4-({5-Bromo-2-[(1-phenylpyrrolidin-3-yl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile | 1240422-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-({5-Bromo-2-[(1-phenylpyrrolidin-3-yl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile
• 英文别名: 4-[5-bromo-2-[(1-phenylpyrrolidin-3-yl)amino]pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile
• CAS: 1240422-99-4
• 化学式: C₂₃H₂₂BrN₅O
• 分子量: 464.365
• InChiKey: GEDMPRKAYRJRKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-[(5-bromo-2-chloropyrimidin-4-yl)oxy]-3,5-dimethylbenzonitrile 、 1-苯基吡咯烷-3-胺 在 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 4-({5-Bromo-2-[(1-phenylpyrrolidin-3-yl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile
  参考文献：
  名称：

  Discovery of piperidin-4-yl-aminopyrimidines as HIV-1 reverse transcriptase inhibitors. N-Benzyl derivatives with broad potency against resistant mutant viruses

  摘要：

  An analysis of the binding motifs of known HIV-1 non-nucleoside reverse transcriptase inhibitors has led to discovery of novel piperidine-linked aminopyrimidine derivatives with broad activity against wildtype as well as drug-resistant mutant viruses. Notably, the series retains potency against the K103 N/Y181C and Y188L mutants, among others. Thus, the N-benzyl compound 5k has a particularly attractive pro. le. Synthesis and SAR are presented and discussed, as well as crystal structures relating to the binding motifs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.040

文献信息

• Discovery of piperidin-4-yl-aminopyrimidines as HIV-1 reverse transcriptase inhibitors. N-Benzyl derivatives with broad potency against resistant mutant viruses
  作者：Denis J. Kertesz、Christine Brotherton-Pleiss、Minmin Yang、Zhanguo Wang、Xianfeng Lin、Zongxing Qiu、Donald R. Hirschfeld、Shelley Gleason、Taraneh Mirzadegan、Pete W. Dunten、Seth F. Harris、Armando G. Villaseñor、Julie Qi Hang、Gabrielle M. Heilek、Klaus Klumpp

  DOI：10.1016/j.bmcl.2010.05.040

  日期：2010.7

  An analysis of the binding motifs of known HIV-1 non-nucleoside reverse transcriptase inhibitors has led to discovery of novel piperidine-linked aminopyrimidine derivatives with broad activity against wildtype as well as drug-resistant mutant viruses. Notably, the series retains potency against the K103 N/Y181C and Y188L mutants, among others. Thus, the N-benzyl compound 5k has a particularly attractive pro. le. Synthesis and SAR are presented and discussed, as well as crystal structures relating to the binding motifs. (C) 2010 Elsevier Ltd. All rights reserved.