N-2-[(7-chloroquinolin-4-yl)amino]ethyl-7α,12α-diacetoxy-5β-cholan-24-amido-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane | 1065535-85-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N-2-[(7-chloroquinolin-4-yl)amino]ethyl-7α,12α-diacetoxy-5β-cholan-24-amido-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane
• CAS: 1065535-85-4
• 化学式: C₄₅H₆₂ClN₃O₉
• 分子量: 824.455
• InChiKey: CLXCIKXUTHDGKM-UARFMYFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  58
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-(2-氨基乙基)氨基-7-氯喹啉 、 7α,12α-diacetoxy-5β-cholan-24-oic acid-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane 在 氯甲酸乙酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以80%的产率得到N-2-[(7-chloroquinolin-4-yl)amino]ethyl-7α,12α-diacetoxy-5β-cholan-24-amido-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane
  参考文献：
  名称：

  New Chimeric Antimalarials with 4-Aminoquinoline Moiety Linked to a Tetraoxane Skeleton

  摘要：

  The synthesis of the chimeric molecules consisting of two pharmacophores, tetraoxane and 7-chloro-4-aminoquinoline, is reported. The tetraoxanes 2, 4, and 8 show relatively potent in vitro antimalarial activities, with IC90 values for the Plasmodium falciparum strain W2 of 2.26, 12.44, and 10.74 nM, respectively. In addition, two compounds, 2 and 4, cured mice in a modified Thompson test for antimalarial blood stage activity, with a minimum curative dose of 80 mg/kg, a minimum active dose of 20 mg/kg/day, and a maximum tolerated dose of > 960 mg/kg.

  DOI：

  10.1021/jm8006905

文献信息

• New Chimeric Antimalarials with 4-Aminoquinoline Moiety Linked to a Tetraoxane Skeleton
  作者：Igor Opsenica、Dejan Opsenica、Charlotte Anne Lanteri、Lalaine Anova、Wilbur K. Milhous、Kirsten S. Smith、Bogdan A. Šolaja

  DOI：10.1021/jm8006905

  日期：2008.10.9

  The synthesis of the chimeric molecules consisting of two pharmacophores, tetraoxane and 7-chloro-4-aminoquinoline, is reported. The tetraoxanes 2, 4, and 8 show relatively potent in vitro antimalarial activities, with IC90 values for the Plasmodium falciparum strain W2 of 2.26, 12.44, and 10.74 nM, respectively. In addition, two compounds, 2 and 4, cured mice in a modified Thompson test for antimalarial blood stage activity, with a minimum curative dose of 80 mg/kg, a minimum active dose of 20 mg/kg/day, and a maximum tolerated dose of > 960 mg/kg.