Ethyl 6-amino-5-cyano-4-(3,4-dimethoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate | 1022149-96-7

• 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: Ethyl 6-amino-5-cyano-4-(3,4-dimethoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
• CAS: 1022149-96-7
• 化学式: C₁₈H₂₁N₃O₄
• 分子量: 343.382
• InChiKey: MXSHZFZSQSCLEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  107
• 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-4-(3,4-dimethoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate 、 环己酮 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以94%的产率得到Ethyl 5-amino-4-(3,4-dimethoxyphenyl)-2-methyl-1,4,6,7,8,9-hexahydrobenzo[b][1,8]naphthyridine-3-carboxylate
  参考文献：
  名称：

  Tacripyrines, the First Tacrine−Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer’s Disease

  摘要：

  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.

  DOI：

  10.1021/jm801292b
• 作为产物：
  描述：

  2-<3,4-Dimethoxy-benzyliden>-acetessigsaeure-aethylester 、 2-氰基乙脒酸乙酯盐酸盐 在 乙酸铵 作用下， 以 甲醇 为溶剂， 反应 0.58h， 以77%的产率得到Ethyl 6-amino-5-cyano-4-(3,4-dimethoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis of 6-amino-1,4-dihydropyridines that prevent calcium overload and neuronal death

  摘要：

  The synthesis and pharmacology of 6-amino-1,4-dihydropyridines, such as ethyl 6-amino-4-aryl-5-cyano-1,4-dihydro-2-methyl-3-pyridinecarboxylic acids (3-16) and 2-amino-4-aryl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinenitriles (17-21) are described. Compounds 18 and 21, at the concentration of 0.3 mu M, proved to be the best blockers of the [Ca2+] overload induced by depolarization with high [K+] of SH-SY5Y neuroblastoma cells, with values of 63.8% and 50.4%, respectively. Most of the compounds induced a remarkable neuroprotective effect against toxicity caused by high [K+]-elicited [Ca2+] overload, and against H2O2-generated free radicals, in SH-SY5Y cells. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.06.001

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。