3-羟基-4-甲基-1H-吲哚-2-羧酸乙酯 | 153501-38-3

• 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
• 中文名称: 3-羟基-4-甲基-1H-吲哚-2-羧酸乙酯
• 英文名称: ethyl 3-hydroxy-4-methyl-1H-indole-2-carboxylate
• CAS: 153501-38-3
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: WXNNDCUHYBVEKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-4-甲基-1H-吲哚-2-羧酸乙酯 在 sodium hydroxide 、 四丁基溴化铵 、 氨 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 36.5h， 生成 1,2,3,4-tetrahydro-10-methoxy-9-methylpyrazino[1,2-a]indol-1-one
  参考文献：
  名称：

  Synthesis, pharmacology and therapeutic potential of 10-methoxypyrazino[1,2-a]indoles, partial agonists at the 5HT2C receptor

  摘要：

  A series of new 10-methoxypyrazino[1,2-a]indoles has been prepared and shown to be 5HT(2C) receptor ligands. The studied compounds 10a-j were found to act as partial agonists at the 5HT(2C) receptor, binding with high affinity and moderate selectivity versus 5HT(1A) and 5HT(2A) receptors, but inducing only a submaximal increase in phosphoinositol formation. Compound 10j was demonstrated to be active in animal models of obsessive-compulsive disorder, depression and panic anxiety.

  DOI：

  10.1016/s0223-5234(97)83976-1
• 作为产物：
  描述：

  ethyl N-[2-(ethoxycarbonyl)-3-methylphenyl]glycinate 在 sodium 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 2.0h， 以77%的产率得到3-羟基-4-甲基-1H-吲哚-2-羧酸乙酯
  参考文献：
  名称：

  Synthesis, pharmacology and therapeutic potential of 10-methoxypyrazino[1,2-a]indoles, partial agonists at the 5HT2C receptor

  摘要：

  A series of new 10-methoxypyrazino[1,2-a]indoles has been prepared and shown to be 5HT(2C) receptor ligands. The studied compounds 10a-j were found to act as partial agonists at the 5HT(2C) receptor, binding with high affinity and moderate selectivity versus 5HT(1A) and 5HT(2A) receptors, but inducing only a submaximal increase in phosphoinositol formation. Compound 10j was demonstrated to be active in animal models of obsessive-compulsive disorder, depression and panic anxiety.

  DOI：

  10.1016/s0223-5234(97)83976-1

文献信息

• Identification of 3-Oxindole Derivatives as Small Molecule HIV-1 Inhibitors Targeting Tat-Mediated Viral Transcription
  作者：Dong-Eun Kim、Young Hyun Shin、Jung-Eun Cho、Subeen Myung、Hong Gi Kim、Kyung-Chang Kim、Chul Min Park、Cheol-Hee Yoon

  DOI：10.3390/molecules27154921

  日期：——

  The heterocyclic indole structure has been shown to be one of the most promising scaffolds, offering various medicinal advantages from its wide range of biological activity. Nonetheless, the significance of 3-oxindole has been less known. In this study, a series of novel 3-oxindole-2-carboxylates were synthesized and their antiviral activity against human immunodeficiency virus-1 (HIV-1) infection was evaluated. Among these, methyl (E)-2-(3-chloroallyl)-4,6-dimethyl-one (6f) exhibited the most potent inhibitory effect on HIV-1 infection, with a half-maximal inhibitory concentration (IC50) of 0.4578 μM but without severe cytotoxicity (selectivity index (SI) = 111.37). The inhibitory effect of these compounds on HIV-1 infection was concordant with their inhibitory effect on the viral replication cycle. Mode-of-action studies have shown that these prominent derivatives specifically inhibited the Tat-mediated viral transcription on the HIV-1 LTR promoter instead of reverse transcription or integration. Overall, our findings indicate that 3-oxindole derivatives could be useful as a potent scaffold for the development of a new class of anti-HIV-1 agents.

  杂环吲哚结构被证明是最有前途的支架之一，从其广泛的生物活性中提供了各种药理优势。然而，3-氧代吲哚的重要性却较少被了解。在这项研究中，合成了一系列新型的3-氧代吲哚-2-羧酸酯，并评估了它们对人类免疫缺陷病毒-1（HIV-1）感染的抗病毒活性。其中，甲基（E）-2-（3-氯丙烯基）-4,6-二甲基-1-酮（6f）表现出对HIV-1感染最强的抑制效果，半数抑制浓度（IC50）为0.4578μM，但没有严重的细胞毒性（选择性指数（SI）= 111.37）。这些化合物对HIV-1感染的抑制效果与它们对病毒复制周期的抑制效果一致。作用模式研究表明，这些杰出的衍生物特异性地抑制了Tat介导的HIV-1 LTR启动子上的病毒转录，而不是逆转录或整合。总体而言，我们的研究结果表明，3-氧代吲哚衍生物可以作为一种有前途的支架，用于开发新型的抗HIV-1药物。
• Synthesis, pharmacology and therapeutic potential of 10-methoxypyrazino[1,2-a]indoles, partial agonists at the 5HT2C receptor
  作者：M Bös、F Jenck、JR Martin、JL Moreau、V Mutel、AJ Sleight、U Widmer

  DOI：10.1016/s0223-5234(97)83976-1

  日期：1997.1

  A series of new 10-methoxypyrazino[1,2-a]indoles has been prepared and shown to be 5HT(2C) receptor ligands. The studied compounds 10a-j were found to act as partial agonists at the 5HT(2C) receptor, binding with high affinity and moderate selectivity versus 5HT(1A) and 5HT(2A) receptors, but inducing only a submaximal increase in phosphoinositol formation. Compound 10j was demonstrated to be active in animal models of obsessive-compulsive disorder, depression and panic anxiety.