3-(4-methoxy-phenyl)-1-(4-oxiranylmethoxy-phenyl)-propenone | 19532-83-3

• 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: 3-(4-methoxy-phenyl)-1-(4-oxiranylmethoxy-phenyl)-propenone
• 英文别名: 4'-(2,3-Epoxy-propoxy)-4-methoxy-chalcone；3-(4-methoxyphenyl)-1-[4-(oxiran-2-ylmethoxy)phenyl]prop-2-en-1-one
• CAS: 19532-83-3
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: XLPRGKCOGCXGTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxy-phenyl)-1-(4-oxiranylmethoxy-phenyl)-propenone 在 盐酸 、 水 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以76.2%的产率得到1-[4-(3-chloro-2-hydroxypropoxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and topoisomerase II inhibitory and cytotoxic activity of oxiranylmethoxy- and thiiranylmethoxy-chalcone derivatives

  摘要：

  In order to find potential anticancer drug candidate targeting topoisomerases enzyme, we have designed and synthesized oxiranylmethoxy- and thiiranylmethoxy-retrochalcone derivatives and evaluated their pharmacological activity including topoisomerases inhibitory and cytotoxic activity. Of the compounds prepared compound 25 showed comparable or better cytotoxic activity against cancer cell lines tested. Compound 25 inhibited MCF7 (IC50: 0.49 +/- 0.21 mu M) and HCT15 (IC50: 0.23 +/- 0.02 mu M) carcinoma cell growth more efficiently than references. In the topoisomerases inhibition test, all the compounds were inactive to topoisomerase I but moderate inhibitors to topoisomerase II enzyme. Especially, compound 25 inhibited topoisomerase II activity with comparable extent to etoposide at 100 mu M concentrations. Correlation between cytotoxicity and topoisomerase II inhibitory activity implies that compound 25 can be a possible lead compound for anticancer drug impeding the topoisomerase II function. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.037
• 作为产物：
  描述：

  4'-hydroxy-4-methoxychalcone 、 环氧氯丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 以74.6%的产率得到3-(4-methoxy-phenyl)-1-(4-oxiranylmethoxy-phenyl)-propenone
  参考文献：
  名称：

  Synthesis and topoisomerase II inhibitory and cytotoxic activity of oxiranylmethoxy- and thiiranylmethoxy-chalcone derivatives

  摘要：

  In order to find potential anticancer drug candidate targeting topoisomerases enzyme, we have designed and synthesized oxiranylmethoxy- and thiiranylmethoxy-retrochalcone derivatives and evaluated their pharmacological activity including topoisomerases inhibitory and cytotoxic activity. Of the compounds prepared compound 25 showed comparable or better cytotoxic activity against cancer cell lines tested. Compound 25 inhibited MCF7 (IC50: 0.49 +/- 0.21 mu M) and HCT15 (IC50: 0.23 +/- 0.02 mu M) carcinoma cell growth more efficiently than references. In the topoisomerases inhibition test, all the compounds were inactive to topoisomerase I but moderate inhibitors to topoisomerase II enzyme. Especially, compound 25 inhibited topoisomerase II activity with comparable extent to etoposide at 100 mu M concentrations. Correlation between cytotoxicity and topoisomerase II inhibitory activity implies that compound 25 can be a possible lead compound for anticancer drug impeding the topoisomerase II function. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.037
• 作为试剂：
  描述：

  3,4-Dimethoxy-4'-[2-hydroxy-3-(4-phenylpiperazin-1-yl)-propoxy]-chalcone 、 甲醇 在 3-(4-methoxy-phenyl)-1-(4-oxiranylmethoxy-phenyl)-propenone 作用下， 以compound 23 was obtained from 4′-(2,3-epoxy-propoxy)-4-methoxy-chalcone, 13 (1 g, 3.2 mmol) and iso-propyl amine (1.36 mL, 16 mmol) in dry methanol (100 mL)的产率得到4'-[2-Hydroxy-3-iso-propylamino-propoxy]-4-methoxy-chalcone
  参考文献：
  名称：

  Oxy substituted chalcones as antihyperglycemic and antidyslipidemic agents

  摘要：

  本发明提供了适当取代的查尔酮，例如，如下所示的结构式所代表的：其中R1、R2和R3选自H、OH、O-烷基、O-苯基和O-取代苯基的群；B代表Ar-Z-O或RO；其中Z是具有最多5个碳原子的烷基；R是取代的丙醇胺，其中取代的氨基基团选自叔丁基、正丁基、异丁基、异丙基、4-苯基哌嗪-1-基、4-(2-甲氧基苯基)-哌嗪-1-基和3,4-二甲氧基苯乙基；而Ar是噻唑烷二酮亚甲基苯氧基。制备的化合物已被证明在各种动物模型中具有显著的降糖作用，表明具有进一步开发的潜力。

  公开号：

  US07807712B2