Methyl 3-[(4-benzoylpiperazin-1-yl)(oxo)acetyl]-4-fluoro-1H-indole-7-carboxylate | 389628-30-2

• 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: Methyl 3-[(4-benzoylpiperazin-1-yl)(oxo)acetyl]-4-fluoro-1H-indole-7-carboxylate
• 英文别名: methyl 3-[2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl]-4-fluoro-1H-indole-7-carboxylate
• CAS: 389628-30-2
• 化学式: C₂₃H₂₀FN₃O₅
• 分子量: 437.427
• InChiKey: ZVOYAFUJOZIYTH-UHFFFAOYSA-N

物化性质

• 沸点：
  662.0±65.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  99.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  7-溴-4-氟吲哚 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 Methyl 3-[(4-benzoylpiperazin-1-yl)(oxo)acetyl]-4-fluoro-1H-indole-7-carboxylate
  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