5-methoxycanthin-4-one

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吲哚萘啶生物碱
• 英文名称: 5-methoxycanthin-4-one
• 英文别名: drymaritin；4H-Indolo[3,2,1-de][1,5]naphthyridin-4-one, 5-methoxy-；3-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-2,5,7,9(16),10,12,14-heptaen-4-one
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: ARKHSSXCCQCKAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Bredereck 试剂 、 2-甲氧基-1-(9h-吡啶并[3,4-b]吲哚-1-基)-乙酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以97%的产率得到5-methoxycanthin-4-one
  参考文献：
  名称：

  Revised Structure of the Alkaloid Drymaritin

  摘要：

  In 2004, a new anti-HIV alkaloid named drymaritin was isolated from Drymaria diandra. The authors identified the alkaloid as 5-methoxycanthin-4-one on the basis of spectroscopic data. Here we describe a synthetic approach that unambiguously gave 5-methoxycanthin-4-one, but the synthetic product showed spectroscopic data significantly different from those of the Drymaria alkaloid. Extensive re-evaluation of the spectroscopic data published for this and related alkaloids has led to the conclusion that drymaritin does not have a canthin-4-one backbone, but is identical to the known alkaloid cordatanine (4-methoxycanthin-6-one).

  DOI：

  10.1021/np900515b