4-((6-(methoxymethoxy)-5-methylnaphthalen-2-yl)carbamoyl)-2-(3-methylbut-2-en-1-yl)phenyl acetate | 1567349-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-((6-(methoxymethoxy)-5-methylnaphthalen-2-yl)carbamoyl)-2-(3-methylbut-2-en-1-yl)phenyl acetate
• CAS: 1567349-64-7
• 化学式: C₂₇H₂₉NO₅
• 分子量: 447.531
• InChiKey: HDJKFSDBPYUQRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-((6-(methoxymethoxy)-5-methylnaphthalen-2-yl)carbamoyl)-2-(3-methylbut-2-en-1-yl)phenyl acetate 在 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到4-((6-hydroxy-5-methylnaphthalen-2-yl)carbamoyl)-2-(3-methylbut-2-en-1-yl)phenyl acetate
  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：

  6-bromo-2-(methoxymethoxy)-1-methylnaphthalene 在 吡啶 、 叠氮基三甲基硅烷 、 C.I.酸性橙108 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 生成 4-((6-(methoxymethoxy)-5-methylnaphthalen-2-yl)carbamoyl)-2-(3-methylbut-2-en-1-yl)phenyl acetate
  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