| 1608463-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• CAS: 1608463-54-2
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: BEMGBFGOCBEHDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  68.37
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 咪唑 、 甲醇 、 三氟化硼乙醚 、 四丁基氟化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.67h， 生成 N-(7-(((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-8-methyl-2-phenethoxyquinolin-3-yl)-4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of coumarin replacements of novobiocin as Hsp90 inhibitors

  摘要：

  Since Hsp90 modulates all six hallmarks of cancer simultaneously, it has become an attractive target for the development of cancer chemotherapeutics. In an effort to develop more efficacious compounds for Hsp90 inhibition, novobiocin analogues were prepared by replacing the central coumarin core with naphthalene, quinolinone, and quinoline surrogates. These modifications allowed for modification of the 2-position, which was previously unexplored. Biological evaluation of these compounds suggests a hydrophobic pocket about the 2-position of novobiocin. Anti-proliferative activities of these analogues against multiple cancer cell lines identified 2-alkoxyquinoline derivatives to exhibit improved activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.056
• 作为产物：
  描述：

  2-甲基-3-硝基苯酚 在 吡啶 、 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 叠氮基三甲基硅烷 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 C.I.酸性橙108 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 氯苯 、 丙酮 为溶剂， 反应 61.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of coumarin replacements of novobiocin as Hsp90 inhibitors

  摘要：

  Since Hsp90 modulates all six hallmarks of cancer simultaneously, it has become an attractive target for the development of cancer chemotherapeutics. In an effort to develop more efficacious compounds for Hsp90 inhibition, novobiocin analogues were prepared by replacing the central coumarin core with naphthalene, quinolinone, and quinoline surrogates. These modifications allowed for modification of the 2-position, which was previously unexplored. Biological evaluation of these compounds suggests a hydrophobic pocket about the 2-position of novobiocin. Anti-proliferative activities of these analogues against multiple cancer cell lines identified 2-alkoxyquinoline derivatives to exhibit improved activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.056