(E)-1-(2,4-bis(allyloxy)-5-chlorophenyl)-3-(3,4-bis(allyloxy)phenyl)prop-2-en-1-one | 1522361-72-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(2,4-bis(allyloxy)-5-chlorophenyl)-3-(3,4-bis(allyloxy)phenyl)prop-2-en-1-one
• 英文别名: (E)-3-[3,4-bis(prop-2-enoxy)phenyl]-1-[5-chloro-2,4-bis(prop-2-enoxy)phenyl]prop-2-en-1-one
• CAS: 1522361-72-3
• 化学式: C₂₇H₂₇ClO₅
• 分子量: 466.961
• InChiKey: FLASLIREIWJUTE-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(2,4-bis(allyloxy)-5-chlorophenyl)-3-(3,4-bis(allyloxy)phenyl)prop-2-en-1-one 在 trans-bis(triphenylphosphine)palladium dichloride 、 甲酸铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以24%的产率得到(E)-1-(5-chloro-2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Discovery of hybrid Hsp90 inhibitors and their anti-neoplastic effects against gefitinib-resistant non-small cell lung cancer (NSCLC)

  摘要：

  Heat shock protein 90 (Hsp90) represents an attractive cancer therapeutic target due to its role in the stabilization and maturation of many oncogenic proteins. We have designed a series of hybrid Hsp90 inhibitors by connecting the resorcinol ring of VER-49009 (2) and the trimethoxyphenyl ring of PU3 (3) using structure-based approach. Subsequent testing established that compound 1f inhibited gefitinib-resistant H1975 cell proliferation, brought about the degradation of Hsp90 client proteins including EGFR, Met, Her2 and Akt and induced the expression of Hsp70. The design, synthesis, and evaluation of 1f are described herein. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.034
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 氯化亚砜 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 70.0h， 生成 (E)-1-(2,4-bis(allyloxy)-5-chlorophenyl)-3-(3,4-bis(allyloxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Discovery of hybrid Hsp90 inhibitors and their anti-neoplastic effects against gefitinib-resistant non-small cell lung cancer (NSCLC)

  摘要：

  Heat shock protein 90 (Hsp90) represents an attractive cancer therapeutic target due to its role in the stabilization and maturation of many oncogenic proteins. We have designed a series of hybrid Hsp90 inhibitors by connecting the resorcinol ring of VER-49009 (2) and the trimethoxyphenyl ring of PU3 (3) using structure-based approach. Subsequent testing established that compound 1f inhibited gefitinib-resistant H1975 cell proliferation, brought about the degradation of Hsp90 client proteins including EGFR, Met, Her2 and Akt and induced the expression of Hsp70. The design, synthesis, and evaluation of 1f are described herein. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.034