3-乙氧羰基-1-(4-甲氧基苯基)-5-苯基-1H-吡唑 | 62160-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-乙氧羰基-1-(4-甲氧基苯基)-5-苯基-1H-吡唑
• 英文名称: 3-ethoxycarbonyl-1-(4-methoxyphenyl)-5-phenyl-1H-pyrazole
• 英文别名: 1-(4-methoxy-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester；ethyl 1-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-3-carboxylate；ethyl 1-(4-methoxyphenyl)-5-phenylpyrazole-3-carboxylate
• CAS: 62160-90-1
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: OGTIHBXYRARJEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  103 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  493.1±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-乙氧羰基-1-(4-甲氧基苯基)-5-苯基-1H-吡唑 在 四溴化碳 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-bromomethyl-1-(4-methoxyphenyl)-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  Pyrazole CCK1 receptor antagonists. Part 1: Solution-phase library synthesis and determination of Free–Wilson additivity

  摘要：

  High throughput screening revealed compound 1 as a potent antagonist of the CCK1 receptor. Evaluation of the CCK1 SAR in a series of these diarylpyrazole antagonists was conducted in a matrix synthesis format revealing additive (Free-Wilson) and non-additive SAR. This use of additive QSAR modeling in conjunction with combinatorial libraries represents a unique approach to the evaluation of SAR interactions between the variables of any combinatorial matrix. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.048
• 作为产物：
  描述：

  ethyl 4-hydroxy-2-oxo-4-phenylbut-3-enoate 、 (4-甲氧基苯基)肼 以 乙醇 为溶剂， 反应 3.0h， 以78%的产率得到3-乙氧羰基-1-(4-甲氧基苯基)-5-苯基-1H-吡唑
  参考文献：
  名称：

  New COX-2/5-LOX Inhibitors:  Apoptosis-Inducing Agents Potentially Useful in Prostate Cancer Chemotherapy

  摘要：

  The arachidonic acid metabolizing enzymes cyclooxygenase-2 (COX-2) and lipoxygenases (LOXs) have been found to be implicated in a variety of cancers, including prostate cancer. To develop new therapeutic treatments, it therefore seemed interesting to design dual COX-2/5-LOX inhibitors. We report here the synthesis and in vitro pharmacological properties of diarylpyrazole derivatives that have in their structure key pharmacophoric elements to obtain optimal interaction with subsites of active pockets in both enzyme systems. Using a molecular modeling approach, a set of SAR data is proposed, highlighting the importance of the sulfonyl group of one of the aryl moieties in terms of proliferation inhibition and/or apoptosis induction.

  DOI：

  10.1021/jm0407761

文献信息

• New COX-2/5-LOX Inhibitors:  Apoptosis-Inducing Agents Potentially Useful in Prostate Cancer Chemotherapy
  作者：Nicole Pommery、Thierry Taverne、Aurélie Telliez、Laurence Goossens、Caroline Charlier、Jean Pommery、Jean-François Goossens、Raymond Houssin、François Durant、Jean-Pierre Hénichart

  DOI：10.1021/jm0407761

  日期：2004.12.1

  The arachidonic acid metabolizing enzymes cyclooxygenase-2 (COX-2) and lipoxygenases (LOXs) have been found to be implicated in a variety of cancers, including prostate cancer. To develop new therapeutic treatments, it therefore seemed interesting to design dual COX-2/5-LOX inhibitors. We report here the synthesis and in vitro pharmacological properties of diarylpyrazole derivatives that have in their structure key pharmacophoric elements to obtain optimal interaction with subsites of active pockets in both enzyme systems. Using a molecular modeling approach, a set of SAR data is proposed, highlighting the importance of the sulfonyl group of one of the aryl moieties in terms of proliferation inhibition and/or apoptosis induction.
• Pyrazole CCK1 receptor antagonists. Part 1: Solution-phase library synthesis and determination of Free–Wilson additivity
  作者：Kelly McClure、Michael Hack、Liming Huang、Clark Sehon、Magda Morton、Lina Li、Terrance D. Barrett、Nigel Shankley、J. Guy Breitenbucher

  DOI：10.1016/j.bmcl.2005.09.048

  日期：2006.1

  High throughput screening revealed compound 1 as a potent antagonist of the CCK1 receptor. Evaluation of the CCK1 SAR in a series of these diarylpyrazole antagonists was conducted in a matrix synthesis format revealing additive (Free-Wilson) and non-additive SAR. This use of additive QSAR modeling in conjunction with combinatorial libraries represents a unique approach to the evaluation of SAR interactions between the variables of any combinatorial matrix. (c) 2005 Elsevier Ltd. All rights reserved.