(3,4-dihydroxyphenethyl)disulfide | 1415490-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3,4-dihydroxyphenethyl)disulfide
• 英文别名: 4-[2-[2-(3,4-Dihydroxyphenyl)ethyldisulfanyl]ethyl]benzene-1,2-diol；4-[2-[2-(3,4-dihydroxyphenyl)ethyldisulfanyl]ethyl]benzene-1,2-diol
• CAS: 1415490-08-2
• 化学式: C₁₆H₁₈O₄S₂
• 分子量: 338.449
• InChiKey: UECYAYAJWBVTHO-UHFFFAOYSA-N

物化性质

• 沸点：
  610.1±55.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  羟基酪醇 在 吡啶 、 咪唑 、 盐酸 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丁酮 为溶剂， 反应 57.0h， 生成 (3,4-dihydroxyphenethyl)disulfide
  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

文献信息

• [EN] BIOACTIVE POLYPHENOLIC COMPOUNDS CONTAINING SULPHUR OR SELENIUM AND USES THEREOF<br/>[ES] COMPUESTOS BIOACTIVOS POLIFENÓLICOS CONTENIENDO AZUFRE O SELENIO Y SUS USOS<br/>[FR] COMPOSÉS BIOACTIFS POLYPHÉNOLYQUES CONTENANT DU SOUFRE OU DU SÉLÉNIUM ET UTILISATIONS DE CEUX-CI
  申请人：UNIV SEVILLA

  公开号：WO2012164118A1

  公开（公告）日：2012-12-06

  La invención se refiere a compuestos que contienen al menos un grupo polifenol y azufre o selenio y sus usos como antioxidantes y captadores de radicales libres. Además, se refiere a las composiciones farmacéuticas, nutracéuticas y cosméticas que los incluyen.
• Enhanced chemopreventive activity of hydroxytyrosol on HL60 and HL60R cells by chemical conversion into thio derivatives
  作者：Maria Vittoria Sepporta、M. Ángeles López-García、Roberto Fabiani、Inés Maya、José G. Fernández-Bolaños

  DOI：10.1016/j.ejps.2012.12.028

  日期：2013.3

  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.