ethyl (Z)-4-(3-bromo-2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)-2-hydroxy-4-oxobut-2-enoate | 1026775-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl (Z)-4-(3-bromo-2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)-2-hydroxy-4-oxobut-2-enoate
• CAS: 1026775-68-7
• 化学式: C₂₇H₃₀BrN₅O₅
• 分子量: 584.47
• InChiKey: UJHPJMCKBFHGPF-JCMHNJIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  127.86
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-4-(3-bromo-2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)-2-hydroxy-4-oxobut-2-enoate 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以49%的产率得到
  参考文献：
  名称：

  Design and synthesis of dual inhibitors of HIV reverse transcriptase and integrase: Introducing a diketoacid functionality into delavirdine

  摘要：

  Cost and toxicity problems associated with highly active antiretroviral therapy (HAART) in HIV/AIDS treatment could be alleviated by using designed multiple ligands (DMLs). Dual inhibitors of HIV reverse transcriptase (RT) and integrase (IN) were rationally designed by introducing a diketoacid (DKA) functionality into the tolerant C-5 site of RT inhibitor delavirdine. The resulting compounds all demonstrate good activity against both RT and IN in enzymatic assays and HIV in cell-based assay, whereas their C-7 regioisomers are all inactive in these assays. Balanced activities were observed with C-3 halogenated inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.007
• 作为产物：
  描述：

  1-(3-bromo-2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)ethanone 、 草酸二乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以45%的产率得到ethyl (Z)-4-(3-bromo-2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)-2-hydroxy-4-oxobut-2-enoate
  参考文献：
  名称：

  Design and synthesis of dual inhibitors of HIV reverse transcriptase and integrase: Introducing a diketoacid functionality into delavirdine

  摘要：

  Cost and toxicity problems associated with highly active antiretroviral therapy (HAART) in HIV/AIDS treatment could be alleviated by using designed multiple ligands (DMLs). Dual inhibitors of HIV reverse transcriptase (RT) and integrase (IN) were rationally designed by introducing a diketoacid (DKA) functionality into the tolerant C-5 site of RT inhibitor delavirdine. The resulting compounds all demonstrate good activity against both RT and IN in enzymatic assays and HIV in cell-based assay, whereas their C-7 regioisomers are all inactive in these assays. Balanced activities were observed with C-3 halogenated inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.007