5-phenylthio-2,3-ethylenedioxy-1,4-benzoquinone | 120082-91-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-phenylthio-2,3-ethylenedioxy-1,4-benzoquinone
• 英文别名: 6-Phenylsulfanyl-2,3-dihydro-1,4-benzodioxine-5,8-dione
• CAS: 120082-91-9
• 化学式: C₁₄H₁₀O₄S
• 分子量: 274.297
• InChiKey: UGHAOICZTFKJBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-ethylenedioxy-1,4-benzoquinone 、 苯硫酚 在 potassium nitrososulfonate 、 sodium acetate 作用下， 生成 5-phenylthio-2,3-ethylenedioxy-1,4-benzoquinone 、 5,6-diphenylthio-2,3-ethylenedioxy-1,4-benzoquinone 、 二苯二硫醚
  参考文献：
  名称：

  Inhibition of succinoxidase and reduced nicotinamide adenine dinucleotide (NADH) oxidase by 2,3-ethlenedioxy-1,4-benzoquinones having alkylthio and arythio side chains.

  摘要：

  -a+a3。

  DOI：

  10.1248/cpb.37.221

文献信息

• Inhibition of succinoxidase and reduced nicotinamide adenine dinucleotide (NADH) oxidase by 2,3-ethlenedioxy-1,4-benzoquinones having alkylthio and arythio side chains.
  作者：Koichi MORI、Chieko TERASHITA、Yuko FUKUNAGA、Tadashi OKAMOTO、Taeko KISHI、Hiroteru SAYO

  DOI：10.1248/cpb.37.221

  日期：——

  A series of 2, 3-ethylenedioxy-1, 4-benzoquinones having an alkylthio or arylthio side chain at the 5-position or two alkylthio or arylthio side chains at the 5, 6-positions was synthesized. These compounds were tested for inhibition of the succinoxidase and reduced nicotinamide adenine dinucleotide (NADH) oxidase systems in the mitochondrial respiratory chain. 5-Arylthio- and 5, 6-diarylthio-2, 3-ethylenedioxy-1, 4-benzoquinones were found to show potent inhibitory activities toward both enzyme systems. However, 5-alkylthio- and 5, 6-dialkylthio-2, 3-ethylenedioxy-1, 4-benzoquinones showed weak inhibitory activities. The substitution of a 2, 3-ethylenedioxy group in place of the 2, 3-dimethoxy group of coenzyme Q (CoQ) was found to be more favorable than the previously reported 2, 3-dimethyl compound or 1, 4-naphthoquinones for the inhibition of both enzyme systems. The effects of 2, 3-ethylenedioxy-1, 4-benzoquinones on the reduced minus oxidized difference spectra of submitochondrial particles with succinate or NADH as a substrate were investigated to identify their inhibitory sites in the respiratory chain. The spectral changes suggested that 5-arylthio- and 5, 6-diarylthio-2, 3-ethylenedioxy-1, 4-benzoquinones inhibit some sites between succinate and CoQ, as well as after cytochrome a+a3. On the other hand, 5, 6-dialkylthio-2, 3-ethylenedioxy-1, 4-benzoquinones were found to inhibit some sites between NADH and CoQ, as well as after chrochrome a+a3.

  -a+a3。