ethyl 6-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate | 1271735-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 6-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
• 英文别名: ethyl 6-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydro-3-pyridinecarboxylate；Ethyl 6-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
• CAS: 1271735-74-0
• 化学式: C₂₁H₂₀ClNO₂
• 分子量: 353.848
• InChiKey: BWRLTXMPYHAFDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4'-chlorochalcone 在 ammonium cerium (IV) nitrate 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以71%的产率得到ethyl 6-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Identification of 4,6-diaryl-1,4-dihydropyridines as a new class of neuroprotective agents

  摘要：

  合成了一系列4,6-二芳基-1,4-二氢吡啶的化合物，采用了一种由氨基乙酸、β-二酮化合物和多种α,β-不饱和酮（包括查尔克酮、其烯基衍生物和杂环类药物）组成的、由CAN催化的与汉茨赫相关的三组分反应。这些化合物缺乏所需的血管活性结构特征，发现能够防止钙过载并表现出神经保护作用。其中一种在C-4位上带有2-噻吩基取代基的化合物显示出最高的神经保护活性，同时也是一种中等强度的抗氧化剂，是该领域进一步研究的良好先导化合物。

  DOI：

  10.1039/c3md20345j

文献信息

• Identification of 4,6-diaryl-1,4-dihydropyridines as a new class of neuroprotective agents
  作者：Giammarco Tenti、Javier Egea、Mercedes Villarroya、Rafael León、José Carlos Fernández、Juan Fernando Padín、Vellaisamy Sridharan、Ma Teresa Ramos、J. Carlos Menéndez

  DOI：10.1039/c3md20345j

  日期：——

  A library of 4,6-diaryl-1,4-dihydropyridines was synthesized using a CAN-catalyzed, Hantzsch-related three component reaction starting from ammonium acetate, β-dicarbonyl compounds and a variety of α,β-unsaturated ketones including chalcones, their vinylogs and heteroanalogues. These compounds lack the structural features needed for vascular activity and were found to prevent calcium overload and behave as neuroprotective agents. One of the compounds, bearing a 2-thienyl substituent at C-4, showed the highest neuroprotective activity and was also a moderate antioxidant, being a good lead compound for further studies in this area.

  合成了一系列4,6-二芳基-1,4-二氢吡啶的化合物，采用了一种由氨基乙酸、β-二酮化合物和多种α,β-不饱和酮（包括查尔克酮、其烯基衍生物和杂环类药物）组成的、由CAN催化的与汉茨赫相关的三组分反应。这些化合物缺乏所需的血管活性结构特征，发现能够防止钙过载并表现出神经保护作用。其中一种在C-4位上带有2-噻吩基取代基的化合物显示出最高的神经保护活性，同时也是一种中等强度的抗氧化剂，是该领域进一步研究的良好先导化合物。
• Cellulose sulfuric acid catalyzed multicomponent reaction for efficient synthesis of 1,4-dihydropyridines via unsymmetrical Hantzsch reaction in aqueous media
  作者：Javad Safari、Sayed Hossein Banitaba、Shiva D. Khalili

  DOI：10.1016/j.molcata.2010.11.012

  日期：2011.2

  C-5-unsubstituted 1,4-dihydropyridines were obtained in good to excellent yields by proceeding through a simple, mild and efficient procedure utilizing cellulose sulfuric acid (CSA) as a catalyst. The reaction work-up is very simple and catalyst can be easily separated from reaction mixture and reused several times in subsequent reactions. (C) 2010 Elsevier B.V. All rights reserved.
• New 5-Unsubstituted Dihydropyridines with Improved Ca_V1.3 Selectivity as Potential Neuroprotective Agents against Ischemic Injury
  作者：Giammarco Tenti、Esther Parada、Rafael León、Javier Egea、Sonia Martínez-Revelles、Ana María Briones、Vellaisamy Sridharan、Manuela G. López、María Teresa Ramos、J. Carlos Menéndez

  DOI：10.1021/jm500263v

  日期：2014.5.22

  C-5-unsubstituted-C-6-aryl-1,4-dihydropyridines were prepared by a CAN-catalyzed multicomponent reaction from chalcones, beta-dicarbonyl compounds, and ammonium acetate. These compounds were able to block Ca2+ entry after a depolarizing stimulus and showed an improved Ca(V)1.3/ Ca(V)1.2 selectivity in comparison with nifedipine. Furthermore, they were able to protect neuroblastoma cells against Ca2+ overload and oxidative stress models. Their selectivity ratio makes them highly interesting for the treatment of neurological disorders where Ca2+ dyshomeostasis and high levels of oxidative stress have been demonstrated. Furthermore, their low potency toward the cardiovascular channel subtype makes them safer by reducing their probable side effects, in comparison to classical 1,4-dihydropyridines. Some compounds afforded good protective profile in a postincubation model that simulates the real clinical situation of ictus patients, offering a therapeutic window of opportunity of great interest for patient recovery after a brain ischemic episode. Good activities were also found in acute ischemia/reperfusion models of oxygen and glucose deprivation.