Echinatin | 34221-41-5

• 物质功能分类: 天然产物 - 查尔酮类化合物
• 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: Echinatin
• 英文别名: 2′-methoxy-4′,4-dihydroxychalcone；4,4'-dihydroxy-2-methoxychalcone；3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 34221-41-5
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: QJKMIJNRNRLQSS-UHFFFAOYSA-N

物化性质

• 熔点：
  210°C (dec.)
• 沸点：
  509.8±50.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  DMSO：250 mg/mL（924.97 mM；需要超声波）

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2914509090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

制备方法与用途

生物活性方面，Echinatin是从中草药甘草中分离得到的一种查尔酮，具有保肝和抗炎作用。在水溶液中，Echinatin 经过电子转移 (ET) 和质子转移 (PT) 过程表现出抗氧化作用。在大鼠实验中，该物质可以被快速吸收和消除，其绝对生物利用度约为 6.81%。

化学性质方面，Echinatin是一种白色结晶粉末，可溶于甲醇、乙醇、DMSO 等有机溶剂，并来源于甘草根。

用途上，刺甘草查尔酮不仅具有抗肿瘤和保肝抗炎作用，还适用于含量测定、鉴定及药理实验等研究。

反应信息

• 作为反应物：
  描述：

  Echinatin 、 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39.1%的产率得到3-[2-methoxy-4-(oxiran-2-ylmethoxy)phenyl]-1-[4-(oxiran-2-ylmethoxy)phenyl]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：

  3-(2-methoxy-4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-1-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one 在 盐酸 、 水 作用下， 生成 Echinatin
  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