aurachin E | 113366-10-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: aurachin E
• 英文别名: 11-Methyl-10-(3,7,11-trimethyldodeca-2,6,10-trienyl)-1,3-diazatricyclo[6.3.1.04,12]dodeca-4,6,8(12),10-tetraene-2,9-dione；11-methyl-10-(3,7,11-trimethyldodeca-2,6,10-trienyl)-1,3-diazatricyclo[6.3.1.04,12]dodeca-4,6,8(12),10-tetraene-2,9-dione
• CAS: 113366-10-2
• 化学式: C₂₆H₃₂N₂O₂
• 分子量: 404.552
• InChiKey: CQZZUPSXBXLXRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴化氰 、 1-羟基-2-甲基-3-[(2E,6E)-3,7,11-三甲基十二碳-2,6,10-三烯基]喹啉-4-酮 以 二氯甲烷 为溶剂， 反应 0.5h， 以37%的产率得到3-bromocarbonylamino-2-methyl-1H-quinoline-4-one
  参考文献：
  名称：

  Semisynthesis and Antiplasmodial Activity of the Quinoline Alkaloid Aurachin E

  摘要：

  A one-step synthesis of the rare aurachin E (1) from the easily accessible aurachin C (2) and cyanogen bromide is described. 3-Bromocarbamoylquinoline (5) is formed in a side reaction with concomitant loss of the 3-farnesyl residue. In an alternative approach, aurachin D (3) was reacted with phosgene and sodium azide to form the imidazolone ring of 1 via N-acylation. Unexpectedly, the initial reaction occurred at the carbonyl group of 3 to give 1H-pyrrolo[3,2-c]quinoline 4. The reaction sequence represents a novel route to this type of compound. Aurachin E, contrary to other aurachins, combines a high in vitro antiplasmodial activity with low cytotoxicity and absence of mitochondrial respiratory inhibition.

  DOI：

  10.1021/np8004612

文献信息

• Semisynthesis and Antiplasmodial Activity of the Quinoline Alkaloid Aurachin E
  作者：Gerhard Höfle、Bettina Böhlendorf、Thomas Fecker、Florenz Sasse、Brigitte Kunze

  DOI：10.1021/np8004612

  日期：2008.12.1

  A one-step synthesis of the rare aurachin E (1) from the easily accessible aurachin C (2) and cyanogen bromide is described. 3-Bromocarbamoylquinoline (5) is formed in a side reaction with concomitant loss of the 3-farnesyl residue. In an alternative approach, aurachin D (3) was reacted with phosgene and sodium azide to form the imidazolone ring of 1 via N-acylation. Unexpectedly, the initial reaction occurred at the carbonyl group of 3 to give 1H-pyrrolo[3,2-c]quinoline 4. The reaction sequence represents a novel route to this type of compound. Aurachin E, contrary to other aurachins, combines a high in vitro antiplasmodial activity with low cytotoxicity and absence of mitochondrial respiratory inhibition.