1-(1H-indol-3-yl)-2-(piperazin-1-yl)ethane-1,2-dione | 313337-36-9

• 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: 1-(1H-indol-3-yl)-2-(piperazin-1-yl)ethane-1,2-dione
• 英文别名: 1-(1H-indol-3-yl)-2-piperazin-1-ylethane-1,2-dione
• CAS: 313337-36-9
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: UMHDILXFWJTACP-UHFFFAOYSA-N

物化性质

• 沸点：
  484.7±55.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  间氟苯甲酸 、 1-(1H-indol-3-yl)-2-(piperazin-1-yl)ethane-1,2-dione 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-[4-(3-fluorobenzoyl)piperazin-1-yl]-2-(1H-indol-3-yl)ethane-1,2-dione
  参考文献：
  名称：

  Inhibitors of HIV-1 attachment. Part 3: A preliminary survey of the effect of structural variation of the benzamide moiety on antiviral activity

  摘要：

  1-(4-Benzoylpiperazin-1-yl)-2-(1H-indol-3-yl) ethane-1,2-dione (1a) has been characterized as an inhibitor of HIV-1 attachment that interferes with the interaction of viral gp120 with the host cell receptor CD4. In previous studies, the effect of indole substitution pattern on antiviral activity was probed. In this Letter, the effect of structural variation of the benzamide moiety is described, a study that reveals the potential or the phenyl moiety to be replaced by five-membered heterocyclic rings and a restricted tolerance for the introduction of substituents to the phenyl ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.027
• 作为产物：
  描述：

  1-(tert-butoxycarbonyl)-4-[2-(indol-3-yl)-2-oxoacetyl]piperazine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-(1H-indol-3-yl)-2-(piperazin-1-yl)ethane-1,2-dione
  参考文献：
  名称：

  Inhibitors of HIV-1 attachment. Part 3: A preliminary survey of the effect of structural variation of the benzamide moiety on antiviral activity

  摘要：

  1-(4-Benzoylpiperazin-1-yl)-2-(1H-indol-3-yl) ethane-1,2-dione (1a) has been characterized as an inhibitor of HIV-1 attachment that interferes with the interaction of viral gp120 with the host cell receptor CD4. In previous studies, the effect of indole substitution pattern on antiviral activity was probed. In this Letter, the effect of structural variation of the benzamide moiety is described, a study that reveals the potential or the phenyl moiety to be replaced by five-membered heterocyclic rings and a restricted tolerance for the introduction of substituents to the phenyl ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.027

文献信息

• Anti-AIDS agents 86. Synthesis and anti-HIV evaluation of 2′,3′-seco-3′-nor DCP and DCK analogues
  作者：Ying Chen、Ming Cheng、Fa-Qiang Liu、Peng Xia、Keduo Qian、Donglei Yu、Yi Xia、Zheng-Yu Yang、Chin-Ho Chen、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1016/j.ejmech.2011.07.051

  日期：2011.10

  In a continuing study of novel anti-HIV agents with drug-like structures and properties, 30 1′-O-, 1′-S-, 4′-O- and 4′-substituted-2′,3′-seco-3′-nor DCP and DCK analogues (8-37) were designed and synthesized. All newly synthesized seco-compounds were screened against HIV-1NL4-3 and a multiple reverse transcriptase (RT) inhibitor-resistant (RTMDR) strain in the TZM-bl cell line, using seco-DCK (7) and

  在对具有类似药物结构和特性的新型抗 HIV 药物的持续研究中，30 1'- O -、1'- S -、4'- O - 和 4'-取代-2',3'-seco-设计并合成了3'-nor DCP 和 DCK 类似物 ( 8-37 )。所有新合成的开环化合物进行了筛选抗HIV-1 NL4-3和在TZM-BL细胞系的倍数逆转录酶（RT）抑制剂抗性（RTMDR）株，使用开环- DCK（7）和2-乙基DCP ( 4 ) 作为对照。几种化合物（14，18，19，22-24，和32）显示出有效的抗HIV活性，EC50 个值范围从 0.93 到 1.93 μM，治疗指数 (TI) 值范围从 20 到39。1'- O -Isopropoxy-2',3'-seco-3'-nor-DCP ( 12 ) 显示出最大的效力新合成的化合物对 HIV-1 NL4-3和 RTMDR 菌株的EC 50值分别为 0.47 和 0.88
• Piperazine Enamines as Antiviral Agents
  申请人：Wang Tao

  公开号：US20070287712A1

  公开（公告）日：2007-12-13

  This disclosure provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the disclosure is concerned with indole and azaindole piperazine enamine derivatives that possess unique antiviral activity. More particularly, the present disclosure relates to compounds useful for the treatment of HIV and AIDS.

  本公开提供具有药物和生物影响性质的化合物，它们的药物组合物和使用方法。具体而言，本公开涉及具有独特抗病毒活性的吲哚和氮杂吲哚哌嗪烯胺衍生物。更具体地说，本公开涉及用于治疗艾滋病毒和艾滋病的化合物。
• Piperazine enamines as antiviral agents
  申请人：Bristol-Meyers Squibb Company

  公开号：US07504399B2

  公开（公告）日：2009-03-17

  This disclosure provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the disclosure is concerned with indole and azaindole piperazine enamine derivatives that possess unique antiviral activity. More particularly, the present disclosure relates to a compound of Formula I useful for the treatment of HIV and AIDS.

  本公开提供具有药物和生物影响性质的化合物，它们的制药组合物和使用方法。具体而言，本公开涉及具有独特抗病毒活性的吲哚和氮杂吲哚哌嗪烯胺衍生物。更具体地说，本公开涉及一种式I的化合物，用于治疗HIV和艾滋病。
• PIPERAZINE ENAMINES AS ANTIVIRAL AGENTS
  申请人：Bristol-Myers Squibb Company

  公开号：EP2029532A2

  公开（公告）日：2009-03-04
• US7504399B2
  申请人：——

  公开号：US7504399B2

  公开（公告）日：2009-03-17