ethyl 2-(4-amino-3-bromophenyl)propionate

• 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: ethyl 2-(4-amino-3-bromophenyl)propionate
• 英文别名: 2-(4-amino-3-bromo-phenyl)-propionic acid ethyl ester；ethyl 2-(4-amino-3-bromophenyl)propanoate
• 化学式: C₁₁H₁₄BrNO₂
• 分子量: 272.142
• InChiKey: LUDYWEGXWKJTMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-amino-3-bromophenyl)propionate 在 吡啶 、 四(三苯基膦)钯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 22.17h， 生成 N-(4-tert-butylbenzyl)-2-[3-methyl-4-(methylsulfonylamino)phenyl]propionamide
  参考文献：
  名称：

  N-4-t-Butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure–activity relationships in the A-region

  摘要：

  Structure-activity relationships for the A-region in a series of N-4-t-butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamides as TRPV1 antagonists have been investigated. Among them, the 3-fluoro analogue 54 showed high binding affinity and potent antagonism for both rTRPV1 and hTRPV1 in CHO cells. Its stereospecific activity was demonstrated with marked selectivity for the (S)-configuration (54S versus 54R). A docking study of 54S with our hTRPV1 homology model highlighted crucial hydrogen bonds between the ligand and the receptor contributing to its potency. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.008
• 作为产物：
  描述：

  2-氯丙酸乙酯 在 potassium tert-butylate 、 铁粉 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.19h， 生成 ethyl 2-(4-amino-3-bromophenyl)propionate
  参考文献：
  名称：

  N-4-t-Butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure–activity relationships in the A-region

  摘要：

  Structure-activity relationships for the A-region in a series of N-4-t-butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamides as TRPV1 antagonists have been investigated. Among them, the 3-fluoro analogue 54 showed high binding affinity and potent antagonism for both rTRPV1 and hTRPV1 in CHO cells. Its stereospecific activity was demonstrated with marked selectivity for the (S)-configuration (54S versus 54R). A docking study of 54S with our hTRPV1 homology model highlighted crucial hydrogen bonds between the ligand and the receptor contributing to its potency. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.008

文献信息

• Vanilloid Receptor Ligands, Pharmaceutical Compositions Containing Them, Process for Making Them, and Use Thereof for Treating Pain and Other Conditions
  申请人：FRANK Robert

  公开号：US20090156590A1

  公开（公告）日：2009-06-18

  Vanilloid receptor ligand compounds corresponding to formula I: pharmaceutical compositions containing such compounds, a process for producing such compounds, and methods of using such compounds for treating or inhibiting pain and various other disorders or conditions.

  与公式I相对应的辣椒素受体配体化合物：含有这种化合物的药物组合物，生产这种化合物的方法，以及使用这种化合物治疗或抑制疼痛和各种其他疾病或症状的方法。
• Vanilloid Receptor Ligands, Pharmaceutical Compositions Containing Them, Process For Making Them, and Use Thereof to Treat Pain and Other Conditions
  申请人：Frank Robert

  公开号：US20110301156A1

  公开（公告）日：2011-12-08

  Vanilloid receptor ligand compounds corresponding to formula I: pharmaceutical compositions containing such compounds, a process for producing such compounds, and methods of using such compounds for treating or inhibiting pain and various other disorders or conditions.

  Vanilloid受体配体化合物I式对应的药物组成物，含有这种化合物的药物组成物，制备这种化合物的过程，以及使用这种化合物治疗或抑制疼痛和各种其他疾病或情况的方法。
• Vanilloid receptor ligands, pharmaceutical compositions containing them, process for making them, and use thereof for treating pain and other conditions
  申请人：Gruenenthal GmbH

  公开号：US08084484B2

  公开（公告）日：2011-12-27

  Vanilloid receptor ligand compounds corresponding to formula I: pharmaceutical compositions containing such compounds, a process for producing such compounds, and methods of using such compounds for treating or inhibiting pain and various other disorders or conditions.

  公式I所对应的vanilloid受体配体化合物：包含这些化合物的药物组合物，制备这些化合物的过程，以及使用这些化合物治疗或抑制疼痛和各种其他疾病或病况的方法。
• Vanilloid receptor ligands, pharmaceutical compositions containing them, process for making them, and use thereof to treat pain and other conditions
  申请人：Frank Robert

  公开号：US08785474B2

  公开（公告）日：2014-07-22

  Vanilloid receptor ligand compounds corresponding to formula I: pharmaceutical compositions containing such compounds, a process for producing such compounds, and methods of using such compounds for treating or inhibiting pain and various other disorders or conditions.

  配方I相应的辣椒素受体配体化合物：含有这种化合物的制药组合物，生产这种化合物的过程，以及使用这种化合物治疗或抑制疼痛和各种其他疾病或症状的方法。
• Discovery of 2-(3,5-difluoro-4-methylsulfonaminophenyl)propanamides as potent TRPV1 antagonists
  作者：Changhoon Kim、Jihyae Ann、Sunho Lee、Wei Sun、Peter M. Blumberg、Robert Frank-Foltyn、Gregor Bahrenberg、Hannelore Stockhausen、Thomas Christoph、Jeewoo Lee

  DOI：10.1016/j.bmcl.2018.05.043

  日期：2018.8

  A series of A-region analogues of 2-(3-fluoro-4-methylsufonamidophenyl)propanamide 1 were investigated as TRPV1 antagonists. The analysis of structure-activity relationship indicated that a fluoro group at the 3-(or/and) 5-position and a methylsulfonamido group at the 4-position were optimal for antagonism of TRPV1 activation by capsaicin. The most potent antagonist 6 not only exhibited potent antagonism of activation of hTRPV1 by capsaicin, low pH and elevated temperature but also displayed highly potent antagonism of activation of rTRPV1 by capsaicin. Further studies demonstrated that antagonist 6 blocked the hypothermic effect of capsaicin in vivo, consistent with its in vitro mechanism, and it showed promising analgesic activity in the formalin animal model.