(1E)-N-(3-吡啶基)乙烷亚胺 | 596813-59-1

• 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
• 中文名称: (1E)-N-(3-吡啶基)乙烷亚胺
• 英文名称: N-pyridin-3-ylethanimine
• CAS: 596813-59-1
• 化学式: C₇H₈N₂
• 分子量: 120.154
• InChiKey: GHDVZCZPGIGEIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E)-N-(3-吡啶基)乙烷亚胺 、 茚 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 6.0h， 生成 6-methyl-7H-indeno[2,1-c][1,5]naphthyridine
  参考文献：
  名称：

  Antileishmanial effect of new indeno-1,5-naphthyridines, selective inhibitors of Leishmania infantum type IB DNA topoisomerase

  摘要：

  Visceral leishmaniasis is a neglected disease of poor and developing countries. The current therapeutic approach is based on pentavalent antimonial (Sb-V) drugs and amphotericin B, both nephrotoxic and parenterally administered drugs. Therefore, there is a real need of new antileishmanial drugs. Eukaryotic type I DNA topoisomerases (TopIB) have been identified as druggable targets against leishmaniasis. These enzymes are involved in solving topological problems generated during replication, transcription and recombination of DNA. Leishmanial TopIB is a unique heterodimeric protein structurally different than that found in the mammalian host, thus making it an interesting target for drug discovery. Tetrahydro indeno-1,5-naphthyridines 5 and indeno[1,5]naphthyridines 6 were synthesized. The inhibition of Leishmania and human TopIB of these polycyclic heterocycles were studied and their antileishmanial activity on promastigotes and amastigote-infected splenocytes of Leishmania infantum were evaluated. In this regard, it is noteworthy that some of the prepared heterocycles, as compounds 6b, 6i and 5 h, showed selective inhibition of LtopIB while no inhibition of hToplB was observed at evaluated conditions. In addition, the cytotoxic effects of newly synthesized compounds were assessed on host murine splenocytes in order to calculate the corresponding selective indexes (SI). Tetrahydro indeno-1,5-naphthyridines 5e and 5h showed good antileishmanial activity (IC50 values of 0.67 +/- 0.06 and 0.54 +/- 0.17 mu M) with similar activity than the standard drug amphotericin B (0.32 +/- 0.05 mu M) and even tetrahydro indeno-1,5-naphthyridine 5h showed higher (SI) towards L. Infantum amastigotes. Likewise, in the family of indeno-[1,5]-naphthyridines 6, compound 6b showed good antileishmanial activity (IC50 value 0.74 +/- 0.08 mu M) and higher selective index (SI) towards L Infantum amastigotes than amphotericin B. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.017
• 作为产物：
  描述：

  3-氨基吡啶 、 乙醛 以 氯仿 为溶剂， 反应 3.0h， 生成 (1E)-N-(3-吡啶基)乙烷亚胺
  参考文献：
  名称：

  N-(3-吡啶基)醛亚胺的路易斯酸活化氮杂-狄尔斯-阿尔德反应：实验和计算研究

  摘要：

  Povarov 型环加成反应的理论和实验结合研究表明，这是一种异步协同过程，有利于用 BF 3· Et 2 O 进行双路易斯酸活化；在 N-(3-吡啶基)醛亚胺与苯乙烯、环戊二烯或茚之间的反应中观察到内选择性，并以区域和立体选择性方式获得取代的四氢-1,5-萘啶衍生物。

  DOI：

  10.1002/ejoc.200901325