N-(2-isopropoxy-5-(4-(2,2,2-trifluoroacetyl)piperazin-1-yl)phenyl)pyrazine-2-carboxamide | 1609122-93-1

• 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: N-(2-isopropoxy-5-(4-(2,2,2-trifluoroacetyl)piperazin-1-yl)phenyl)pyrazine-2-carboxamide
• CAS: 1609122-93-1
• 化学式: C₂₀H₂₂F₃N₅O₃
• 分子量: 437.422
• InChiKey: UUHBKGHBCZYLHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  87.66
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(2-isopropoxy-5-(4-(2,2,2-trifluoroacetyl)piperazin-1-yl)phenyl)pyrazine-2-carboxamide 在 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-(5-(4-(4-fluorobenzyl)piperazin-1-yl)-2-isopropoxyphenyl)pyrazine-2-carboxamide
  参考文献：
  名称：

  Design, syntheses, and characterization of piperazine based chemokine receptor CCR5 antagonists as anti prostate cancer agents

  摘要：

  Chemokine receptor CCR5 plays an important role in the pro-inflammatory environment that aids in the proliferation of prostate cancer cells. Previously, a series of CCR5 antagonists containing a piperidine ring core skeleton were designed based upon the proposed CCR5 antagonist pharmacophore from molecular modeling studies. The developed CCR5 antagonists were able to antagonize CCR5 at a micromolar level and inhibit the proliferation of metastatic prostate cancer cell lines. In order to further explore the structure-activity-relationship of the pharmacophore identified, the molecular scaffold was expanded to contain a piperazine ring as the core. A number of compounds that were synthesized showed promising anti prostate cancer activity and reasonable cytotoxicity profiles based on the biological characterization. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.03.073
• 作为产物：
  描述：

  1-(4-isopropoxyphenyl)piperazine 在 吡啶 、 palladium 10% on activated carbon 、 2,3,5,6-四溴-4-甲基-4-硝基-2,5-环己二烯-1-酮 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 70.0h， 生成 N-(2-isopropoxy-5-(4-(2,2,2-trifluoroacetyl)piperazin-1-yl)phenyl)pyrazine-2-carboxamide
  参考文献：
  名称：

  Design, syntheses, and characterization of piperazine based chemokine receptor CCR5 antagonists as anti prostate cancer agents

  摘要：

  Chemokine receptor CCR5 plays an important role in the pro-inflammatory environment that aids in the proliferation of prostate cancer cells. Previously, a series of CCR5 antagonists containing a piperidine ring core skeleton were designed based upon the proposed CCR5 antagonist pharmacophore from molecular modeling studies. The developed CCR5 antagonists were able to antagonize CCR5 at a micromolar level and inhibit the proliferation of metastatic prostate cancer cell lines. In order to further explore the structure-activity-relationship of the pharmacophore identified, the molecular scaffold was expanded to contain a piperazine ring as the core. A number of compounds that were synthesized showed promising anti prostate cancer activity and reasonable cytotoxicity profiles based on the biological characterization. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.03.073