8-trifluoromethylnaphtho[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-trifluoromethylnaphtho[2,3-b]thiophene-4,9-dione
• 英文别名: 8-(Trifluoromethyl)benzo[f][1]benzothiole-4,9-dione；8-(trifluoromethyl)benzo[f][1]benzothiole-4,9-dione
• 化学式: C₁₃H₅F₃O₂S
• 分子量: 282.243
• InChiKey: CTDZBBULESCICV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  aminonaphtho[2,3-b]-thiophene-4,9-dione 在 copper(l) iodide 、 溶剂黄146 、 sodium nitrite 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 6.0h， 生成 8-trifluoromethylnaphtho[2,3-b]thiophene-4,9-dione
  参考文献：
  名称：

  8-Halo-substituted naphtho[2,3-b]thiophene-4,9-diones as redox-active inhibitors of keratinocyte hyperproliferation with reduced membrane-damaging properties

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2016.01.040

文献信息

• 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.