3-Methoxy-benzofuro<3,2-c>chinolin-6(5H)-on | 106636-00-4

• 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: 3-Methoxy-benzofuro<3,2-c>chinolin-6(5H)-on
• 英文别名: 3-methoxy-5H-[1]benzofuro[3,2-c]quinolin-6-one
• CAS: 106636-00-4
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: AURJZPMVZYMYOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基-7-甲氧基-3-苯基喹啉-2(1H)-酮 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 反应 48.0h， 以32%的产率得到3-Methoxy-benzofuro<3,2-c>chinolin-6(5H)-on
  参考文献：
  名称：

  Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives

  摘要：

  Certain indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones 4a,b, 6, 8, 16a-c and 6-anilinoindoloquinoline derivatives 10a,b, 11a,b, 12a,b have been synthesized and evaluated in vitro against a 3-cell lines panel consisting of MCF7 (Breast), NCI-H460 (Lung), and SF-268 (CNS). Those active compounds 4a,b, 6, 8, 10a,b, 11a,b, 12a,b were then evaluated in the full panel of 60 human tumor cell lines derived from nine cancer cell types. The results have shown that cytotoxicity decreases in the order of 6-anilinoindoloquinolines>indoloquinolin-2(1H)-ones>pyrroloquinolin-2(1H)-ones>benzofuroquinolin-2(1H)-ones. Among them, 1-[3-(11H-indolo[3,2-c]quinolin-6ylamino)phenyl]ethanone oxime hydrochloride (14a) and its 2-chloro derivative (11b) were most active, with mean GI(50) values of 1.70 and 1.35 muM, respectively. Both compounds 11a,b were also found to inhibit the growth of SNB-75 (CNS cancer cell) with a GI(50) value of less than 0.01 muM, and, therefore, were selected for further evaluation for in vivo antitumor activity. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(02)00111-6

文献信息

• Synthese von kondensierten Benzofuranen durch Dehydratisierung cyclischer Phenyl-?-Dicarbonylverbindungen
  作者：Thomas Kappe、Alexander Brandner、Wolfgang Stadlbauer

  DOI：10.1007/bf00811290

  日期：1987.10
• KAPPE, THOMAS;BRANDNER, ALEXANDER;STADLBAUER, WOLFGANG, MONATSH. CHEM., 118,(1987) N 10, 1177-1184
  作者：KAPPE, THOMAS、BRANDNER, ALEXANDER、STADLBAUER, WOLFGANG

  DOI：——

  日期：——