3-[2-(5-chloro-2-benzyloxy-phenyl)-5-chloro-pyrrol-1-yl]-benzoic acid ethyl ester | 854195-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-[2-(5-chloro-2-benzyloxy-phenyl)-5-chloro-pyrrol-1-yl]-benzoic acid ethyl ester
• 英文别名: Ethyl 3-[2-chloro-5-(5-chloro-2-phenylmethoxyphenyl)pyrrol-1-yl]benzoate
• CAS: 854195-51-0
• 化学式: C₂₆H₂₁Cl₂NO₃
• 分子量: 466.364
• InChiKey: KVAAYUOKJKSIGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[2-(5-chloro-2-benzyloxy-phenyl)-5-chloro-pyrrol-1-yl]-benzoic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.03h， 以100%的产率得到3-[2-Chloro-5-(5-chloro-2-phenylmethoxyphenyl)pyrrol-1-yl]benzoic acid
  参考文献：
  名称：

  Structure–activity relationships of 1,5-biaryl pyrroles as EP1 receptor antagonists

  摘要：

  The preliminary SAR of a series of novel 1,5-biaryl pyrrole EP1 receptor antagonists derived from compound 1 is described. Replacement of the benzyl group of 1 with isosteric groups was investigated. The most effective replacement was found to be the isobutyl group. The cyclopentylmethyl and cyclohexylmethyl groups were also effective benzyl replacements. The cyclohexylmethyl derivative 19 demonstrated the lowest metabolic clearance within this series. In addition, several high affinity substituted benzyl analogues were also identified. Compound 39 was found to have good bioavailability in rats and demonstrated efficacy in the established FCA preclinical model of inflammatory pain with a calculated ED50 of 9.2 mg/kg. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.073
• 作为产物：
  描述：

  3-氨基苯甲酸乙酯 在 N-氯代丁二酰亚胺 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 0.17h， 生成 3-[2-(5-chloro-2-benzyloxy-phenyl)-5-chloro-pyrrol-1-yl]-benzoic acid ethyl ester
  参考文献：
  名称：

  Structure–activity relationships of 1,5-biaryl pyrroles as EP1 receptor antagonists

  摘要：

  The preliminary SAR of a series of novel 1,5-biaryl pyrrole EP1 receptor antagonists derived from compound 1 is described. Replacement of the benzyl group of 1 with isosteric groups was investigated. The most effective replacement was found to be the isobutyl group. The cyclopentylmethyl and cyclohexylmethyl groups were also effective benzyl replacements. The cyclohexylmethyl derivative 19 demonstrated the lowest metabolic clearance within this series. In addition, several high affinity substituted benzyl analogues were also identified. Compound 39 was found to have good bioavailability in rats and demonstrated efficacy in the established FCA preclinical model of inflammatory pain with a calculated ED50 of 9.2 mg/kg. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.073

文献信息

• [EN] PYRROLE COMPOUNDS<br/>[FR] COMPOSES PYRROLE
  申请人：GLAXO GROUP LTD

  公开号：WO2005054191A1

  公开（公告）日：2005-06-16

  Compounds of formula (I) or a derivative thereof: wherein A, B, Z, R1, R2a, R2b, Rx, R8, and R9 are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  式(I)的化合物或其衍生物：其中A、B、Z、R1、R2a、R2b、Rx、R8和R9如规范中定义，制备这种化合物的方法，包含这种化合物的药物组合物以及这种化合物在医学上的用途。
• Pyrrole compounds
  申请人：Giblin Martin Paul Gerard

  公开号：US20070072906A1

  公开（公告）日：2007-03-29

  Compounds of formula (I) or a derivative thereof: wherein A, B, Z, R 1 , R 2a , R 2b , R x , R 6 , and R 9 are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  公式（I）或其衍生物的化合物：其中A，B，Z，R1，R2a，R2b，Rx，R6和R9如规范中所定义，制备这种化合物的过程，包含这种化合物的制药组合物以及这种化合物在医学中的应用。
• PYRROLE COMPOUNDS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1697319A1

  公开（公告）日：2006-09-06
• Structure–activity relationships of 1,5-biaryl pyrroles as EP1 receptor antagonists
  作者：Adrian Hall、Stephen Atkinson、Susan H. Brown、Iain P. Chessell、Anita Chowdhury、Nicholas M. Clayton、Tanya Coleman、Gerard M.P. Giblin、Robert J. Gleave、Beverley Hammond、Mark P. Healy、Matthew R. Johnson、Anton D. Michel、Alan Naylor、Riccardo Novelli、David J. Spalding、Sac P. Tang

  DOI：10.1016/j.bmcl.2006.04.073

  日期：2006.7

  The preliminary SAR of a series of novel 1,5-biaryl pyrrole EP1 receptor antagonists derived from compound 1 is described. Replacement of the benzyl group of 1 with isosteric groups was investigated. The most effective replacement was found to be the isobutyl group. The cyclopentylmethyl and cyclohexylmethyl groups were also effective benzyl replacements. The cyclohexylmethyl derivative 19 demonstrated the lowest metabolic clearance within this series. In addition, several high affinity substituted benzyl analogues were also identified. Compound 39 was found to have good bioavailability in rats and demonstrated efficacy in the established FCA preclinical model of inflammatory pain with a calculated ED50 of 9.2 mg/kg. (c) 2006 Elsevier Ltd. All rights reserved.