2-(4-hydroxy-1H-indole-3-carboxamido)acetic acid

• 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: 2-(4-hydroxy-1H-indole-3-carboxamido)acetic acid
• 英文别名: 2-[(4-hydroxy-1H-indole-3-carbonyl)amino]acetic acid
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: UVXQRSXJRVLVPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二甲基溴苄 、 2-(4-hydroxy-1H-indole-3-carboxamido)acetic acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以20%的产率得到2-[1-(3,5-dimethylbenzyl)-4-hydroxy-1H-indole-3-carboxamido]acetic acid
  参考文献：
  名称：

  Fragment hopping approach directed at design of HIV IN-LEDGF/p75 interaction inhibitors

  摘要：

  We recently identified a series of indole derivatives as active inhibitors of IN-LEDGF/p75 interaction through structure-based pharmacophore models generated from the crystal structure of dimeric catalytic core domain (CCD) of HIV-1 IN in complex with the LEDGF integrase binding domain (IBD). In this paper we used the fragment hopping approach to design small molecules able to prevent the IN-LEDGF/p75 interaction. By means of the proposed approach, we designed novel non-peptidyl compounds that mimic the biological function of some IBD residues and in particular the LEDGF hot spot residues Ile365 and Asp366. The biological results confirmed the importance of several structural requirements for the inhibitory effects of this class of compounds.

  DOI：

  10.3109/14756366.2012.703184
• 作为产物：
  描述：

  2-(4-methoxy-1H-indole-3-carboxamido)acetic acid 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到2-(4-hydroxy-1H-indole-3-carboxamido)acetic acid
  参考文献：
  名称：

  Fragment hopping approach directed at design of HIV IN-LEDGF/p75 interaction inhibitors

  摘要：

  We recently identified a series of indole derivatives as active inhibitors of IN-LEDGF/p75 interaction through structure-based pharmacophore models generated from the crystal structure of dimeric catalytic core domain (CCD) of HIV-1 IN in complex with the LEDGF integrase binding domain (IBD). In this paper we used the fragment hopping approach to design small molecules able to prevent the IN-LEDGF/p75 interaction. By means of the proposed approach, we designed novel non-peptidyl compounds that mimic the biological function of some IBD residues and in particular the LEDGF hot spot residues Ile365 and Asp366. The biological results confirmed the importance of several structural requirements for the inhibitory effects of this class of compounds.

  DOI：

  10.3109/14756366.2012.703184

文献信息

• Fragment hopping approach directed at design of HIV IN-LEDGF/p75 interaction inhibitors
  作者：Laura De Luca、Stefania Ferro、Francesca Morreale、Frauke Christ、Zeger Debyser、Alba Chimirri、Rosaria Gitto

  DOI：10.3109/14756366.2012.703184

  日期：2013.10.1

  We recently identified a series of indole derivatives as active inhibitors of IN-LEDGF/p75 interaction through structure-based pharmacophore models generated from the crystal structure of dimeric catalytic core domain (CCD) of HIV-1 IN in complex with the LEDGF integrase binding domain (IBD). In this paper we used the fragment hopping approach to design small molecules able to prevent the IN-LEDGF/p75 interaction. By means of the proposed approach, we designed novel non-peptidyl compounds that mimic the biological function of some IBD residues and in particular the LEDGF hot spot residues Ile365 and Asp366. The biological results confirmed the importance of several structural requirements for the inhibitory effects of this class of compounds.