4,9-dihydro-6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)furo[3,4-b]quinolin-1(3H)-one

• 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: 4,9-dihydro-6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)furo[3,4-b]quinolin-1(3H)-one
• 英文别名: 6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one；6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)-4,9-dihydro-3H-furo[3,4-b]quinolin-1-one
• 化学式: C₂₂H₂₃NO₇
• 分子量: 413.427
• InChiKey: CGYIMMFMENAHSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)furo[3,4-b]quinolin-1(3H)-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以84%的产率得到4,9-dihydro-6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)furo[3,4-b]quinolin-1(3H)-one
  参考文献：
  名称：

  4-Aza-2,3-dehydro-4-deoxypodophyllotoxins: simple aza-podophyllotoxin analogues possessing potent cytotoxicity

  摘要：

  4-Aza-2,3-dehydro-4-deoxypodophyllotoxin analogues 3a-n were synthesized through quinolines 2a-n. Comparison of their cytotoxicity against P-388 leukemia cells revealed that the steric effects of the ring B substituents on the activity are greater than the electronic effects, while the presence of a methoxy group on the ring E is not essential to exhibit potent cytotoxicity. Analogues 3a and 3b proved to be more than twice as cytotoxic as natural podophyllotoxin (1). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00693-9

文献信息

• Synthesis and antibacterial activity of new lactone 1,4-dihydroquinoline derivatives
  作者：Rosangela S. Laurentiz、Willian P. Gomes、Ana P. R. Pissurno、Fernanda A. Santos、Vinicius Cristian O. Santos、Carlos H. G. Martins

  DOI：10.1007/s00044-017-2129-x

  日期：2018.4

  and 4ci displayed moderate antibacterial activity against P. gingivalis. 4bi was the most active compound against the three strains of Mycobacterium. Based on structure–activity relationship studies, we observed that the presence of a nitro group on the benzylic ring and a methylenedioxy group on the dihydroquinoline ring enhanced the antibacterial activity of the derivatives.

  在这项工作中，有效地合成了一系列内酯1,4-二氢喹啉衍生物4并通过1 H和13 C NMR进行了表征。评价了所合成的化合物对细菌菌株牙龈卟啉单胞菌，黑线菌，血链球菌和血链球菌以及对结核分枝杆菌，鸟分枝杆菌和堪萨斯分枝杆菌的体外抗菌活性。结果表明，所评价的化合物对革兰氏阴性细菌更具活性。化合物4ba，4bb，4BG，4bi，40亿，4CH，和4 Cl显示温和的抗菌活性对牙龈卟啉菌。4bi是对三种分枝杆菌最具活性的化合物。根据结构-活性关系研究，我们观察到苄基环上存在硝基，二氢喹啉环上存在亚甲基二氧基，可以增强衍生物的抗菌活性。
• 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.
• A Multicomponent Reaction for the One-Pot Synthesis of 4-Aza-2,3-didehydropodophyllotoxin and Derivatives
  作者：Christophe Tratrat、Sylviane Giorgi-Renault、Henri-Philippe Husson

  DOI：10.1021/ol0200908

  日期：2002.9.1

  A convergent method has been found to prepare 4-aza-2,3-didehydropodophyllotoxin and derivatives in a one-pot procedure. The mechanism of the reaction between tetronic acid, anilines, and benzaldehydes is discussed.
• US6548515B1
  申请人：——

  公开号：US6548515B1

  公开（公告）日：2003-04-15