ethyl 1,4-dihydro-2-methyl-4-(4-nitrophenyl)-6-phenyl-3-pyridinecarboxylate | 113293-80-4

• 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 1,4-dihydro-2-methyl-4-(4-nitrophenyl)-6-phenyl-3-pyridinecarboxylate
• 英文别名: ethyl 2-methyl-4-(4-nitrophenyl)-6-phenyl-1,4-dihydropyridine-3-carboxylate
• CAS: 113293-80-4
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: YYVSBISRUIKORF-UHFFFAOYSA-N

物化性质

• 沸点：
  547.8±50.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 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：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1,4-dihydro-2-methyl-4-(4-nitrophenyl)-6-phenyl-3-pyridinecarboxylate 在 manganese(IV) oxide 、 氢氧化钾 、 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 2-Methyl-4-(4-nitro-phenyl)-6-phenyl-nicotinoyl chloride
  参考文献：
  名称：

  Studies on Cerebral Protective Agents. IV. Synthesis of Novel 4-Arylpyridine and 4-Arylpyridazine Derivatives with Anti-anoxic Activity.

  摘要：

  在寻找新的脑保护剂的过程中，合成了一系列具有氨基基团在吡啶（或吡嗪）环C-3位的4-(3或4-硝基苯基)-6-苯基吡啶（或吡嗪）和2-(3-硝基苯基)-6-苯基吡啶，通过相应的新型1,4-二氢衍生物合成，并在小鼠中测试其抗缺氧（AA）活性。四种化合物（2c、2f、3a、4a）在32 mg/kg的腹腔注射剂量下表现出显著的AA活性。这些结果表明，吡啶（或吡嗪）环C-3位与含氮碱性基团之间的四原子连接似乎也是表达AA活性的先决条件。

  DOI：

  10.1248/cpb.41.156
• 作为产物：
  描述：

  (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one 生成 ethyl 1,4-dihydro-2-methyl-4-(4-nitrophenyl)-6-phenyl-3-pyridinecarboxylate
  参考文献：
  名称：

  Morpholine containing pyridine compounds, compositions and use

  摘要：

  一种含氮杂环化合物，化学式为：##STR1##其中R.sup.1是较低的烷基，可选择地取代为羟基、卤素或杂环基，羧基、酯化羧基、羰基取代的羰基，可选择地取代为杂环(较低)烷基或较低烷基氨基(较低)烷基的含氮杂环羰基，可选择地取代为较低烷基的含氮杂环羰基，或可选择地取代为较低烷基氨基(较低)烷基的脲基，R.sup.3是氢或卤素；R.sup.2是取代硝基的苯基，X是.dbd.N--或##STR2##其中R.sup.4是较低的烷基或卤代(较低)烷基，或与R.sup.1共同形成可选择地取代为氧代和较低烷基氨基(较低)烷基的含氮杂环基；或R.sup.2是较低烷基，X是##STR3##其中R.sup.4是取代硝基的苯基；以及其药学上可接受的盐，其制备方法和包含相同的药物(例如抗高血压)组合物。

  公开号：

  US04857527A1

文献信息

• N-containing heterocyclic compounds, processes for the preparation thereof and composition comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0228845A2

  公开（公告）日：1987-07-15

  An N-containing heterocyclic compound of the formula: I wherein R' is lower alkyl optionally substituted with hydroxy, halogen or a heterocyciic group, carboxy, esterified carboxy, carbamoyl optionally substituted with heterocyclic(lower)alkyl or lower alkylamino(lower)alkyl, N-containing heterocycliccarbonyl optionally substituted with lower alkyl, or ureido optionally substituted with lower alkylamino(lower)alkyl, and R3 is hydrogen or halogen; R2 is phenyl substituted with nitro, and X is = N-or in which R' is lower alkyl or halo (lower) alkyl, or is taken together with R' to form an N-containing heterocyclic group optionally substituted with oxo and lower alkylamino(lower)alkyl; or R2 is lower alkyl, and X is in which R4 is phenyl substituted with nitro; and a pharmaceutically acceptable salt thereof, processes for the preparation thereof and composition comprising the same.

  式中的含 N 杂环化合物：I 其中 R'是任选被羟基、卤素或杂环基取代的低级烷基、羧基、酯化羧基、任选被杂环（低级）烷基或低级烷基氨基（低级）烷基取代的氨基甲酰基、任选被低级烷基取代的含 N 杂环羰基或任选被低级烷基氨基（低级）烷基取代的脲基，以及 R3 是氢或卤素； R2 是被硝基取代的苯基，以及 X 是 = N-or 其中 R'是低级烷基或卤代（低级）烷基，或与 R'一起形成可选被氧代和低级烷基氨基（低级）烷基取代的含 N 杂环基团；或 R2 是低级烷基，且 X 是 其中 R4 是被硝基取代的苯基； 及其药学上可接受的盐、制备工艺和包含这些成分的组合物。
• 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.
• US4831030A
  申请人：——

  公开号：US4831030A

  公开（公告）日：1989-05-16
• US4857527A
  申请人：——

  公开号：US4857527A

  公开（公告）日：1989-08-15
• US4931453A
  申请人：——

  公开号：US4931453A

  公开（公告）日：1990-06-05