9-(3,5-dimethoxyphenyl)-6-(phenoxy)-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one | 867069-43-0

• 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)-6-(phenoxy)-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one
• 英文别名: 9-(3,5-dimethoxyphenyl)-6-phenoxy-4,9-dihydro-3H-furo[3,4-b]quinolin-1-one
• CAS: 867069-43-0
• 化学式: C₂₅H₂₁NO₅
• 分子量: 415.445
• InChiKey: HFZDGFSMMHRITH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基-2(5H)-呋喃酮 、 3,5-二甲氧基苯甲醛 、 3-苯氧基苯胺 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 3.0h， 以9%的产率得到9-(3,5-dimethoxyphenyl)-6-(phenoxy)-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-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.