3-(6-nitro-2,3,4-trimethoxyphenyl)-1-phenylpropanoyl-4,5-dihydro-1H-pyrazole | 1445859-47-1

• 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: 3-(6-nitro-2,3,4-trimethoxyphenyl)-1-phenylpropanoyl-4,5-dihydro-1H-pyrazole
• CAS: 1445859-47-1
• 化学式: C₂₁H₂₃N₃O₆
• 分子量: 413.43
• InChiKey: LPJGTLMRJNFRHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103.5
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-(6-nitro-2,3,4-trimethoxyphenyl)-1-phenylpropanoyl-4,5-dihydro-1H-pyrazole 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以68%的产率得到3-(6-amino-2,3,4-trimethoxyphenyl)-1-phenypropanoyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group

  摘要：

  In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In general, we can confirm that these pyrazoles are nNOS selective inhibitors. In addition, taking these compounds as a reference, we have designed and synthesized a series of new derivatives by modification of the heterocycle in 1-position, and by introduction of electrondonating or electron-withdrawing substituents in the aromatic ring. These derivatives have been evaluated as nNOS and iNOS inhibitors in order to identify new compounds with improved activity and selectivity. Compound 3r, with three methoxy electron-donating groups in the phenyl moiety, is the most potent nNOS inhibitor, showing good selectivity nNOS/iNOS. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.016
• 作为产物：
  描述：

  1-(6-nitro-2,3,4-trimethoxyphenyl)prop-2-en-1-ol 在 Jones reagent 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 6.17h， 生成 3-(6-nitro-2,3,4-trimethoxyphenyl)-1-phenylpropanoyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group

  摘要：

  In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In general, we can confirm that these pyrazoles are nNOS selective inhibitors. In addition, taking these compounds as a reference, we have designed and synthesized a series of new derivatives by modification of the heterocycle in 1-position, and by introduction of electrondonating or electron-withdrawing substituents in the aromatic ring. These derivatives have been evaluated as nNOS and iNOS inhibitors in order to identify new compounds with improved activity and selectivity. Compound 3r, with three methoxy electron-donating groups in the phenyl moiety, is the most potent nNOS inhibitor, showing good selectivity nNOS/iNOS. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.016