N-(4-methoxybenzylidene)pyridin-3-amine | 40037-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methoxybenzylidene)pyridin-3-amine
• 英文别名: 1-(4-methoxyphenyl)-N-pyridin-3-ylmethanimine
• CAS: 40037-15-8
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: LDYXXIIIECCHCF-UHFFFAOYSA-N

物化性质

• 沸点：
  361.2±22.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzylidene)pyridin-3-amine 、 茚 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成
  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 、 4-甲氧基苯甲醛 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(4-methoxybenzylidene)pyridin-3-amine
  参考文献：
  名称：

  N-取代氨基酸酯的新型四组分合成

  摘要：

  使用固相结合的有机异氰化物合成 N 取代的氨基酸酯库，为最终分子提供 Cl 合成子。这种新型的四组分一锅反应以可接受的收率提供最终产物，粗反应产物纯度高，有助于最终纯化。异氰基树脂的制备也描述了由 ATR 光谱控制的中间体。

  DOI：

  10.1055/s-2002-34864

文献信息

• A Novel Four-Component Synthesis of<i>N</i>-Substituted Amino Acid Esters
  作者：Bernd Henkel、Lutz Weber

  DOI：10.1055/s-2002-34864

  日期：——

  A library of N-substituted amino acid esters was synthesized using a solid phase bound organic isocyanide that provides a Cl synthon to the final molecule. This novel four-component, one-pot reaction delivers the final products in acceptable yields with high purities of the crude reaction products, facilitating the final purification. The preparation of the isocyano resin is also described the intermediates

  使用固相结合的有机异氰化物合成 N 取代的氨基酸酯库，为最终分子提供 Cl 合成子。这种新型的四组分一锅反应以可接受的收率提供最终产物，粗反应产物纯度高，有助于最终纯化。异氰基树脂的制备也描述了由 ATR 光谱控制的中间体。
• Metal–organic frameworks incorporating azobenzene-based ligands as a heterogeneous Lewis-acid catalyst for cyanosilylation of imines
  作者：Aasim Saeed、Xiao-Yu Zhang、Zi-Qing Huang、Xin-Yang Zhao、Lei Xu、Yue Zhao、Wei-Yin Sun、Jing Zhao

  DOI：10.1039/d2ra06858c

  日期：——

  Cd(ii). The Zn(ii) cations in 1 adopted a distorted seesaw coordination geometry and the coordination between Zn(ii) and organic linkers gave two-dimensional (2D) coordination networks, while the Cd(ii) cations in 2 could also bind with the carboxylate groups from neighboring coordination networks to form a three-dimensional (3D) coordination framework. Furthermore, complexes 1 and 2 showed high catalytic

  本工作通过偶氮苯基配体与Zn(NO3)2/CdCO3在溶剂热条件下反应合成了两种新型金属有机骨架(MOF)，其分子式为[Zn2(abtc)(azpy)(H2O) 2]·4H2O} n (1) 和 [Cd(abtc)0.5(azpy)0.5(H2O)]·3H2O} n (2) (H4abtc = 3,3',5,5'-偶氮苯四甲酸，azpy = 4,4'-偶氮二吡啶）。根据单晶X射线衍射(SC-XRD)分析，配合物1和2具有非常相似的结构，除了由于Zn(ii)和Cd的阳离子半径不同而导致的中心金属节点的配位模式之外。 (二). 1 中的 Zn(ii) 阳离子采用扭曲的跷跷板配位几何形状，Zn(ii) 和有机连接基之间的配位形成二维 (2D) 配位网络，而 2 中的 Cd(ii) 阳离子也可以与羧酸盐结合相邻协调网络中的群体形成三维（3D）协调框架。此外，配合物1和2作为非均相路易斯酸催化剂
• Antileishmanial effect of new indeno-1,5-naphthyridines, selective inhibitors of Leishmania infantum type IB DNA topoisomerase
  作者：Ana Tejería、Yolanda Pérez-Pertejo、Rosa M. Reguera、Rafael Balaña-Fouce、Concepción Alonso、María Fuertes、María González、Gloria Rubiales、Francisco Palacios

  DOI：10.1016/j.ejmech.2016.09.017

  日期：2016.11

  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.