3-[2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl]-4-fluoro-1H-indole-7-carboxylic acid | 389628-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl]-4-fluoro-1H-indole-7-carboxylic acid
• CAS: 389628-31-3
• 化学式: C₂₂H₁₈FN₃O₅
• 分子量: 423.4
• InChiKey: YGWDPXXUDQQHTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Methyl 3-[(4-benzoylpiperazin-1-yl)(oxo)acetyl]-4-fluoro-1H-indole-7-carboxylate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以86%的产率得到3-[2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl]-4-fluoro-1H-indole-7-carboxylic acid
  参考文献：
  名称：

  Inhibitors of HIV-1 attachment. Part 7: Indole-7-carboxamides as potent and orally bioavailable antiviral agents

  摘要：

  A series of substituted carboxamides at the indole C7 position of the previously described 4-fluoro-substituted indole HIV-1 attachment inhibitor 1 was synthesized and the SAR delineated. Heteroaryl carboxamide inhibitors that exhibited pM potency in the primary cell-based assay against a pseudotype virus expressing a JRFL envelope were identified. The simple methyl amide analog 4 displayed a promising in vitro profile, with its favorable HLM stability and membrane permeability translating into favorable pharmacokinetic properties in preclinical species. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.115

文献信息

• Composition and antiviral activity of substituted indoleoxoacetic piperazine derivatives
  申请人：——

  公开号：US20030069245A1

  公开（公告）日：2003-04-10

  This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with indoleoxoacetyl piperazine derivatives. These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. More particularly, the present invention relates to the treatment of HIV and AIDS.

  这项发明提供了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，该发明涉及吲哚酮乙酰哌嗪衍生物。这些化合物具有独特的抗病毒活性，无论是单独使用还是与其他抗病毒药物、抗感染药物、免疫调节剂或HIV进入抑制剂结合使用。更具体地，本发明涉及HIV和艾滋病的治疗。
• COMPOSITION AND ANTIVIRAL ACTIVITY OF SUBSTITUTED INDOLEOXOACETIC PIPERAZINE DERIVATIVES
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1299382A1

  公开（公告）日：2003-04-09
• EP1299382A4
  申请人：——

  公开号：EP1299382A4

  公开（公告）日：2004-02-11
• US6573262B2
  申请人：——

  公开号：US6573262B2

  公开（公告）日：2003-06-03
• [EN] COMPOSITION AND ANTIVIRAL ACTIVITY OF SUBSTITUTED INDOLEOXOACETIC PIPERAZINE DERIVATIVES<br/>[FR] COMPOSITION ET ACTIVITE ANTIVIRALE DE DERIVES DE PIPERAZINE INDOLEOXOACETIQUE SUBSTITUES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2002004440A1

  公开（公告）日：2002-01-17

  This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and mthod of use. In particular, the invention is converned with indoleoxoacetyl piperazine derivatives. These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. Mor particularly, the present invention relates to the treatment of HIV and AIDS.