5-bromo-2-[(4-chlorophenyl)methoxy]-N,N-dimethylbenzenemethanamine | 851546-88-8

• 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: 5-bromo-2-[(4-chlorophenyl)methoxy]-N,N-dimethylbenzenemethanamine
• 英文别名: 1-[5-bromo-2-[(4-chlorophenyl)methoxy]phenyl]-N,N-dimethyl-methanamine；1-[5-bromo-2-[(4-chlorophenyl)methoxy]phenyl]-N,N-dimethylmethanamine
• CAS: 851546-88-8
• 化学式: C₁₆H₁₇BrClNO
• 分子量: 354.674
• InChiKey: GNJMHFOKSMUCQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-[(4-chlorophenyl)methoxy]-N,N-dimethylbenzenemethanamine 、 碘甲烷 在 甲苯 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 5-bromo-2-[(4-chlorophenyl)methoxy]-N,N,N-trimethyl-benzenemethanammonium iodide
  参考文献：
  名称：

  Benzylether amine compounds useful as CCR-5 antagonists

  摘要：

  本发明涉及一种通式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。本发明还包括包含这些化合物的药物组成物，以及使用这些化合物治疗CCR-5介导的疾病的方法。

  公开号：

  US20050101644A1
• 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 5-bromo-2-[(4-chlorophenyl)methoxy]-N,N-dimethylbenzenemethanamine
  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

• CCR5 receptor antagonists: Discovery and SAR study of guanylhydrazone derivatives
  作者：Robert G. Wei、Damian O. Arnaiz、Yuo-Ling Chou、Dave Davey、Laura Dunning、Wheeseong Lee、Shou-Fu Lu、James Onuffer、Bin Ye、Gary Phillips

  DOI：10.1016/j.bmcl.2006.09.052

  日期：2007.1

  High throughput screening (HTS) led to the identification of the guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde as a CCR5 receptor antagonist. Initial modifications of the guanylhydrazone series indicated that substitution of the benzyl group at the para-position was well tolerated. Substitution at the 5-position of the central phenyl ring was critical for potency. Replacement of the guanylhydrazone group led to the discovery of a novel series of CCR5 antagonists. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.