1,2-dihydroxy-4-(2-mercaptoethyl)benzene | 267219-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,2-dihydroxy-4-(2-mercaptoethyl)benzene
• 英文别名: 4-(2-sulfanylethyl)benzene-1,2-diol；4-(2-Mercaptoethyl)benzene-1,2-diol
• CAS: 267219-51-2
• 化学式: C₈H₁₀O₂S
• 分子量: 170.232
• InChiKey: YBSGFJJODBOFAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-dihydroxy-4-(2-mercaptoethyl)benzene 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 5-[2-(allyldithio)ethyl]-2-(phenyl)benzo[1,3,2]dioxaborole
  参考文献：
  名称：

  Dopamine selective molecularly imprinted polymers via post-imprinting modification

  摘要：

  一种新型合成的多巴胺受体，通过共价印迹技术制备，具有双齿结合位点，采用二硫键连接，这一连接在被切断后会氧化为非共价的亚硫酰基识别组。所使用的模板具有类似多巴胺的结构，通过二硫键与烯丙基基团相连，并通过环状硼酸二酯与4-乙烯基苯基团相连。聚合后，酯键被水解，二硫键被还原以去除聚合物基质中的模板部分，随后通过氧化将巯基残基转化为磺酸（后印迹过程）。该印迹聚合物在水相中选择性地吸附多巴胺，形成两点相互作用，即环状硼酸二酯的形成和与磺酸残基的静电相互作用。

  DOI：

  10.1039/b514432a
• 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 、 甲醇 、 水 、 丁酮 为溶剂， 反应 67.0h， 生成 1,2-dihydroxy-4-(2-mercaptoethyl)benzene
  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

• Organic precursors for tailored synthesis of sulfur- and nitrogen-doped mesoporous carbons: a molecular design approach
  作者：Takashi Hamada、Hiroki Nara、Minjun Kim、Hirokatsu Miyata、Yusuke Yamauchi

  DOI：10.1039/d4cc00101j

  日期：——

  Insights into tailoring heteroatom-doped mesoporous carbon are provided for enhanced electrocatalytic properties. This study focuses on the design and synthesis of sulfur-doped mesoporous carbon using a sulfur-containing monomer with a chemical structure similar to dopamine. The resulting material achieves remarkable catalytic activity for the oxygen reduction reaction.

  提供了定制杂原子掺杂介孔碳以增强电催化性能的见解。本研究重点是使用化学结构类似于多巴胺的含硫单体设计和合成硫掺杂介孔碳。所得材料对氧还原反应具有显着的催化活性。
• US4180672A
  申请人：——

  公开号：US4180672A

  公开（公告）日：1979-12-25
• [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.
• Dopamine selective molecularly imprinted polymers via post-imprinting modification
  作者：Toshifumi Takeuchi、Nobuo Murase、Hideshi Maki、Takashi Mukawa、Hideyuki Shinmori

  DOI：10.1039/b514432a

  日期：——

  A novel synthetic dopamine receptor bearing bidentate binding sites were prepared by covalent imprinting using a disulfide linkage which is cleaved and oxidized to a non-covalent sulfoxide recognition group. The used templates have dopamine-like structures connected to an allyl moiety via a disulfide and to a 4-vinylphenyl group via a cyclic boronic diester. After the polymerization, the ester bonds were hydrolyzed and the disulfide bond was reduced to remove the template moiety from the polymer matrix, followed by the oxidation to transform the thiol residues into sulfonic acid (post imprinted process). The imprinted polymer adsorbed dopamine selectively in aqueous solution with the two-point interaction, i.e. the formation of cyclic boronic diester and electrostatic interaction with the sulfonic acid residue.

  一种新型合成的多巴胺受体，通过共价印迹技术制备，具有双齿结合位点，采用二硫键连接，这一连接在被切断后会氧化为非共价的亚硫酰基识别组。所使用的模板具有类似多巴胺的结构，通过二硫键与烯丙基基团相连，并通过环状硼酸二酯与4-乙烯基苯基团相连。聚合后，酯键被水解，二硫键被还原以去除聚合物基质中的模板部分，随后通过氧化将巯基残基转化为磺酸（后印迹过程）。该印迹聚合物在水相中选择性地吸附多巴胺，形成两点相互作用，即环状硼酸二酯的形成和与磺酸残基的静电相互作用。
• 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.