Piperazine, 4-benzoyl-1-[2-(4-fluoro-1H-indol-3-yl)-1,2-dioxoethyl]-2-methyl- | 313335-38-5

• 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: Piperazine, 4-benzoyl-1-[2-(4-fluoro-1H-indol-3-yl)-1,2-dioxoethyl]-2-methyl-
• 英文别名: 1-(4-benzoyl-2-methylpiperazin-1-yl)-2-(4-fluoro-1H-indol-3-yl)ethane-1,2-dione
• CAS: 313335-38-5
• 化学式: C₂₂H₂₀FN₃O₃
• 分子量: 393.418
• InChiKey: GJIOAZQCBADHSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Piperazine, 4-benzoyl-1-[2-(4-fluoro-1H-indol-3-yl)-1,2-dioxoethyl]-2-methyl- 生成 N-(Benzoyl)-(R)-3-methyl-N'-[(4-fluoro-indol-3-yl)-oxoacetyl]-piperazine 、 1-[(2S)-4-benzoyl-2-methyl-piperazin-1-yl]-2-(4-fluoro-1H-indol-3-yl)ethane-1,2-dione
  参考文献：
  名称：

  Inhibitors of HIV-1 attachment. Part 4: A study of the effect of piperazine substitution patterns on antiviral potency in the context of indole-based derivatives

  摘要：

  4-Fluoro- and 4-methoxy-1-(4-benzoylpiperazin-1-yl)-2-(1H-indol-3-yl) ethane-1,2-dione (2 and 3, respectively) have been characterized as potent inhibitors of HIV-1 attachment that interfere with the interaction of viral gp120 with the host cell receptor CD4. As part of an effort to understand fundamental aspects of this pharmacophore, discovered originally using a high throughput cell-based screen, modification and substitution of the piperazine ring was examined in the context of compounds 6a-ah. The piperazine ring was shown to be a critical element of the HIV-1 attachment inhibiting pharmacophore, acting as a scaffold to deploy the indole glyoxamide and benzamide in a topographical relationship that complements the binding site on gp120. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.076

文献信息

• Inhibitors of HIV-1 attachment. Part 4: A study of the effect of piperazine substitution patterns on antiviral potency in the context of indole-based derivatives
  作者：Tao Wang、John F. Kadow、Zhongxing Zhang、Zhiwei Yin、Qi Gao、Dedong Wu、Dawn DiGiugno Parker、Zheng Yang、Lisa Zadjura、Brett A. Robinson、Yi-Fei Gong、Wade S. Blair、Pei-Yong Shi、Gregory Yamanaka、Pin-Fang Lin、Nicholas A. Meanwell

  DOI：10.1016/j.bmcl.2009.07.076

  日期：2009.9

  4-Fluoro- and 4-methoxy-1-(4-benzoylpiperazin-1-yl)-2-(1H-indol-3-yl) ethane-1,2-dione (2 and 3, respectively) have been characterized as potent inhibitors of HIV-1 attachment that interfere with the interaction of viral gp120 with the host cell receptor CD4. As part of an effort to understand fundamental aspects of this pharmacophore, discovered originally using a high throughput cell-based screen, modification and substitution of the piperazine ring was examined in the context of compounds 6a-ah. The piperazine ring was shown to be a critical element of the HIV-1 attachment inhibiting pharmacophore, acting as a scaffold to deploy the indole glyoxamide and benzamide in a topographical relationship that complements the binding site on gp120. (C) 2009 Elsevier Ltd. All rights reserved.