4-chloro-1-(3'-pyrazolylamino)benzo[g]phthalazine | 1263797-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-chloro-1-(3'-pyrazolylamino)benzo[g]phthalazine
• 英文别名: 4-Chloro-1-(3''-pyrazolylamino)benzo[g]phthalazine；4-chloro-N-(1H-pyrazol-5-yl)benzo[g]phthalazin-1-amine
• CAS: 1263797-16-5
• 化学式: C₁₅H₁₀ClN₅
• 分子量: 295.731
• InChiKey: JMVNGIKKZXPWAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氨基吡唑 、 1,4-二氯-苯并[g]二氮杂萘 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以24%的产率得到4-chloro-1-(3'-pyrazolylamino)benzo[g]phthalazine
  参考文献：
  名称：

  In Vivo Trypanosomicidal Activity of Imidazole- or Pyrazole-Based Benzo[g]phthalazine Derivatives against Acute and Chronic Phases of Chagas Disease

  摘要：

  The in vivo trypanosomicidal activity of the imidazole-based benzo[g]phthalazine derivatives 1-4 and of the new related pyrazole-based compounds 5 and 6 has been studied in both the acute and chronic phases of Chagas disease. As a rule, compounds 1-6 were more active and less toxic than benznidazole in the two stages of the disease, and the monosubstituted derivatives 2, 4, and 6 were more effective than their disubstituted analogs. Feasible mechanisms of action of compounds 1-6 against the parasite have been explored by considering their inhibitory effect on the Fe-SOD enzyme, the nature of the excreted metabolites and the ultrastructural alterations produced. A complementary histopathological analysis has confirmed that the monosubstituted derivatives are less toxic than the reference drug, with the behavior of the imidazole-based compound 4 being especially noteworthy.

  DOI：

  10.1021/jm101198k

文献信息

• <i>In Vivo</i> Trypanosomicidal Activity of Imidazole- or Pyrazole-Based Benzo[<i>g</i>]phthalazine Derivatives against Acute and Chronic Phases of Chagas Disease
  作者：Manuel Sánchez-Moreno、Ana M. Sanz、Fernando Gómez-Contreras、Pilar Navarro、Clotilde Marín、Inmaculada Ramírez-Macias、María Jose Rosales、Francisco Olmo、Isabel Garcia-Aranda、Lucrecia Campayo、Carmen Cano、Francisco Arrebola、María J. R. Yunta

  DOI：10.1021/jm101198k

  日期：2011.2.24

  The in vivo trypanosomicidal activity of the imidazole-based benzo[g]phthalazine derivatives 1-4 and of the new related pyrazole-based compounds 5 and 6 has been studied in both the acute and chronic phases of Chagas disease. As a rule, compounds 1-6 were more active and less toxic than benznidazole in the two stages of the disease, and the monosubstituted derivatives 2, 4, and 6 were more effective than their disubstituted analogs. Feasible mechanisms of action of compounds 1-6 against the parasite have been explored by considering their inhibitory effect on the Fe-SOD enzyme, the nature of the excreted metabolites and the ultrastructural alterations produced. A complementary histopathological analysis has confirmed that the monosubstituted derivatives are less toxic than the reference drug, with the behavior of the imidazole-based compound 4 being especially noteworthy.