N-(1-Naphthalenylmethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-6-ethanamine | 945495-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1-Naphthalenylmethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-6-ethanamine
• 英文别名: N-(naphthalen-1-ylmethyl)-2-(3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl)ethanamine
• CAS: 945495-78-3
• 化学式: C₂₄H₃₁N₅
• 分子量: 389.544
• InChiKey: VZTHJOQCORJUSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(1-Naphthalenylmethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-6-ethanamine 在 sodium perchlorate 、 水 作用下， 生成
  参考文献：
  名称：

  A thermodynamic insight into the recognition of hydrophilic and hydrophobic amino acids in pure water by aza-scorpiand type receptors

  摘要：

  在水中关于蝎烯和氮杂大环与氨基酸相互作用的热力学研究表明，熵驱动的稳定化通常与溶解/脱溶过程相关。

  DOI：

  10.1039/c4ob02092h
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 生成 N-(1-Naphthalenylmethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-6-ethanamine
  参考文献：
  名称：

  Scorpiand-like azamacrocycles prevent the chronic establishment of Trypanosoma cruzi in a murine model

  摘要：

  Chagas disease is today one of the most important neglected diseases for its upcoming expansion to nonendemic areas and has become a threat to blood recipients in many countries. In this study, the trypanocidal activity of ten derivatives of a family of aza-scorpiand like macrocycles is evaluated against Thypanosoma cruzi in vitro and in vivo murine model in which the acute and chronic phases of Chagas disease were analyzed. The compounds 4, 3 and 1 were found to be more active against the parasite and less toxic against Vero cells than the reference drug benznidazole, 4 being the most active compound, particularly in the chronic phase. While all these compounds showed a remarkable degree of inhibition of the Fe-SOD enzyme of the epimastigote forms of T cruzi, they produced a negligible inhibition of human CuZn-SOD and Mn-SOD from Escherichia coli. The modifications observed by H-1 NMR and the amounts of excreted catabolites by the parasites after treatment suggested that the mechanism of action could be based on interactions of the side chains of the compounds with enzymes of the parasite metabolism. The ultrastructural alterations observed in treated epimastigote forms confirmed that the compounds having the highest activity are those causing the largest cell damage. A complementary histopathological analysis confirmed that the compounds tested were significantly less toxic to mammals than the reference drug. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.048

文献信息

• Hydrogen and Copper Ion Induced Molecular Reorganizations in Two New Scorpiand-Like Ligands Appended with Pyridine Rings
  作者：Salvador Blasco、Begoña Verdejo、M. Paz Clares、Carmen E. Castillo、Andrés G. Algarra、Julio Latorre、M. Angeles Máñez、Manuel G. Basallote、Conxa Soriano、Enrique García-España

  DOI：10.1021/ic100609h

  日期：2010.8.2

  kinetic studies of complex formation and decomposition. For L1, those processes occur in a single kinetic step, whereas for L2 they occur with the formation of a detectable reaction intermediate whose structure corresponds to that resulting from the movement typical of scorpiands. Another interesting conclusion derived from kinetic studies on complex formation is that the reactive form of the ligand

  由三（2-氨基乙基）胺部分组成的两个新配体的合成，这些配体通过亚甲基连接到吡啶间隔基的2,6位，其中悬臂进一步被2-苯甲基（L1）或3-官能化提出了pycolyl（L2）基团。L1和L2的质子化和Cu 2+的形成已经使用电位，NMR，X射线和动力学实验研究了配合物。结果提供了有关这种所谓的蝎蝎配体化学中分子运动相关性的新信息。仅在取代基在臂上的位置不同的这两个配体之间的比较揭示了热力学和动力学性质上的重要差异。具有L1的Cu 2+络合物比具有L2的Cu 2+络合物更稳定几个数量级，这肯定是因为在后一种情况下，悬臂上的吡啶氮无法与配体为六齿的配体与金属离子配位，这可能是因为在[Cu L1 ] 2+的情况下发生，如其晶体结构所示。在复合物形成和分解的动力学研究中，两个配体之间也发现了显着差异。对于L1而言，这些过程是在单个动力学步骤中发生的，而对于L2而言，它们是通过形成可检测的反应中间体而发
• A thermodynamic insight into the recognition of hydrophilic and hydrophobic amino acids in pure water by aza-scorpiand type receptors
  作者：Salvador Blasco、Begoña Verdejo、Carla Bazzicalupi、Antonio Bianchi、Claudia Giorgi、Concepción Soriano、Enrique García-España

  DOI：10.1039/c4ob02092h

  日期：——

  Thermodynamic studies about the interaction of scorpiand aza-macrocycles with amino acids in water show entropy driven stabilisations often associated with solvation/desolvation processes.

  在水中关于蝎烯和氮杂大环与氨基酸相互作用的热力学研究表明，熵驱动的稳定化通常与溶解/脱溶过程相关。
• Scorpiand-like azamacrocycles prevent the chronic establishment of Trypanosoma cruzi in a murine model
  作者：Francisco Olmo、Clotilde Marín、M. Paz Clares、Salvador Blasco、M. Teresa Albelda、Conxa Soriano、Ramón Gutiérrez-Sánchez、Francisco Arrebola-Vargas、Enrique García-España、Manuel Sánchez-Moreno

  DOI：10.1016/j.ejmech.2013.09.048

  日期：2013.12

  Chagas disease is today one of the most important neglected diseases for its upcoming expansion to nonendemic areas and has become a threat to blood recipients in many countries. In this study, the trypanocidal activity of ten derivatives of a family of aza-scorpiand like macrocycles is evaluated against Thypanosoma cruzi in vitro and in vivo murine model in which the acute and chronic phases of Chagas disease were analyzed. The compounds 4, 3 and 1 were found to be more active against the parasite and less toxic against Vero cells than the reference drug benznidazole, 4 being the most active compound, particularly in the chronic phase. While all these compounds showed a remarkable degree of inhibition of the Fe-SOD enzyme of the epimastigote forms of T cruzi, they produced a negligible inhibition of human CuZn-SOD and Mn-SOD from Escherichia coli. The modifications observed by H-1 NMR and the amounts of excreted catabolites by the parasites after treatment suggested that the mechanism of action could be based on interactions of the side chains of the compounds with enzymes of the parasite metabolism. The ultrastructural alterations observed in treated epimastigote forms confirmed that the compounds having the highest activity are those causing the largest cell damage. A complementary histopathological analysis confirmed that the compounds tested were significantly less toxic to mammals than the reference drug. (C) 2013 Elsevier Masson SAS. All rights reserved.