5-chloro-7-methoxy-2H-pyrano[2,3-b]quinolin-2-one | 1133793-38-0

• 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: 5-chloro-7-methoxy-2H-pyrano[2,3-b]quinolin-2-one
• 英文别名: 5-Chloro-7-methoxypyrano[2,3-b]quinolin-2-one
• CAS: 1133793-38-0
• 化学式: C₁₃H₈ClNO₃
• 分子量: 261.664
• InChiKey: CNXXEDUEBPWXNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-7-methoxy-2H-pyrano[2,3-b]quinolin-2-one 、 4-甲磺酰胺基苯胺 以 N,N-二甲基甲酰胺 为溶剂， 以10%的产率得到N-[4-(7'-methoxy-2'-oxo-2H-pyrano[2,3-b]quinolin-5'-ylamino)phenyl]methanesulfonamide
  参考文献：
  名称：

  Synthesis and antitumor activity of novel amsacrine analogs: The critical role of the acridine moiety in determining their biological activity

  摘要：

  A new series of N-[4-(2'-oxo-2H-pyrano[2,3-b]quinolin-5'-ylamino)-phenyl]-methanesulfonamides was prepared and analyzed as novel amsacrine-like derivatives. Our preliminary biological evaluation has shown that the replacement of the acridine moiety with the analogous 2-oxo-2H-pyrano[2,3-b]quinoline system drastically reduced both their anticancer activity and their propency to intercalate into double stranded DNA. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.072
• 作为产物：
  描述：

  ethyl 3-(4'-chloro-6'-methoxy-2'-oxoquinolin-3'-yl)-acrylate 在 PPA 作用下， 反应 2.0h， 以21%的产率得到5-chloro-7-methoxy-2H-pyrano[2,3-b]quinolin-2-one
  参考文献：
  名称：

  Synthesis and antitumor activity of novel amsacrine analogs: The critical role of the acridine moiety in determining their biological activity

  摘要：

  A new series of N-[4-(2'-oxo-2H-pyrano[2,3-b]quinolin-5'-ylamino)-phenyl]-methanesulfonamides was prepared and analyzed as novel amsacrine-like derivatives. Our preliminary biological evaluation has shown that the replacement of the acridine moiety with the analogous 2-oxo-2H-pyrano[2,3-b]quinoline system drastically reduced both their anticancer activity and their propency to intercalate into double stranded DNA. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.072

文献信息

• Synthesis and antitumor activity of novel amsacrine analogs: The critical role of the acridine moiety in determining their biological activity
  作者：Adriana Chilin、Giovanni Marzaro、Christine Marzano、Lisa Dalla Via、Maria Grazia Ferlin、Giovanni Pastorini、Adriano Guiotto

  DOI：10.1016/j.bmc.2008.11.072

  日期：2009.1

  A new series of N-[4-(2'-oxo-2H-pyrano[2,3-b]quinolin-5'-ylamino)-phenyl]-methanesulfonamides was prepared and analyzed as novel amsacrine-like derivatives. Our preliminary biological evaluation has shown that the replacement of the acridine moiety with the analogous 2-oxo-2H-pyrano[2,3-b]quinoline system drastically reduced both their anticancer activity and their propency to intercalate into double stranded DNA. (C) 2008 Elsevier Ltd. All rights reserved.