13,26-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazapentacyclo[22.2.1.1(11,14).0(2,6).0(15,19)]octacosa-1(27),9,11,14(28),22,24-hexaene | 244217-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 13,26-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazapentacyclo[22.2.1.1(11,14).0(2,6).0(15,19)]octacosa-1(27),9,11,14(28),22,24-hexaene
• 英文别名: 13,26-Dibenzyl-3,6,9,12,13,16,19,22,25,26-decazapentacyclo[22.2.1.111,14.02,6.015,19]octacosa-1(27),9,11,14(28),22,24-hexaene
• CAS: 244217-88-7
• 化学式: C₃₂H₃₈N₁₀
• 分子量: 562.721
• InChiKey: OBYUXNXREZNVTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  13,26-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazapentacyclo[22.2.1.1(11,14).0(2,6).0(15,19)]octacosa-1(27),9,11,14(28),22,24-hexaene 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以83%的产率得到13,26-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1^11,14]-octacosa-1(27),11,14(28),24-tetraene
  参考文献：
  名称：

  In Vitro and in Vivo Trypanosomicidal Activity of Pyrazole-Containing Macrocyclic and Macrobicyclic Polyamines: Their Action on Acute and Chronic Phases of Chagas Disease

  摘要：

  The in vitro and in vivo anti-Trypanosoma cruzi activity of the pyrazole-containing macrobicyclic polyamine 1 and N-methyl- and N-benzyl-substituted monocyclic polyamines 2 and 3 was studied. Activity against both the acute and chronic phases of Chagas disease was considered. The compounds were more active against the parasite and less toxic against Vero cells than the reference drug benznidazole, but 1 and 2 were especially effective, where cryptand 1 was the most active, particularly in the chronic phase. The activity results found for these compounds were complemented and discussed by considering their inhibitory effect on the iron superoxide dismutase enzyme of the parasite, the nature of the metabolites excreted after treatment, and the ultrastructural alterations produced. A complementary histopathological analysis confirmed that the compounds tested were significantly less toxic to mammals than the reference drug and that 1 and 2 exhibited lower levels of damage than 3.

  DOI：

  10.1021/jm2017144
• 作为产物：
  描述：

  二乙烯三胺 、 1-benzyl-3,5-pyrazoledicarbaldehyde 以 乙腈 为溶剂， 以55%的产率得到13,26-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazapentacyclo[22.2.1.1(11,14).0(2,6).0(15,19)]octacosa-1(27),9,11,14(28),22,24-hexaene
  参考文献：
  名称：

  In Vitro and in Vivo Trypanosomicidal Activity of Pyrazole-Containing Macrocyclic and Macrobicyclic Polyamines: Their Action on Acute and Chronic Phases of Chagas Disease

  摘要：

  The in vitro and in vivo anti-Trypanosoma cruzi activity of the pyrazole-containing macrobicyclic polyamine 1 and N-methyl- and N-benzyl-substituted monocyclic polyamines 2 and 3 was studied. Activity against both the acute and chronic phases of Chagas disease was considered. The compounds were more active against the parasite and less toxic against Vero cells than the reference drug benznidazole, but 1 and 2 were especially effective, where cryptand 1 was the most active, particularly in the chronic phase. The activity results found for these compounds were complemented and discussed by considering their inhibitory effect on the iron superoxide dismutase enzyme of the parasite, the nature of the metabolites excreted after treatment, and the ultrastructural alterations produced. A complementary histopathological analysis confirmed that the compounds tested were significantly less toxic to mammals than the reference drug and that 1 and 2 exhibited lower levels of damage than 3.

  DOI：

  10.1021/jm2017144

文献信息

• In Vitro and in Vivo Trypanosomicidal Activity of Pyrazole-Containing Macrocyclic and Macrobicyclic Polyamines: Their Action on Acute and Chronic Phases of Chagas Disease
  作者：Manuel Sánchez-Moreno、Clotilde Marín、Pilar Navarro、Laurent Lamarque、Enrique García-España、Carlos Miranda、Oscar Huertas、Francisco Olmo、Fernando Gómez-Contreras、Javier Pitarch、Francisco Arrebola

  DOI：10.1021/jm2017144

  日期：2012.5.10

  The in vitro and in vivo anti-Trypanosoma cruzi activity of the pyrazole-containing macrobicyclic polyamine 1 and N-methyl- and N-benzyl-substituted monocyclic polyamines 2 and 3 was studied. Activity against both the acute and chronic phases of Chagas disease was considered. The compounds were more active against the parasite and less toxic against Vero cells than the reference drug benznidazole, but 1 and 2 were especially effective, where cryptand 1 was the most active, particularly in the chronic phase. The activity results found for these compounds were complemented and discussed by considering their inhibitory effect on the iron superoxide dismutase enzyme of the parasite, the nature of the metabolites excreted after treatment, and the ultrastructural alterations produced. A complementary histopathological analysis confirmed that the compounds tested were significantly less toxic to mammals than the reference drug and that 1 and 2 exhibited lower levels of damage than 3.