1-[5-hydroxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine | 136816-97-2

• 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: 1-[5-hydroxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine
• 英文别名: Piperazine, 1-((5-hydroxy-1H-indol-2-yl)carbonyl)-4-(3-((1-methylethyl)amino)-2-pyridinyl)-；(5-hydroxy-1H-indol-2-yl)-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl]methanone
• CAS: 136816-97-2
• 化学式: C₂₁H₂₅N₅O₂
• 分子量: 379.462
• InChiKey: AHNZDDRXVDLYMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[5-hydroxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine 在 lithium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 12.5h， 生成 6-{2-[4-(3-Isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yloxy}-hexanoic acid
  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：

  1-[5-苄氧基吲哚基-2-羰基]-4-[3-(1-甲基乙基)氨基-2-吡啶基]哌嗪 生成 1-[5-hydroxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine
  参考文献：
  名称：

  Anti-aids piperazines

  摘要：

  本发明包括二芳基取代的杂环化合物（III）##STR1##，其可用于治疗感染HIV病毒的个体。本发明还包括某些先前一般性披露的抗艾滋病哌嗪基化合物（V）以及一种使用吲哚类化合物（V）和抗艾滋病胺类（X）治疗HIV感染个体的方法。

  公开号：

  US05489593A1

文献信息

• Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogs and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)carbonyl]-4-[3-[(1-methylethyl)amino]pyridinyl]piperazinemonomethanesulfonate (U-90152S), a second-generation clinical candidate
  作者：Donna L. Romero、Raymond A. Morge、Michael J. Genin、Carolyn Biles、Mariano Busso、Lionel Resnick、Irene W. Althaus、Fritz Reusser、Richard C. Thomas、William G. Tarpley

  DOI：10.1021/jm00062a027

  日期：1993.5
• Anti-aids piperazines
  申请人：The Upjohn Company

  公开号：US05489593A1

  公开（公告）日：1996-02-06

  The present invention includes diaromatic substituted heterocyclic compounds (III) ##STR1## which are useful in treating individuals infected with the HIV virus. The invention includes certain previously generically disclosed anti-AIDS piperazinyl compounds (V) and a method of treating HIV infected individuals with the indoles of formula (V) and the anti-AIDS amines (X).

  本发明包括二芳基取代的杂环化合物（III）##STR1##，其可用于治疗感染HIV病毒的个体。本发明还包括某些先前一般性披露的抗艾滋病哌嗪基化合物（V）以及一种使用吲哚类化合物（V）和抗艾滋病胺类（X）治疗HIV感染个体的方法。
• 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
  作者：I. Islam、R.R. Hinshaw、K.T. Chong、A. Kato、R.T. Borchardt、J.F. Fisher

  DOI：10.1006/bioo.1995.1035

  日期：1995.12

  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.