ethyl 2,6-di(2-thienyl)-1-phenyl-4-phenylamino-1,2,5,6-tetrahydropyridine-3-carboxylate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 2,6-di(2-thienyl)-1-phenyl-4-phenylamino-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: ethyl 1-phenyl-4-(phenylamino)-2,6-di(thiophen-2-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 4-anilino-1-phenyl-2,6-di(thiophen-2-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate；Ethyl 2,6-di(2-thienyl)-1-phenyl-4-phenylamino-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 4-anilino-1-phenyl-2,6-dithiophen-2-yl-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₂₈H₂₆N₂O₂S₂
• 分子量: 486.659
• InChiKey: BWQFTDFPKWMSGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  98
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 乙酰乙酸乙酯 、 苯胺 在 aluminum potassium sulfate dodecahydrate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以78%的产率得到ethyl 2,6-di(2-thienyl)-1-phenyl-4-phenylamino-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  明矾作为功能化哌啶多组分合成的有效催化剂

  摘要：

  已经报道了在明矾作为有效催化剂的存在下通过苯胺，β-酮酸酯和醛的一锅多组分反应合成官能化哌啶的有效方法。本方法提供了诸如后处理简单，反应时间短的优点，并且提供了快速获得各种官能化哌啶的优点。

  DOI：

  10.1007/s11164-017-2979-3

文献信息

• NO2-Fe(III)PcCl@C -catalyzed one-pot synthesis of tetrahydropyridine derivatives
  作者：Jiao-dan Wang、Qiao-li Lin、Jun Qiu、Xiao-feng Gou、Cheng-wen Hua、Jun-long Zhao、Bang Chen

  DOI：10.1134/s1070363217040259

  日期：2017.4

  efficient, one-pot synthesis of functionalized tetrahydropyridines by multicomponent condensation of ethyl acetoacetate, two equivalents of aromatic aldehyde, and aromatic amine in the presence of a catalytic amount of NO2-Fe(III)PcCl@C is reported. In this way, a series of pharmacologically interesting substituted pyridine derivatives were obtained in moderate to good yields.

  据报道，在催化量的NO 2 -Fe（III）PcCl @ C存在下，通过乙酰乙酸乙酯，两当量的芳族醛和芳族胺的多组分缩合，高效，一锅法合成官能化的四氢吡啶。以这种方式，以中等至良好的产率获得了一系列药理学上有趣的取代吡啶衍生物。
• Multicomponent synthesis and antimicrobial activity of alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-tetrahydropyridine-3-carboxylates
  作者：A. N. Yankin、N. V. Nosova、V. L. Gein、M. V. Tomilov

  DOI：10.1134/s1070363215040131

  日期：2015.4

  Reaction of arylamines with aromatic aldehydes and beta-ketoesters in the presence of bismuth nitrate or crystalline iodine as a catalyst afforded to alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-tetrahydropyridine-3-carboxy-lates. Antimicrobial activity of the obtained compounds was studied.
• Highly functionalized tetrahydropyridines are cytotoxic and selective inhibitors of human puromycin sensitive aminopeptidase
  作者：Raghunath Aeluri、Roopa Jones Ganji、Anil Kumar Marapaka、Vijaykumar Pillalamarri、Manjula Alla、Anthony Addlagatta

  DOI：10.1016/j.ejmech.2015.10.026

  日期：2015.12

  Efficient one-pot five-component synthetic protocols for highly functionalized tetrahydropyridines (THPs) and their biological evaluation have been illustrated. Synthesis of novel functionalized tetrahydropyridines containing differential substitutions at 2,6-positions has been achieved via a modified MCR. Cytotoxic studies of 23 synthesized compounds have been carried out against three different cell lines, namely A-549, HeLa and HepG2, wherein some compounds have displayed appreciable cytotoxicity. Further, investigation of enzyme inhibition by the synthesized THPs has been carried out against four members of M1 family aminopeptidases. Several compounds have selectively inhibited only one member of this enzyme family i.e., human puromycin sensitive aminopeptidase (hPSA). Among the compounds; 4h, 9b, 9e and 10a demonstrated best inhibition against hPSA. (C) 2015 Elsevier Masson SAS. All rights reserved.