1-(trifluoromethyl)-4-(4-isopropoxy-3-nitrophenyl)piperazine | 1364525-13-2

• 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: 1-(trifluoromethyl)-4-(4-isopropoxy-3-nitrophenyl)piperazine
• 英文别名: 2,2,2-Trifluoro-1-[4-(3-nitro-4-propan-2-yloxyphenyl)piperazin-1-yl]ethanone；2,2,2-trifluoro-1-[4-(3-nitro-4-propan-2-yloxyphenyl)piperazin-1-yl]ethanone
• CAS: 1364525-13-2
• 化学式: C₁₅H₁₈F₃N₃O₄
• 分子量: 361.321
• InChiKey: MPCTZYQMEFMIFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(trifluoromethyl)-4-(4-isopropoxy-3-nitrophenyl)piperazine 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 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 、 potassium iodide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 50.5h， 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 、 2,3,5,6-四溴-4-甲基-4-硝基-2,5-环己二烯-1-酮 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 1-(trifluoromethyl)-4-(4-isopropoxy-3-nitrophenyl)piperazine
  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

文献信息

• Facile synthesis of 2,3,5,6-tetrabromo-4-methyl-nitrocyclohexa-2,5-dien-1-one, a mild nitration reagent
  作者：Christopher K. Arnatt、Yan Zhang

  DOI：10.1016/j.tetlet.2012.01.066

  日期：2012.3

  Nitrocylcohexadienones have been applied as nitration reagents for mild, mono-nitrating reactions. The original synthesis of 2,3,5,6-tetrabromo-4-methyl-4-nitrocylcohexa-2,5-dien-1-one appeared to be difficult to pursue due to both the solvent system and reaction conditions. Therefore, we applied a modified solvent system and optimized the reaction conditions to prepare the dienone at 0 degrees C, to eventually overcome the difficulties. Published by Elsevier Ltd.
• Design, syntheses, and characterization of piperazine based chemokine receptor CCR5 antagonists as anti prostate cancer agents
  作者：Christopher K. Arnatt、Joanna L. Adams、Zhu Zhang、Kendra M. Haney、Guo Li、Yan Zhang

  DOI：10.1016/j.bmcl.2014.03.073

  日期：2014.5

  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.