N1-(7-chloroquinolin-4-yl)-N2-(7α,12α-diacetoxy-5β-cholan-24-amino-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane)-1,2-etandiamine | 1065535-88-7

• 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: N1-(7-chloroquinolin-4-yl)-N2-(7α,12α-diacetoxy-5β-cholan-24-amino-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane)-1,2-etandiamine
• CAS: 1065535-88-7
• 化学式: C₄₅H₆₄ClN₃O₈
• 分子量: 810.471
• InChiKey: IJPCAYMXRVHCDP-DHEAOOPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  57
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  127
• 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-al-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到N1-(7-chloroquinolin-4-yl)-N2-(7α,12α-diacetoxy-5β-cholan-24-amino-3-spiro-6'-(1',2',4',5'-tetraoxacyclohexane)-3'-spirocyclohexane)-1,2-etandiamine
  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.