy]phenyl]methyl]-4-piperidinone | 851547-40-5

• 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: 1-[[5-bromo-2-[(4-chlorophenyl)methoxy]phenyl]methyl]-4-piperidinone
• 英文别名: 1-[[5-Bromo-2-[(4-chlorophenyl)methoxy]phenyl]methyl]piperidin-4-one
• CAS: 851547-40-5
• 化学式: C₁₉H₁₉BrClNO₂
• 分子量: 408.722
• InChiKey: IRHTWLKWBXJAQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  514.0±45.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[[5-bromo-2-[(4-chlorophenyl)methoxy]phenyl]methyl]-4-piperidinone 在 ammonium hydroxide 、 potassium tert-butylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 4-(aminomethyl)-1-[[5-bromo-2-[(4-chlorophenyl)methoxy]phenyl]methyl]-4-piperidinol
  参考文献：
  名称：

  CCR5 receptor antagonists: Discovery and SAR of novel 4-hydroxypiperidine derivatives

  摘要：

  The guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde, 1, with an IC50 of 840 nM against the CCR5 receptor was identified using high-throughput screening. Optimization efforts led to the discovery of a novel piperidine series of CCR5 antagonists. In particular, the 4-hydroxypiperidine derivative, 6k, had improved potency against CCR5, and was a starting point for further optimization. SAR elaboration using parallel synthesis led to the identification of 10h, a potent CCR5 antagonist with an IC50 of 11 nM. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.050
• 作为产物：
  描述：

  5-溴-2-[(4-氯苄基)氧基]苯甲醛 在 sodium tetrahydroborate 、 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[[5-bromo-2-[(4-chlorophenyl)methoxy]phenyl]methyl]-4-piperidinone
  参考文献：
  名称：

  CCR5 receptor antagonists: Discovery and SAR of novel 4-hydroxypiperidine derivatives

  摘要：

  The guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde, 1, with an IC50 of 840 nM against the CCR5 receptor was identified using high-throughput screening. Optimization efforts led to the discovery of a novel piperidine series of CCR5 antagonists. In particular, the 4-hydroxypiperidine derivative, 6k, had improved potency against CCR5, and was a starting point for further optimization. SAR elaboration using parallel synthesis led to the identification of 10h, a potent CCR5 antagonist with an IC50 of 11 nM. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.050

文献信息

• Benzylether amine compounds useful as CCR-5 antagonists
  申请人：Davey David

  公开号：US20050101644A1

  公开（公告）日：2005-05-12

  The present invention relates to compounds which are CCR-5 receptor antagonists of the general formula I: wherein R 1 , R 2 , R 3 , R 4 , R a , R b , R c , R d , X, m and n are as defined herein. The invention further comprises pharmaeceutical compositions comprising such compounds, as well as the use of such compounds to treat CCR-5 mediated disorders.

  本发明涉及一般式I的CCR-5受体拮抗剂化合物，其中R1、R2、R3、R4、Ra、Rb、Rc、Rd、X、m和n的定义如本文所述。该发明还包括包含这些化合物的药物组合物，以及利用这些化合物治疗CCR-5介导的疾病的用途。
• BENZYLETHER AMINE COMPOUNDS USEFUL AS CCR-5 ANTAGONISTS
  申请人：Schering Aktiengesellschaft

  公开号：EP1687268A1

  公开（公告）日：2006-08-09
• [EN] BENZYLETHER AMINE COMPOUNDS USEFUL AS CCR-5 ANTAGONISTS<br/>[FR] COMPOSES DE BENZYLAMINE UTILES EN TANT QU'ANTAGONISTES DES CCR-5
  申请人：SCHERING AG

  公开号：WO2005047249A1

  公开（公告）日：2005-05-26

  The present invention relates to compounds which are CCR-5 receptor antagonists of the general formula (I) wherein R1, R2, R3, R4, Ra, Rb, Rc, Rd, X, m and n are as defined herein. The invention further comprises pharmaceutical compositions comprising such compounds, as well as the use of such compounds to treat CCR-5 mediated disorders.