(+)-m-Nitrobiphenyline | 945618-95-1

• 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: (+)-m-Nitrobiphenyline
• 英文别名: (R)-(+)-m-nitrobiphenyline；(R)-2-[1-(3'-nitrobiphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole；(R)-3-Nitrobiphenyline；2-[(1R)-1-[2-(3-nitrophenyl)phenoxy]ethyl]-4,5-dihydro-1H-imidazole
• CAS: 945618-95-1
• 化学式: C₁₇H₁₇N₃O₃
• 分子量: 311.34
• InChiKey: NMSAVNXFCXMJJY-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-m-Nitrobiphenyline 、 (R)-(+)-1-苯乙基异氰酸酯 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (R)-2-[1-(3'-nitrobiphenyl-2-yloxy)ethyl]-4,5-dihydroimidazole-1-carboxylic acid [(R)-1-phenylethyl]amide
  参考文献：
  名称：

  α₂-Adrenoreceptors Profile Modulation. 3. (R)-(+)-m-Nitrobiphenyline, a New Efficient and α_2C-Subtype Selective Agonist

  摘要：

  To assess the stereochemical requirements for efficient (alpha(2C)-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(+/-)-5] were prepared and tested on cells expressing the human alpha(2)-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was much more efficient than (S)-(-)-5 in producing (alpha(2C)-activation. Surprising reversal of enantioselectivity was observed with respect to structurally similar biphenyline [(+/-)-l] whose (S)-(-)-form proved the preferred (alpha(2C)-configuration.

  DOI：

  10.1021/jm061487a
• 作为产物：
  描述：

  2-(3-硝基苯基)苯酚 在 吡啶 、 盐酸 、 potassium methanolate 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 丁酮 为溶剂， 反应 42.0h， 生成 (+)-m-Nitrobiphenyline
  参考文献：
  名称：

  α₂-Adrenoreceptors Profile Modulation. 3. (R)-(+)-m-Nitrobiphenyline, a New Efficient and α_2C-Subtype Selective Agonist

  摘要：

  To assess the stereochemical requirements for efficient (alpha(2C)-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(+/-)-5] were prepared and tested on cells expressing the human alpha(2)-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was much more efficient than (S)-(-)-5 in producing (alpha(2C)-activation. Surprising reversal of enantioselectivity was observed with respect to structurally similar biphenyline [(+/-)-l] whose (S)-(-)-form proved the preferred (alpha(2C)-configuration.

  DOI：

  10.1021/jm061487a

文献信息

• Fruitful Adrenergic α_2C-Agonism/α_2A-Antagonism Combination to Prevent and Contrast Morphine Tolerance and Dependence^,
  作者：Fabio Del Bello、Laura Mattioli、Francesca Ghelfi、Mario Giannella、Alessandro Piergentili、Wilma Quaglia、Claudia Cardinaletti、Marina Perfumi、Russell J. Thomas、Ugo Zanelli、Carla Marchioro、Michele Dal Cin、Maria Pigini

  DOI：10.1021/jm100977d

  日期：2010.11.11

  The functional in vitro study of the enantiomers of imidazolines 4-7 highlighted the role played by the nature of the ortho phenyl substituent in determining the preferred alpha(2C)-AR configuration. Indeed, the (S) enantiomers of 4-6 or (R) enantiomer of 7 behave as eutomers and activate this subtype as full agonists; the corresponding distomers are partial agonists. Because in clinical pain management with opioids alpha(2C)-AR agonists, devoid of the alpha(2A)-AR-mediated side effects, may represent an improvement over current therapies with clonidine like drugs, 4 and its enantiomers, showing alpha(2C)-agonism/alpha(2A)-Aantagonism, have been studied in vivo. The data suggest that partial alpha(2C)-activation is compatible with effective enhancement of morphine analgesia and reduction both of morphine tolerance acquisition and morphine dependence acquisition and expression. On the contrary, full alpha(2C)-activation appears advantageous in reducing morphine tolerance expression. Interestingly, the biological profile displayed by 4 (allyphenyline) and its eutomer (S)-(+)-4 has been found to be very unusual.
• α₂-Adrenoreceptors Profile Modulation. 3. (<i>R</i>)-(+)-<i>m</i>-Nitrobiphenyline, a New Efficient and α_2C-Subtype Selective Agonist
  作者：Pierre-Antoine Crassous、Claudia Cardinaletti、Antonio Carrieri、Bruno Bruni、Massimo Di Vaira、Francesco Gentili、Francesca Ghelfi、Mario Giannella、Hervé Paris、Alessandro Piergentili、Wilma Quaglia、Stéphane Schaak、Cristian Vesprini、Maria Pigini

  DOI：10.1021/jm061487a

  日期：2007.8.1

  To assess the stereochemical requirements for efficient (alpha(2C)-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(+/-)-5] were prepared and tested on cells expressing the human alpha(2)-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was much more efficient than (S)-(-)-5 in producing (alpha(2C)-activation. Surprising reversal of enantioselectivity was observed with respect to structurally similar biphenyline [(+/-)-l] whose (S)-(-)-form proved the preferred (alpha(2C)-configuration.