1-[(4-carboxyphenyl)methyl]-3-(2-mercaptoethyl)-1H-indole-2-carboxylic acid | 560131-47-7

• 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-[(4-carboxyphenyl)methyl]-3-(2-mercaptoethyl)-1H-indole-2-carboxylic acid
• 英文别名: 1-[(4-carboxyphenyl)methyl]-3-(2-sulfanylethyl)indole-2-carboxylic acid
• CAS: 560131-47-7
• 化学式: C₁₉H₁₇NO₄S
• 分子量: 355.414
• InChiKey: DHGLLNLERWLFEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  80.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1-[(4-carboxyphenyl)methyl]-3-(2-mercaptoethyl)-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

• Indoles as naaladase inhibitors
  申请人：Tsukamoto Takashi

  公开号：US20050080128A1

  公开（公告）日：2005-04-14

  This invention relates to new compounds, pharmaceutical compositions and diagnostic kits comprising such compounds, and methods of using such compounds for inhibiting NAALADase enzyme activity, detecting diseases where NAALAdase levels are altered, effecting neuronal activity, effecting TGF-β activity, inhibiting angiogenesis, and treating glutamate abnormalities, neuropathy, pain, compulsive disorders, prostate diseases, cancers and glaucoma.

  本发明涉及新化合物、制药组合物和诊断试剂盒，包括这些化合物，并且使用这些化合物的方法用于抑制NAALADase酶活性、检测NAALAdase水平发生变化的疾病、影响神经元活动、影响TGF-β活性、抑制血管生成以及治疗谷氨酸异常、神经病、疼痛、强迫性障碍、前列腺疾病、癌症和青光眼。
• US7148250B2
  申请人：——

  公开号：US7148250B2

  公开（公告）日：2006-12-12
• [EN] INDOLES AS NAALADASE INHIBITORS<br/>[FR] INDOLES EN TANT QU'INHIBITEURS DE L'ENZYME NAALADASE
  申请人：GUILFORD PHARM INC

  公开号：WO2003057670A2

  公开（公告）日：2003-07-17

  This invention relates to new compounds, pharmaceutical compositions and diagnostic kits comprising such compounds, and methods of using such compounds for inhibiting NAALADase enzyme activity, detecting diseases where NAALAdase levels are altered, effecting neuronal activity, effecting TGF-β activity, inhibiting angiogenesis, and treating glutamate abnormalities, neuropathy, pain, compulsive disorders, prostate diseases, cancers and glaucoma.
• 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.