2-amino-4-(3-fluorophenyl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile | 697233-59-3

• 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: 2-amino-4-(3-fluorophenyl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile
• 英文别名: 2-amino-4-(3-fluorophenyl)-6-methyl-5-oxo-4H-pyrano[3,2-c]quinoline-3-carbonitrile
• CAS: 697233-59-3
• 化学式: C₂₀H₁₄FN₃O₂
• 分子量: 347.348
• InChiKey: PIZOUDFQBDSZCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 丙二腈 、 3-氟苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以90%的产率得到2-amino-4-(3-fluorophenyl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile
  参考文献：
  名称：

  Structural Simplification of Bioactive Natural Products with Multicomponent Synthesis. 2. Antiproliferative and Antitubulin Activities of Pyrano[3,2-c]pyridones and Pyrano[3,2-c]quinolones

  摘要：

  Pyrano[3,2-c]pyridone and pyrano[3,2-c]quinolone structural motifs are commonly found in alkaloids manifesting diverse biological activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed compound libraries based on these privileged heterocyclic scaffolds. The selected library members display low nanomolar antiproliferative activity and induce apoptosis in human cancer cell lines. Mechanistic studies reveal that these compounds induce cell cycle arrest in the G2/M phase and block in vitro tubulin polymerization. Because of the successful clinical use of microtubule-targeting agents, these heterocyclic libraries are expected to provide promising new leads in anticancer drug design.

  DOI：

  10.1021/jm701499n

文献信息

• Pyrano [3,2-C] Pyridones and Related Heterocyclic Compounds as Pharmaceutical Agents for Treating Disorders Responsive to Apoptosis, Antiproliferation or Vascular Disruption, and the Use Thereof
  申请人：Kornienko Alexander

  公开号：US20090247566A1

  公开（公告）日：2009-10-01

  A pharmaceutical composition comprising a pharmaceutically acceptable excipient or carrier and a compound Formula I: or a pharmaceutically acceptable salt or prodrug thereof.

  一种药物组合物，包含药用可接受的辅料或载体和化合物公式I:或其药用可接受的盐或前药。
• US8349864B2
  申请人：——

  公开号：US8349864B2

  公开（公告）日：2013-01-08
• Structural Simplification of Bioactive Natural Products with Multicomponent Synthesis. 2. Antiproliferative and Antitubulin Activities of Pyrano[3,2-<i>c</i>]pyridones and Pyrano[3,2-<i>c</i>]quinolones
  作者：Igor V. Magedov、Madhuri Manpadi、Marcia A. Ogasawara、Adriana S. Dhawan、Snezna Rogelj、Severine Van slambrouck、Wim F. A. Steelant、Nikolai M. Evdokimov、Pavel Y. Uglinskii、Eerik M. Elias、Erica J. Knee、Paul Tongwa、Mikhail Yu. Antipin、Alexander Kornienko

  DOI：10.1021/jm701499n

  日期：2008.4.1

  Pyrano[3,2-c]pyridone and pyrano[3,2-c]quinolone structural motifs are commonly found in alkaloids manifesting diverse biological activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed compound libraries based on these privileged heterocyclic scaffolds. The selected library members display low nanomolar antiproliferative activity and induce apoptosis in human cancer cell lines. Mechanistic studies reveal that these compounds induce cell cycle arrest in the G2/M phase and block in vitro tubulin polymerization. Because of the successful clinical use of microtubule-targeting agents, these heterocyclic libraries are expected to provide promising new leads in anticancer drug design.