9-(3,5-dimethoxyphenyl)-5,6,7,9-tetrahydro-8H-[1,3]dioxolo[4,5-g]pyrrolo[3,4-b]-quinolin-8-one | 1175700-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-(3,5-dimethoxyphenyl)-5,6,7,9-tetrahydro-8H-[1,3]dioxolo[4,5-g]pyrrolo[3,4-b]-quinolin-8-one
• 英文别名: 8-(3,5-Dimethoxyphenyl)-12,14-dioxa-2,5-diazatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),3(7),9,11(15)-tetraen-6-one
• CAS: 1175700-21-6
• 化学式: C₂₀H₁₈N₂O₅
• 分子量: 366.373
• InChiKey: XCRKSPBKKOOBEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl 9-(3,5-dimethoxyphenyl)-8-oxo-5,6,8,9-tetrahydro-7H-[1,3]dioxolo[4,5-g]pyrrolo[3,4-b]quinoline-7-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以80%的产率得到9-(3,5-dimethoxyphenyl)-5,6,7,9-tetrahydro-8H-[1,3]dioxolo[4,5-g]pyrrolo[3,4-b]-quinolin-8-one
  参考文献：
  名称：

  Insecticidal heterolignans—Tubuline polymerization inhibitors with activity against chewing pests

  摘要：

  Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.042