9-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4,9-dihydrofuro[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: 9-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one
• 英文别名: 9-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4,9-dihydro-3H-furo[3,4-b]quinolin-1-one
• 化学式: C₂₁H₂₁NO₆
• 分子量: 383.401
• InChiKey: NXMWSGRASNWHBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(3,4-dimethoxyphenyl)-2-hydroxymethyl-6,7-dimethoxyquinoline-3-carboxylic acid lactone 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以91%的产率得到9-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4,9-dihydrofuro[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。
• Catalytic one-pot microwave assisted synthesis of 4-azapodophyllotoxin derivatives and rational design of experiment
  作者：Peng Chang、Alexandre Aillerie、Marion Kosmala、Sylvain Pellegrini、Till Bousquet、Muriel Bigan、Lydie Pélinski

  DOI：10.1039/c5nj01785h

  日期：——

  A catalytic one-pot microwave assisted synthesis of 4-azapodophyllotoxin has been described. Rational design of experiment has been used to obtain the reaction yield.

  已经描述了催化的一锅微波辅助合成的4-氮杂鬼臼毒素。实验的合理设计已被用来获得反应产率。
• 4-Aza-2,3-dehydro-4-deoxypodophyllotoxins: simple aza-podophyllotoxin analogues possessing potent cytotoxicity
  作者：Yukio Hitotsuyanagi、Masamoto Fukuyo、Kyoko Tsuda、Masatsugu Kobayashi、Akira Ozeki、Hideji Itokawa、Koichi Takeya

  DOI：10.1016/s0960-894x(99)00693-9

  日期：2000.2

  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.