2,3-ethylenedioxy-1,4-benzoquinone | 42965-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶英
• 英文名称: 2,3-ethylenedioxy-1,4-benzoquinone
• 英文别名: 2,3-Dihydro-1,4-benzodioxin-5,8-dione；2,3-dihydro-1,4-benzodioxine-5,8-dione
• CAS: 42965-39-9
• 化学式: C₈H₆O₄
• mdl: MFCD18451456
• 分子量: 166.133
• InChiKey: GZHGBCNREDASAP-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159.5 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  262.1±40.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-ethylenedioxy-1,4-benzoquinone 在 三氟化硼乙醚 、 silica gel 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 0.92h， 生成 2,3-dihydronaphtho<2,3-b>-p-dioxine-5,10-quinone
  参考文献：
  名称：

  Hayakawa, Kenji; Kido, Keiko; Kanematsu, Ken, Journal of the Chemical Society. Perkin transactions I, 1988, p. 511 - 520

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-乙二氧基酚 在 盐酸 、 sodium nitrite 、 对氨基苯磺酸 作用下， 以 水 为溶剂， 反应 1.0h， 以36%的产率得到2,3-ethylenedioxy-1,4-benzoquinone
  参考文献：
  名称：

  Hayakawa, Kenji; Kido, Keiko; Kanematsu, Ken, Journal of the Chemical Society. Perkin transactions I, 1988, p. 511 - 520

  摘要：

  DOI：

文献信息

• Naphthalene anti-psoriatic agents
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04840965A1

  公开（公告）日：1989-06-20

  Naphthalenes of the formula: ##STR1## wherein: m is 1 or 2; n is 1, 2, or 3; R.sup.1 is alkyl of one to seven carbon atoms or an optionally substituted phenyl; R.sup.2 is hydrogen, lower alkyl, lower alkoxy, optionally substituted phenyl, optionally substituted phenyl-lower-alkyl, optionally substituted phenyl-lower-alkoxy, amino, lower alkylamino, lower dialkylamino, halo, cyano, hydroxy, or lower alkylthio are useful in relieving psoriasis.

  萘的化学式如下：##STR1## 其中：m为1或2；n为1、2或3；R.sup.1为含有一至七个碳原子的烷基或可选择取代的苯基；R.sup.2为氢、低烷基、低烷氧基、可选择取代的苯基、可选择取代的苯基-低烷基、可选择取代的苯基-低烷氧基、氨基、低烷基氨基、低二烷基氨基、卤素、氰基、羟基或低烷硫基，在缓解银屑病方面具有用处。
• Inhibition of mitochondrial respiratory chain by arylthiolated 2,3-ethylenedioxy-1,4-benzoquinones.
  作者：Koichi MORI、Shihoko HAMA、Fumino KATO、Tadashi OKAMOTO、Takeo KISHI、Hiroteru SAYO

  DOI：10.1248/cpb.38.1100

  日期：——

  A series of arylthiolated 2, 3-ethylenedioxy-1, 4-benzoquinones as a coenzyme Q (CoQ) antagonist was tested for inhibition of succinate oxidase and reduced nicotinamide adenine dinucleotide (NADH) oxidase systems in the mitochondrial respiratory chain. The following characteristics were revealed : (1) 2, 3-ethylenedioxy, 5-arylthio and 5, 6-diarylthio groups were confirmed to be favorable for inhibition of both systems; (2) these analogs were more effective in the succinate oxidase system than in the NADH oxidase system; (3) 4' substituents on the benzene side ring had little effect on inhibitory activity; (4) the acting sites of these analogs had no strict stereospecificity. The reduced minus oxidized difference spectra revealed that these analogs inhibited the succinate oxidase system at the site between succinate and CoQ, and the NADH oxidase system at the site after cytochrome a+a3, suggesting these analogs might act as antagonists of CoQ in the succinate oxidase system. However, 5-(4'-nitrophenylthio)-2, 3-ethylenedioxyl-1, 4-benzoquinone (If) strongly inhibited only the succinate oxidase system at the site after cytochrome a+a3.

  研究人员测试了一系列芳硫基 2，3-乙烯二氧基-1，4-苯醌类化合物作为辅酶 Q（CoQ）拮抗剂对线粒体呼吸链中琥珀酸氧化酶和还原型烟酰胺腺嘌呤二核苷酸（NADH）氧化酶系统的抑制作用。结果表明：(1) 2, 3-乙烯二氧基、5-芳硫基和 5, 6-二芳硫基被证实对这两个系统都有抑制作用；(2) 这些类似物对琥珀酸氧化酶系统的抑制作用大于对 NADH 氧化酶系统的抑制作用；(3) 苯侧环上的 4' 取代基对抑制活性的影响很小；(4) 这些类似物的作用位点没有严格的立体特异性。还原减氧化差谱显示，这些类似物在琥珀酸与 CoQ 之间的部位抑制琥珀酸氧化酶系统，在细胞色素 a+a3 之后的部位抑制 NADH 氧化酶系统，表明这些类似物可能在琥珀酸氧化酶系统中作为 CoQ 的拮抗剂。然而，5-（4'-硝基苯硫基）-2，3-亚乙二氧基-1，4-苯醌（If）仅能强烈抑制细胞色素 a+a3 后部位的琥珀酸氧化酶系统。
• 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。
• Topical nonsteroidal antipsoriatic agents. 2. 2,3-(Alkylidenedioxy)naphthalene analogs of lonapalene
  作者：Michael C. Venuti、Brad E. Loe、Gordon H. Jones、John M. Young

  DOI：10.1021/jm00119a013

  日期：1988.11

  A series of 2,3-(alkylidenedioxy)naphthalene (5a-p) analogues of lonapalene (RS-43179, 1), a 5-lipoxygenase inhibitor currently under clinical investigation for the treatment of psoriasis, has been prepared and evaluated for topical inhibitory activity against arachidonic acid induced mouse ear edema. The results of these studies demonstrate that introduction of the fused 2,3-alkylidenedioxy ring, in place of the acyclic 2,3-dialkoxy substituent pattern characteristic of the previous series, caused a modest dimunition in overall potency within the series. These results suggest a potential steric intolerance for these extended planar analogues, in comparison with their 2,3-dialkoxy predecessors.
• JONES, GORDON H.;VENUTI, MICHAEL C.;YOUNG, JOHN M.
  作者：JONES, GORDON H.、VENUTI, MICHAEL C.、YOUNG, JOHN M.

  DOI：——

  日期：——