4-{2-[4-(3-Isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-butyric acid methyl ester | 174502-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-{2-[4-(3-Isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-butyric acid methyl ester
• CAS: 174502-11-5
• 化学式: C₂₆H₃₃N₅O₄
• 分子量: 479.579
• InChiKey: KRTKZXXCYIEOOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  99.79
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-{2-[4-(3-Isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-butyric acid methyl ester 在 lithium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 N-((E)-(1S,2R)-2-Hydroxy-1-hydroxymethyl-heptadec-3-enyl)-4-{2-[4-(3-isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-butyramide
  参考文献：
  名称：

  Synthesis and Antiviral Activity of [2-[[4-[3-[(1-Methylethyl)amino]-2-Pyridyl]-1-Piperazinyl]Carbonyl]-1H-Indol-5-yl] (BHAP) Acylsphingosine HIV Reverse Transcriptase Inhibitors

  摘要：

  The galactosylceramide lipid is recognized and tightly complexed by the HIV-1 membrane glycoprotein gp120 in the initial step of viral infection of certain cells. The incorporation of an antiviral agent into this lipid offers the opportunity to target, via this recognition, the antiviral to the HIV virion and HIV-infected cell. Substitution of a sphingosinyl and a galactosylsphingosinyl segment on the C-5 indolyl substituent of the Upjohn 1-[3-(alkylamino)-2-pyridinyl]-4-(1H-indol-2-ylcarbonyl)-piperazine (BHAP) HIV-1 reverse transcriptase inhibitor gave a set of ersatz ceramides (exemplified by 8 and 21) in which the antiretroviral agent substitutes at the position of the ceramide fatty acid. These sphingosine conjugates retain the full antiviral activity of the BHAP parent in an acute lymphatic cell culture antiviral assay. (C) 1995 Academic Press, Inc.

  DOI：

  10.1006/bioo.1995.1035
• 作为产物：
  描述：

  4-溴丁酸甲酯 、 1-[5-hydroxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine 在 potassium carbonate 作用下， 生成 4-{2-[4-(3-Isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-butyric acid methyl ester
  参考文献：
  名称：

  Synthesis and Antiviral Activity of [2-[[4-[3-[(1-Methylethyl)amino]-2-Pyridyl]-1-Piperazinyl]Carbonyl]-1H-Indol-5-yl] (BHAP) Acylsphingosine HIV Reverse Transcriptase Inhibitors

  摘要：

  The galactosylceramide lipid is recognized and tightly complexed by the HIV-1 membrane glycoprotein gp120 in the initial step of viral infection of certain cells. The incorporation of an antiviral agent into this lipid offers the opportunity to target, via this recognition, the antiviral to the HIV virion and HIV-infected cell. Substitution of a sphingosinyl and a galactosylsphingosinyl segment on the C-5 indolyl substituent of the Upjohn 1-[3-(alkylamino)-2-pyridinyl]-4-(1H-indol-2-ylcarbonyl)-piperazine (BHAP) HIV-1 reverse transcriptase inhibitor gave a set of ersatz ceramides (exemplified by 8 and 21) in which the antiretroviral agent substitutes at the position of the ceramide fatty acid. These sphingosine conjugates retain the full antiviral activity of the BHAP parent in an acute lymphatic cell culture antiviral assay. (C) 1995 Academic Press, Inc.

  DOI：

  10.1006/bioo.1995.1035