1-(3-carboxybenzyl)-3-(carboxymethyl)-1H-indole-2-carboxylic acid | 1261639-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(3-carboxybenzyl)-3-(carboxymethyl)-1H-indole-2-carboxylic acid
• 英文别名: 3-(carboxymethyl)-1-[(3-carboxyphenyl)methyl]indole-2-carboxylic acid
• CAS: 1261639-09-1
• 化学式: C₁₉H₁₅NO₆
• 分子量: 353.331
• InChiKey: CWUWJMHHVJSCEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 3-(2-methoxy-2-oxoethyl)-1-(3-(methoxycarbonyl)benzyl)-1H-indole-2-carboxylate 在 甲醇 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到1-(3-carboxybenzyl)-3-(carboxymethyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  The discovery and structure–activity relationships of indole-based inhibitors of glutamate carboxypeptidase II

  摘要：

  A series of N-substituted 3-(2-mercaptoethyl)-1H-indole-2-carboxylic acids were synthesized as inhibitors of glutamate carboxypeptidase II (GCPII). Those containing carboxybenzyl or carboxyphenyl groups at the N-position exhibited potent inhibitory activity against GCPII. These indole-based compounds represent the first example of achiral GCPII inhibitors and demonstrate greater tolerance of the GCPII active site for ligands with significant structural difference from the endogenous substrate, N-acetyl-aspartylglutamate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.109

文献信息

• The discovery and structure–activity relationships of indole-based inhibitors of glutamate carboxypeptidase II
  作者：Brian Grella、Jessica Adams、James F. Berry、Greg Delahanty、Dana V. Ferraris、Pavel Majer、Chiyou Ni、Krupa Shukla、Scott A. Shuler、Barbara S. Slusher、Marigo Stathis、Takashi Tsukamoto

  DOI：10.1016/j.bmcl.2010.10.109

  日期：2010.12

  A series of N-substituted 3-(2-mercaptoethyl)-1H-indole-2-carboxylic acids were synthesized as inhibitors of glutamate carboxypeptidase II (GCPII). Those containing carboxybenzyl or carboxyphenyl groups at the N-position exhibited potent inhibitory activity against GCPII. These indole-based compounds represent the first example of achiral GCPII inhibitors and demonstrate greater tolerance of the GCPII active site for ligands with significant structural difference from the endogenous substrate, N-acetyl-aspartylglutamate. (C) 2010 Elsevier Ltd. All rights reserved.