6-(6-methoxynaphthalen-2-yl)-7H-[1,3]-dioxolo[4,5-f]indol-7-one-5-oxide | 1133205-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-(6-methoxynaphthalen-2-yl)-7H-[1,3]-dioxolo[4,5-f]indol-7-one-5-oxide
• 英文别名: 6-(6-Methoxy-2-naphthyl)-5-oxido-[1,3]dioxolo[4,5-f]indol-5-ium-7-one；6-(6-methoxynaphthalen-2-yl)-5-oxido-[1,3]dioxolo[4,5-f]indol-5-ium-7-one
• CAS: 1133205-03-4
• 化学式: C₂₀H₁₃NO₅
• 分子量: 347.327
• InChiKey: RVMDZQPVWGWQOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 6-(6-methoxynaphthalen-2-yl)-7H-[1,3]-dioxolo[4,5-f]indol-7-one-5-oxide
  参考文献：
  名称：

  Synthesis and Antiplasmodial Activity of New Indolone N-Oxide Derivatives

  摘要：

  A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), its well as for cytotoxic concentration (CC50) on MCF7 and KB human tumor Cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (< 3 nM on FcB1 and = 1.7 nM on 3D7) with a very satisfactory selectivity index (CC50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day.

  DOI：

  10.1021/jm901300d