7,8-diacetoxy-4-dodecylsulfanylmethyl-2-oxo-2H-1-benzopyran | 1000513-86-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7,8-diacetoxy-4-dodecylsulfanylmethyl-2-oxo-2H-1-benzopyran
• 英文别名: [8-Acetyloxy-4-(dodecylsulfanylmethyl)-2-oxochromen-7-yl] acetate
• CAS: 1000513-86-9
• 化学式: C₂₆H₃₆O₆S
• 分子量: 476.634
• InChiKey: UXTWSDAMVCRJOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  600.1±55.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-chloromethyl-7,8-diacetoxy<1>benzopyran-2(H)-one 、 十二硫醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以38.8%的产率得到7,8-diacetoxy-4-dodecylsulfanylmethyl-2-oxo-2H-1-benzopyran
  参考文献：
  名称：

  Synthesis and protective effects of coumarin derivatives against oxidative stress induced by doxorubicin

  摘要：

  The use of doxorubicin (DOX) in the treatment of solid tumors is limited by cardiotoxicity essentially due to oxidative stress generation. The aim of this study was to identify coumarin derivatives displaying a protective antioxidant activity without affecting DOX antitumoral efficiency. A set of eighteen coumarinic derivatives was synthesized. Their antioxidant power was evaluated in vitro with the FRAP (ferric reducing ability of plasma) method and in human breast adenocarcinoma MCF7 cells using H,DCFDA (2',7'-dichlorodihydrofluorescein diacetate) in a cytometric analysis. 4-Methyl-7,8-dihydroxycoumarin was found to exhibit an important antioxidant strength, a low cytotoxicity, and could decrease ROS (reactive oxygen species) production generated by DOX treatment without affecting DOX cytotoxicity in MCF7 cells. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.004

文献信息

• Synthesis and protective effects of coumarin derivatives against oxidative stress induced by doxorubicin
  作者：Adeline Beillerot、Juan-Carlos Rodríguez Domínguez、Gilbert Kirsch、Denyse Bagrel

  DOI：10.1016/j.bmcl.2007.12.004

  日期：2008.2

  The use of doxorubicin (DOX) in the treatment of solid tumors is limited by cardiotoxicity essentially due to oxidative stress generation. The aim of this study was to identify coumarin derivatives displaying a protective antioxidant activity without affecting DOX antitumoral efficiency. A set of eighteen coumarinic derivatives was synthesized. Their antioxidant power was evaluated in vitro with the FRAP (ferric reducing ability of plasma) method and in human breast adenocarcinoma MCF7 cells using H,DCFDA (2',7'-dichlorodihydrofluorescein diacetate) in a cytometric analysis. 4-Methyl-7,8-dihydroxycoumarin was found to exhibit an important antioxidant strength, a low cytotoxicity, and could decrease ROS (reactive oxygen species) production generated by DOX treatment without affecting DOX cytotoxicity in MCF7 cells. (C) 2007 Elsevier Ltd. All rights reserved.