ethyl 6-amino-5-cyano-2-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

• 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-amino-5-cyano-2-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
• 化学式: C₁₆H₁₆N₄O₄
• 分子量: 328.327
• InChiKey: QUTJZASPLFHOMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 6-amino-5-cyano-2-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 、 环己酮 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.5h， 以95%的产率得到5-Amino-2-methyl-4-(2-nitro-phenyl)-1,4,6,7,8,9-hexahydro-benzo[b][1,8]naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Novel Multipotent Tacrine−Dihydropyridine Hybrids with Improved Acetylcholinesterase Inhibitory and Neuroprotective Activities as Potential Drugs for the Treatment of Alzheimer's Disease

  摘要：

  In this work we describe the synthesis and biological evaluation of the tacrine-1,4-dihydropyridine (DHP) hybrids (3-11). These multipotent molecules are the result of the juxtaposition of an acetylcholinesterase inhibitor (AChEI) such as tacrine (1) and a 1,4-DHP such as nimodipine (2). Compounds 3-11 are very selective and potent AChEIs and show an excellent neuprotective profile and a moderate Ca2+ channel blockade effect. Consequently, these molecules are new potential drugs for the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm061047j
• 作为产物：
  描述：

  2-(2-nitrobenzylidene)malononitrile 、 乙酰乙酸乙酯 在 ammonium acetate 作用下， 反应 0.25h， 生成 ethyl 6-amino-5-cyano-2-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  1,4-二氢吡啶衍生物在无溶剂研磨条件下的合成

  摘要：

  这篇文章已被撤回。

  DOI：

  10.1080/00397911.2010.499488

文献信息

• Organic base grafted on magnetic nanoparticles as a recoverable catalyst for the green synthesis of hydropyridine rings
  作者：Mohammad Ali Bodaghifard

  DOI：10.1007/s13738-019-01788-y

  日期：2020.2

  Synthesis of 4-aminiquinaldine grafted on silica-coated nano-Fe3O4 particles (MNPs-AQ) and their performance as a retrievable heterogeneous basic catalyst are disclosed. The catalytic performance of this novel material was studied for the green synthesis of substituted 1,4-dihydropyridine and polyhydroquinoline derivatives via one-pot multicomponent reactions. Eco-friendly method, high yield and purity

  二氧化硅包覆的纳米Fe 3 O 4接枝的4-aminiquinaldaldine的合成公开了颗粒（MNPs-AQ）及其作为可回收的非均相碱性催化剂的性能。研究了这种新型材料的催化性能，用于通过一锅多组分反应绿色合成取代的1,4-二氢吡啶和聚氢喹啉衍生物。环保的方法，所需产品的高收率和纯度以及较短的反应时间以及后处理程序的简便性概述了这些新方法相对于早期方法的优势。通过TEM，SEM，XRD，EDS和FT-IR分析技术对核/壳杂化纳米颗粒的表面和磁性进行了表征。该纳米催化剂是可再循环的，其催化活性没有任何降低。
• Bis(4-pyridylamino)triazine-stabilized magnetite nanoparticles: preparation, characterization and application as a retrievable catalyst for the green synthesis of 4<i>H</i>-pyran, 4<i>H</i>-thiopyran and 1,4-dihydropyridine derivatives
  作者：M. A. Bodaghifard、A. Mobinikhaledi、S. Asadbegi

  DOI：10.1002/aoc.3557

  日期：2017.2

  Synthesis of bis(4‐pyridylamino)triazine stabilized on silica‐coated nano‐Fe3O4 particles, and their feasibility as a reusable heterogeneous basic catalyst are reported. The catalytic performance of this novel material was studied for the green synthesis of highly functionalized 4H‐pyran, 4H‐thiopyran and 1,4‐dihydropyridine derivatives via one‐pot multicomponent reactions. Eco‐friendly method, high

  已报道了在二氧化硅包覆的纳米Fe 3 O 4颗粒上稳定的双（4-吡啶基氨基）三嗪的合成及其作为可重复使用的非均相碱性催化剂的可行性。研究了这种新型材料的催化性能，用于绿色合成高度官能化的4 H-吡喃，4 H一锅多组分反应生成的硫代吡喃和1,4-二氢吡啶衍生物。环保的方法，所需产品的高收率和纯度，较短的反应时间以及简便的后处理程序概述了这些新方法相对于早期方法的优势。通过透射和扫描电子显微镜，X射线衍射，能量色散X射线和傅立叶变换红外光谱以及振动样品磁强分析对核-壳杂化纳米颗粒的表面和磁性进行了表征。版权所有©2016 John Wiley＆Sons，Ltd.
• Novel Multipotent Tacrine−Dihydropyridine Hybrids with Improved Acetylcholinesterase Inhibitory and Neuroprotective Activities as Potential Drugs for the Treatment of Alzheimer's Disease
  作者：José Marco-Contelles、Rafael León、Cristóbal de los Ríos、Antonio Guglietta、José Terencio、Manuela G. López、Antonio G. García、Mercedes Villarroya

  DOI：10.1021/jm061047j

  日期：2006.12.1

  In this work we describe the synthesis and biological evaluation of the tacrine-1,4-dihydropyridine (DHP) hybrids (3-11). These multipotent molecules are the result of the juxtaposition of an acetylcholinesterase inhibitor (AChEI) such as tacrine (1) and a 1,4-DHP such as nimodipine (2). Compounds 3-11 are very selective and potent AChEIs and show an excellent neuprotective profile and a moderate Ca2+ channel blockade effect. Consequently, these molecules are new potential drugs for the treatment of Alzheimer's disease.
• Synthesis of 1,4-Dihydropyridine Derivatives Under Solvent-Free and Grinding Conditions
  作者：Adeleh Moshtaghi Zonouz、Davoud Moghani

  DOI：10.1080/00397911.2010.499488

  日期：2011.7.15

  This article has been retracted.

  这篇文章已被撤回。
• Tacripyrines, the First Tacrine−Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer’s Disease
  作者：José Marco-Contelles、Rafael León、Cristóbal de los Ríos、Abdelouahid Samadi、Manuela Bartolini、Vincenza Andrisano、Oscar Huertas、Xavier Barril、F. Javier Luque、María I. Rodríguez-Franco、Beatriz López、Manuela G. López、Antonio G. García、María do Carmo Carreiras、Mercedes Villarroya

  DOI：10.1021/jm801292b

  日期：2009.5.14

  Tacripyrines (1-14) have been designed by combining an ACNE inhibitor (tacrine) with a calcium antagonist such as nimodipine and are targeted to develop a multitarget therapeutic strategy to confront AD. Tacripyrines are selective and potent ACNE inhibitors in the nanomolar range. The mixed type inhibition of hAChE activity of compound 11 (IC50 105 +/- 15 nM) is associated to a 30.7 +/- 8.6% inhibition of the proaggregating action of ACNE on the A beta and a moderate inhibition of A beta self-aggregation (34.9 +/- 5.4%). Molecular modeling indicates that binding of compound 11 to the ACNE PAS mainly involves the (R)-11 enantiomer, which also agrees with the noncompetitive inhibition mechanism exhibited by p-methoxytacripyrine 11. Tacripyrines are neuroprotective agents, show moderate Ca2+ channel blocking effect, and cross the blood-brain barrier, emerging as lead candidates for treating AD.