ethyl 1-phenyl-4-(phenylamino)-2,6-di(pyridin-3-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1130970-02-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 1-phenyl-4-(phenylamino)-2,6-di(pyridin-3-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: ethyl 1'-phenyl-4'-(phenylamino)-1',2',5',6'-tetrahydro-[2,2':6',2''-terpyridine]-3'-carboxylate；ethyl 1-phenyl-4-(phenylamino)-2,6-bis(pyridin-3-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 4-anilino-1-phenyl-2,6-dipyridin-3-yl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1130970-02-3
• 化学式: C₃₀H₂₈N₄O₂
• 分子量: 476.578
• InChiKey: VHNNWENYRZGOLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-phenyl-4-(phenylamino)-2,6-di(pyridin-3-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以60%的产率得到1-phenyl-2,6-di(pyridin-3-yl)-1,2,3,6-tetrahydropyridin-4-ol
  参考文献：
  名称：

  Highly functionalized tetrahydropyridines are cytotoxic and selective inhibitors of human puromycin sensitive aminopeptidase

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.10.026
• 作为产物：
  描述：

  3-吡啶甲醛 、 乙酰乙酸乙酯 、 苯胺 在 氯化锆(IV) 作用下， 以 乙醇 为溶剂， 生成 ethyl 1-phenyl-4-(phenylamino)-2,6-di(pyridin-3-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Highly functionalized tetrahydropyridines are cytotoxic and selective inhibitors of human puromycin sensitive aminopeptidase

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.10.026

文献信息

• Organocatalyzed highly atom economic one pot synthesis of tetrahydropyridines as antimalarials
  作者：Mridul Misra、Swaroop Kumar Pandey、Vivek Parashar Pandey、Jyoti Pandey、Renu Tripathi、Rama Pati Tripathi

  DOI：10.1016/j.bmc.2008.11.062

  日期：2009.1

  A highly atom economic one pot synthesis of tetrahydropyridines was achieved by L-proline/TFA catalysed multicomponent reaction of beta-keto-esters, aromatic aldehydes and anilines. The synthesized compounds were screened against Plasmodium falciparum in vitro and one of them showed antimalarial activity with MIC as low as 0.09 mu g/mL. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.