S-2-(3,4-diacetoxyphenyl)ethyl ethanethioate | 1415490-07-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: S-2-(3,4-diacetoxyphenyl)ethyl ethanethioate
• 英文别名: [2-Acetyloxy-4-(2-acetylsulfanylethyl)phenyl] acetate
• CAS: 1415490-07-1
• 化学式: C₁₄H₁₆O₅S
• 分子量: 296.344
• InChiKey: DQQOSAPGVMJTQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  95
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-2-(3,4-diacetoxyphenyl)ethyl ethanethioate 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以86%的产率得到S-[2-(3,4-dihydroxyphenyl)ethyl] thioacetate
  参考文献：
  名称：

  Enhanced chemopreventive activity of hydroxytyrosol on HL60 and HL60R cells by chemical conversion into thio derivatives

  摘要：

  Thio derivatives of hydroxytyrosol containing thiol, thioacetate and disulfide functionalities were synthesized from natural hydroxytyrosol (3,4-DHPEA) via 3,4-dihydroxyphenethyl halides. These compounds, containing the combination of catechol moiety and divalent sulfur functions, were tested for the proapoptotic and anti-proliferative activities on both parental HL60 and multi-drug resistant HL60R cells. It was found that all synthesized compounds were more effective than 3,4-DHPEA in inducing apoptosis on HL60R cells, and that the hydroxytyrosol disulfide was the most active pro-apoptotic and anti-proliferative compound on both HL60 and HL60R cells. Different from 3,4-DHPEA, all thio derivatives of hydroxytyrosol induced apoptosis by a mechanism not involving the release of H2O2 in the culture medium. The data on HL60R cells suggest that these compounds could be able to reverse the resistance toward the most common drugs in cancer therapy. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2012.12.028
• 作为产物：
  描述：

  1-氯-2-(3,4-二羟基苯基)乙烷 在 吡啶 作用下， 以 丁酮 为溶剂， 反应 30.0h， 生成 S-2-(3,4-diacetoxyphenyl)ethyl ethanethioate
  参考文献：
  名称：

  Enhanced chemopreventive activity of hydroxytyrosol on HL60 and HL60R cells by chemical conversion into thio derivatives

  摘要：

  Thio derivatives of hydroxytyrosol containing thiol, thioacetate and disulfide functionalities were synthesized from natural hydroxytyrosol (3,4-DHPEA) via 3,4-dihydroxyphenethyl halides. These compounds, containing the combination of catechol moiety and divalent sulfur functions, were tested for the proapoptotic and anti-proliferative activities on both parental HL60 and multi-drug resistant HL60R cells. It was found that all synthesized compounds were more effective than 3,4-DHPEA in inducing apoptosis on HL60R cells, and that the hydroxytyrosol disulfide was the most active pro-apoptotic and anti-proliferative compound on both HL60 and HL60R cells. Different from 3,4-DHPEA, all thio derivatives of hydroxytyrosol induced apoptosis by a mechanism not involving the release of H2O2 in the culture medium. The data on HL60R cells suggest that these compounds could be able to reverse the resistance toward the most common drugs in cancer therapy. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2012.12.028