8-chloronaphtho[2,3-b]thiophene-4,9-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-chloronaphtho[2,3-b]thiophene-4,9-dione
• 英文别名: 8-chloro-naphtho[2,3-b]thiophene-4,9-quinone；8-Chlor-naphtho[2,3-b]thiophen-4,9-chinon；8-Chlorobenzo[f][1]benzothiole-4,9-dione；8-chlorobenzo[f][1]benzothiole-4,9-dione
• 化学式: C₁₂H₅ClO₂S
• 分子量: 248.69
• InChiKey: QQLNKRKVCSZRIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-chloronaphtho[2,3-b]thiophene-4,9-dione 在 硫酸 、 sodium carbonate 、 硝基苯 、 copper dichloride 作用下， 生成 aminonaphtho[2,3-b]-thiophene-4,9-dione
  参考文献：
  名称：

  The Synthesis of Thiophanthraquinones from Thenoyl and Thenylbenzoic Acids

  摘要：

  DOI：

  10.1021/ja01137a032
• 作为产物：
  描述：

  3-chloro-2-[2]thienylmethyl-benzoic acid 在 chromium(VI) oxide 、 溶剂黄146 、 zinc(II) chloride 作用下， 生成 8-chloronaphtho[2,3-b]thiophene-4,9-dione
  参考文献：
  名称：

  The Synthesis of Thiophanthraquinones from Thenoyl and Thenylbenzoic Acids

  摘要：

  DOI：

  10.1021/ja01137a032

文献信息

• Synthesis and Structure–Activity Relationships of Lapacho Analogues. 2. Modification of the Basic Naphtho[2,3-<i>b</i>]furan-4,9-dione, Redox Activation, and Suppression of Human Keratinocyte Hyperproliferation by 8-Hydroxynaphtho[2,3-<i>b</i>]thiophene-4,9-diones
  作者：Sven Bannwitz、Dirk Krane、Silke Vortherms、Tobias Kalin、Cathrin Lindenschmidt、Nader Zahedi Golpayegani、Jan Tentrop、Helge Prinz、Klaus Müller

  DOI：10.1021/jm500754d

  日期：2014.7.24

  of linearly anellated lapacho quinones, naphtho[2,3-b]furan-4,9-dione (7), was modified in the search for novel agents against keratinocyte hyperproliferation. The synthesis and structure–activity relationships of several heterocycle-fused naphthoquinones as well as a full range of 2- and 7-substituted derivatives of one of these, 8-hydroxynaphtho[2,3-b]thiophene-4,9-dione (8a), are described. Out of

  在寻找抗角质形成细胞过度增生的新型药物时，对线性带电lapacho醌naphtho [2,3 - b ] furan-4,9-dione（7）的基本结构进行了修改。几种杂环稠合萘醌的合成及其与结构和活性的关系，以及这些8-羟基萘[2,3 - b ]噻吩-4,9-二酮之一的全范围2和7取代衍生物（描述图8a）。总共71种类似物中，特别是2-thenoyl取代的26l，2-nicotinoyl取代的26m和2-oxadiazole取代的35a与抗银屑病药anthralin相比具有优势。使用HaCaT细胞作为模型评估了它们抑制角质形成细胞过度增殖的潜能，并与相对较低的对角质形成细胞的膜破坏作用相结合，这是通过从细胞质中释放出乳酸脱氢酶活性来确定的。关于作用机理，研究了在分离的酶法测定中通过一电子还原和二电子还原来还原lapacho醌的氧化还原，并在基于角质形成细胞的过度增殖测定中证实了它们产生超氧化物的潜力。
• 8-Halo-substituted naphtho[2,3-b]thiophene-4,9-diones as redox-active inhibitors of keratinocyte hyperproliferation with reduced membrane-damaging properties
  作者：Cathrin Lindenschmidt、Dirk Krane、Silke Vortherms、Lars Hilbig、Helge Prinz、Klaus Müller

  DOI：10.1016/j.ejmech.2016.01.040

  日期：2016.3

  A series of 8-chloronaphtho[2,3-b]thiophene-4,9-diones and also some 8-bromo analogues were prepared. The compounds were evaluated for their potencies to suppress keratinocyte hyperproliferation using the human keratinocyte line HaCaT as the primary test system. Structure activity relationship studies revealed that replacement of the phenolic group of an earlier series with an 8-halogen atom retained the inhibitory potency against keratinocyte hyperproliferation with IC50 values in the submicromolar range. 8-Chloro-substitution led to inhibitors that were more potent than their bromo analogues. Concomitantly, halo-substitution eliminated membrane-damaging properties as assessed by LDH release from the cytoplasm of the keratinocytes which, in contrast, were induced by the corresponding phenolic analogues. Finally, selective compounds were characterized for their ability to participate in redox cycling to generate superoxide in enzymatic and keratinocyte-based studies. (C) 2016 Elsevier Masson SAS. All rights reserved.
• The Synthesis of Thiophanthraquinones from Thenoyl and Thenylbenzoic Acids
  作者：H. E. Schroeder、V. Weinmayr

  DOI：10.1021/ja01137a032

  日期：1952.9