1-(4-benzoylpiperazin-1-yl)-2-(5-chloro-7-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)ethane-1,2-dione | 1417339-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-(4-benzoylpiperazin-1-yl)-2-(5-chloro-7-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)ethane-1,2-dione
• CAS: 1417339-72-0
• 化学式: C₂₁H₁₉ClN₄O₃
• 分子量: 410.86
• InChiKey: QXUAEYJEOUPCIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-benzoylpiperazin-1-yl)-2-(5-chloro-7-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)ethane-1,2-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以90%的产率得到1-(4-benzoylpiperazin-1-yl)-2-(7-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)ethane-1,2-dione
  参考文献：
  名称：

  Inhibitors of HIV-1 attachment. Part 10. The discovery and structure–activity relationships of 4-azaindole cores

  摘要：

  A series of 4-azaindole oxoacetic acid piperazine benzamides was synthesized and evaluated in an effort to identify an oral HIV-1 attachment inhibitor with the potential to improve upon the pre-clinical profile of BMS-378806 (7), an initial clinical compound. Modifications at the 7-position of the 4-azaindole core modulated potency significantly and SAR showed that certain compounds with a 5-membered ring heteroaryl group at that position were the most potent. Four of the compounds with the best profiles were evaluated in a rat pharmacokinetic model and all had superior oral bioavailability and lower clearance when compared with 7. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.120
• 作为产物：
  描述：

  2-氯-5-硝基-4-甲基吡啶 在 aluminum (III) chloride 、 potassium carbonate 、 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-benzoylpiperazin-1-yl)-2-(5-chloro-7-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)ethane-1,2-dione
  参考文献：
  名称：

  Inhibitors of HIV-1 attachment. Part 10. The discovery and structure–activity relationships of 4-azaindole cores

  摘要：

  A series of 4-azaindole oxoacetic acid piperazine benzamides was synthesized and evaluated in an effort to identify an oral HIV-1 attachment inhibitor with the potential to improve upon the pre-clinical profile of BMS-378806 (7), an initial clinical compound. Modifications at the 7-position of the 4-azaindole core modulated potency significantly and SAR showed that certain compounds with a 5-membered ring heteroaryl group at that position were the most potent. Four of the compounds with the best profiles were evaluated in a rat pharmacokinetic model and all had superior oral bioavailability and lower clearance when compared with 7. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.120

文献信息

• Inhibitors of HIV-1 attachment. Part 10. The discovery and structure–activity relationships of 4-azaindole cores
  作者：Tao Wang、Zhong Yang、Zhongxing Zhang、Yi-Fei Gong、Keith A. Riccardi、Pin-Fang Lin、Dawn D. Parker、Sandhya Rahematpura、Marina Mathew、Ming Zheng、Nicholas A. Meanwell、John F. Kadow、John A. Bender

  DOI：10.1016/j.bmcl.2012.10.120

  日期：2013.1

  A series of 4-azaindole oxoacetic acid piperazine benzamides was synthesized and evaluated in an effort to identify an oral HIV-1 attachment inhibitor with the potential to improve upon the pre-clinical profile of BMS-378806 (7), an initial clinical compound. Modifications at the 7-position of the 4-azaindole core modulated potency significantly and SAR showed that certain compounds with a 5-membered ring heteroaryl group at that position were the most potent. Four of the compounds with the best profiles were evaluated in a rat pharmacokinetic model and all had superior oral bioavailability and lower clearance when compared with 7. (C) 2012 Elsevier Ltd. All rights reserved.