(I+/-S)-I+/--Amino-3,5-dibromo-4-hydroxybenzeneacetic acid | 1208237-80-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (I+/-S)-I+/--Amino-3,5-dibromo-4-hydroxybenzeneacetic acid
• 英文别名: (2S)-2-amino-2-(3,5-dibromo-4-hydroxyphenyl)acetic acid
• CAS: 1208237-80-2
• 化学式: C₈H₇Br₂NO₃
• 分子量: 324.956
• InChiKey: SQMNVQXCSHRTOP-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-(+)-对羟基苯甘氨酸 在 溴 、 溶剂黄146 作用下， 反应 4.0h， 生成 (2s)-2-Amino-2-(3-bromo-4-hydroxyphenyl)acetic acid 、 (I+/-S)-I+/--Amino-3,5-dibromo-4-hydroxybenzeneacetic acid
  参考文献：
  名称：

  Bioisosterism of urea-based GCPII inhibitors: Synthesis and structure–activity relationship studies

  摘要：

  We report a strategy based on bioisosterism to improve the physicochemical properties of existing hydrophilic, urea-based GCPII inhibitors. Comprehensive structure-activity relationship studies of the P1' site of ZJ-43- and DCIBzL-based compounds identified several glutamate-free inhibitors with K-i values below 20 nM. Among them, compound 32d (K-i = 11 nM) exhibited selective uptake in GCPII-expressing tumors by SPECT-CT imaging in mice. A novel conformational change of amino acids in the S1' pharmacophore pocket was observed in the X-ray crystal structure of GCPII complexed with 32d. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.061

文献信息

• Bioisosterism of urea-based GCPII inhibitors: Synthesis and structure–activity relationship studies
  作者：Haofan Wang、Youngjoo Byun、Cyril Barinka、Mrudula Pullambhatla、Hyo-eun C. Bhang、James J. Fox、Jacek Lubkowski、Ronnie C. Mease、Martin G. Pomper

  DOI：10.1016/j.bmcl.2009.10.061

  日期：2010.1

  We report a strategy based on bioisosterism to improve the physicochemical properties of existing hydrophilic, urea-based GCPII inhibitors. Comprehensive structure-activity relationship studies of the P1' site of ZJ-43- and DCIBzL-based compounds identified several glutamate-free inhibitors with K-i values below 20 nM. Among them, compound 32d (K-i = 11 nM) exhibited selective uptake in GCPII-expressing tumors by SPECT-CT imaging in mice. A novel conformational change of amino acids in the S1' pharmacophore pocket was observed in the X-ray crystal structure of GCPII complexed with 32d. (C) 2009 Elsevier Ltd. All rights reserved.