9-[3,4-dimethoxy-5-(methylsulfanyl)phenyl]-6,9-dihydro[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8(5H)-one | 867070-15-3

• 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-[3,4-dimethoxy-5-(methylsulfanyl)phenyl]-6,9-dihydro[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8(5H)-one
• 英文别名: 8-(3,4-Dimethoxy-5-methylsulfanylphenyl)-5,12,14-trioxa-2-azatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),3(7),9,11(15)-tetraen-6-one
• CAS: 867070-15-3
• 化学式: C₂₁H₁₉NO₆S
• 分子量: 413.451
• InChiKey: VTRGCHNNWCTNQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-羟基-2(5H)-呋喃酮 、 3,4-亚甲二氧基苯胺 、 3,4-dimethoxy-5-(methylthio)benzaldehyde 以70%的产率得到9-[3,4-dimethoxy-5-(methylsulfanyl)phenyl]-6,9-dihydro[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8(5H)-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

文献信息

• Insecticidal heterolignans—Tubuline polymerization inhibitors with activity against chewing pests
  作者：Jens Frackenpohl、Isabelle Adelt、Horst Antonicek、Christian Arnold、Patricia Behrmann、Nicole Blaha、Jutta Böhmer、Oliver Gutbrod、Roman Hanke、Sabine Hohmann、Marc van Houtdreve、Peter Lösel、Olga Malsam、Martin Melchers、Valentina Neufert、Elisabeth Peschel、Udo Reckmann、Thomas Schenke、Hans-Peter Thiesen、Robert Velten、Kathrin Vogelsang、Hans-Christoph Weiss

  DOI：10.1016/j.bmc.2009.01.042

  日期：2009.6

  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.