| 1519728-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• CAS: 1519728-23-4
• 化学式: C₃₃H₄₅N₃O₆
• 分子量: 579.737
• InChiKey: DYRLGYVVLPUPAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  、 磷酸伯氨喹 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Novel Endoperoxide-Based Transmission-Blocking Antimalarials with Liver- and Blood-Schizontocidal Activities

  摘要：

  In a search for effective compounds against both the blood- and liver-stages of infection by malaria parasites with the ability to block the transmission of the disease to mosquito vectors, a series of hybrid compounds combining either a 1,2,4-trioxane or 1,2,4,5-tetraoxane and 8-aminoquinoline moieties were synthesized and screened for their antimalarial activity. These hybrid compounds showed high potency against both exoerythrocytic and erythrocytic forms of malaria parasites, comparable to representative trioxane-based counterparts. Furthermore, they efficiently blocked the development of the sporogonic cycle in the mosquito vector. The tetraoxane-based hybrid 5, containing an amide linker between the two moieties, effectively cleared a patent blood-stage P. berghei infection in mice after i.p. administration. Overall, these results indicate that peroxide-8-aminoquinoline hybrids are excellent starting points to develop an agent that conveys all the desired antimalarial multistage activities in a single chemical entity and, as such, with the potential to be used in malaria elimination campaigns.

  DOI：

  10.1021/ml4002985

文献信息

• Novel Endoperoxide-Based Transmission-Blocking Antimalarials with Liver- and Blood-Schizontocidal Activities
  作者：Daniela Miranda、Rita Capela、Inês S. Albuquerque、Patrícia Meireles、Isa Paiva、Fátima Nogueira、Richard Amewu、Jiri Gut、Philip J. Rosenthal、Rudi Oliveira、Maria M. Mota、Rui Moreira、Francesc Marti、Miguel Prudêncio、Paul M. O’Neill、Francisca Lopes

  DOI：10.1021/ml4002985

  日期：2014.2.13

  In a search for effective compounds against both the blood- and liver-stages of infection by malaria parasites with the ability to block the transmission of the disease to mosquito vectors, a series of hybrid compounds combining either a 1,2,4-trioxane or 1,2,4,5-tetraoxane and 8-aminoquinoline moieties were synthesized and screened for their antimalarial activity. These hybrid compounds showed high potency against both exoerythrocytic and erythrocytic forms of malaria parasites, comparable to representative trioxane-based counterparts. Furthermore, they efficiently blocked the development of the sporogonic cycle in the mosquito vector. The tetraoxane-based hybrid 5, containing an amide linker between the two moieties, effectively cleared a patent blood-stage P. berghei infection in mice after i.p. administration. Overall, these results indicate that peroxide-8-aminoquinoline hybrids are excellent starting points to develop an agent that conveys all the desired antimalarial multistage activities in a single chemical entity and, as such, with the potential to be used in malaria elimination campaigns.