(R)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)-propionic acid methyl ester | 124986-53-4

• 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: (R)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)-propionic acid methyl ester
• 英文别名: methyl (2R)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoate
• CAS: 124986-53-4
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: QOBUNYVBTXFCEZ-SNVBAGLBSA-N

物化性质

• 沸点：
  453.3±40.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)-propionic acid methyl ester 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 生成 (2R)-2-[[1-cyclohexyl-2-(3-furyl)benzimidazole-5-carbonyl]amino]-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  Non-nucleoside inhibitors of the hepatitis C virus NS5B polymerase: discovery of benzimidazole 5-carboxylic amide derivatives with low-nanomolar potency

  摘要：

  Optimization of benzimidazole 5-carboxamide derivatives previously identified as specific inhibitors of the NS5B polymerase of the hepatitis C virus (HCV) has led to the discovery of potent analogues that inhibit the enzyme at low-nanomolar concentrations. Greater than 800-fold improvement in potency from the original lead structure was achieved through the combined effects of conformational rigidification, molecular size extension and the identification of previously unexploited interactions. Furthermore, these inhibitors retain specificity for HCV polymerase relative to other viral and mammalian RNA polymerases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.032
• 作为产物：
  描述：

  甲醇 、 5-羟基-D-色氨酸 在 氯化亚砜 作用下， 生成 (R)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Non-nucleoside inhibitors of the hepatitis C virus NS5B polymerase: discovery of benzimidazole 5-carboxylic amide derivatives with low-nanomolar potency

  摘要：

  Optimization of benzimidazole 5-carboxamide derivatives previously identified as specific inhibitors of the NS5B polymerase of the hepatitis C virus (HCV) has led to the discovery of potent analogues that inhibit the enzyme at low-nanomolar concentrations. Greater than 800-fold improvement in potency from the original lead structure was achieved through the combined effects of conformational rigidification, molecular size extension and the identification of previously unexploited interactions. Furthermore, these inhibitors retain specificity for HCV polymerase relative to other viral and mammalian RNA polymerases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.032

文献信息

• Bionic synthesis of novel monoterpenoid indole alkaloid-like analogs with tyrosinase inhibition activity based on loganetin
  作者：Hong-mao Qiu、Lu-lu Deng、Jiang Li、Mei Zhang、Xiao-jiang Hao、Chun-mao Yuan、Peng Zhang、Shu-zhen Mu

  DOI：10.1016/j.molstruc.2024.138608

  日期：2024.9