2-Acetyl-naphtho[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: 2-Acetyl-naphtho[2,3-b]thiophene-4,9-dione
• 英文别名: 2-aetylnaphtho[2,3-b]thiophene-4,9-dione；2-acetylnaphto[2,3-b]thiophene-4,8-dione；2-Acetyl naphtho[2,3-b]thiophene-4,9-dione；2-acetylbenzo[f][1]benzothiole-4,9-dione
• 化学式: C₁₄H₈O₃S
• 分子量: 256.282
• InChiKey: AZJPKGXMDKTLMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯并[f][1]苯并二硫杂环戊烷 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 2-Acetyl-naphtho[2,3-b]thiophene-4,9-dione
  参考文献：
  名称：

  Lapacho类似物的合成及其构效关系。2.碱性萘并[2,3 - b ]呋喃-4,9-二酮的修饰，氧化还原活化和8-羟基萘并[2,3 - b ]噻吩-4,9-二酮对人角质形成细胞过度增殖的抑制作用

  摘要：

  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。

  DOI：

  10.1021/jm500754d

文献信息

• Naphtho- and dihydrobenzo-thiophene derivatives as cytotoxic antitumor agents
  申请人：University of North Carolina at Chapel Hill

  公开号：US06337346B1

  公开（公告）日：2002-01-08

  Compounds useful as cytotoxic agents are selected from the group consisting of compounds of Formula I and compounds of Formula II: wherein: R1, R2, R3 and R4 are each independently selected from the group consisting of: hydrogen, alkyl, carboxy, alkoxy, hydroxyalkyl, alkylcarbonyl; alkylcarbonyloxy; alkyl substituted with alkylcarbonyloxy, thiophenylcarbonyl; nitro and cyano; thiophenyl and thiophenylthiophenyl, each of which may be unsubstituted or substituted with alkyl, carboxy, alkoxy, hydroxyalkyl, alkylcarbonyl; alkylcarbonyloxy; alkyl substituted with alkylcarbonyloxy, nitro or cyano; subject to the proviso that at least one of R1, R2, R3 and R4 is not hydrogen; A1 and A2 are each selected from the group consisting of: ═O, alkyl, alkoxy, and alkylcarbonyloxy; and the pharmaceutically acceptable salts thereof. When A1 and A2 are ═O, the center ring has only two, and not three, double bonds.

  作为细胞毒性剂有用的化合物是从以下化合物组中选择的：公式I的化合物和公式II的化合物： 其中：R1、R2、R3和R4分别独立地选择自以下组合物：氢、烷基、羧基、烷氧基、羟基烷基、烷基羰基、烷基羰氧基、烷基取代的烷基羰氧基、硫代苯基羰基、硝基和氰基；硫代苯基和硫代苯基硫代苯基，每种可能未取代或取代为烷基、羧基、烷氧基、羟基烷基、烷基羰基、烷基羰氧基、烷基取代的烷基羰氧基、硝基或氰基；但至少其中一个R1、R2、R3和R4不是氢；A1和A2分别选择自以下组合物：═O、烷基、烷氧基和烷基羰氧基；及其药用盐。当A1和A2为═O时，中心环只有两个双键，而不是三个。
• Novel lapacho compounds and methods of use thereof
  申请人：Muller Klaus

  公开号：US20060142271A1

  公开（公告）日：2006-06-29

  The invention provides new synthetic lapacho derivatives as well as methods of use thereof. These compounds can be used in pharmaceutical compositions for the treatment or prevention of cell proliferation disorders. These compounds can also be used in the treatment or prevention of psoriasis or cancer or precancerous conditions.

  本发明提供了新的合成拉帕昔衍生物及其使用方法。这些化合物可以用于制备药物组合物，用于治疗或预防细胞增殖障碍。这些化合物还可以用于治疗或预防牛皮癣、癌症或癌前病变。
• NOVEL STAT3 PATHWAY INHIBITORS AND CANCER STEM CELL INHIBITORS
  申请人：Jiang Zhiwei

  公开号：US20110112180A1

  公开（公告）日：2011-05-12

  The present invention relates to a novel naphtho class of compounds as Stat3 pathway inhibitors and as cancer stem cell inhibitors; to methods of using such compounds to treat cancer; to methods of using such compounds to treat disorders in a mammal related to aberrent Stat3 pathway activity; to pharmaceutical compositions containing such compounds.

  本发明涉及一种新型的萘类化合物，作为Stat3通路抑制剂和癌症干细胞抑制剂；以及使用这些化合物治疗癌症的方法；以及使用这些化合物治疗与哺乳动物中异常Stat3通路活性相关的疾病的方法；以及含有这些化合物的药物组合物。
• Stat3 pathway inhibitors and cancer stem cell inhibitors
  申请人：Sumitomo Dainippon Pharma Oncology, Inc.

  公开号：US10851075B2

  公开（公告）日：2020-12-01

  The present invention relates to a novel naphtho class of compounds as Stat3 pathway inhibitors and as cancer stem cell inhibitors; to methods of using such compounds to treat cancer; to methods of using such compounds to treat disorders in a mammal related to aberrent Stat3 pathway activity; to pharmaceutical compositions containing such compounds.

  本发明涉及作为Stat3通路抑制剂和癌症干细胞抑制剂的一类新型萘化合物；涉及使用此类化合物治疗癌症的方法；涉及使用此类化合物治疗哺乳动物体内与Stat3通路活性异常有关的疾病的方法；涉及含有此类化合物的药物组合物。
• Synthesis and cytotoxicity of acetyl-4H, 9H-naphtho[2,3-b]thiophene-4,9-diones
  作者：Li-Jiau Huang、Sheng-Chu Kuo、Cherng-Yih Perng、Yu-Hua Chao、Tian-Shung Wu、Andrew T. McPhail、Anthony Mauger、Huey-Hwa Cheng、Kuo-Hsiung Lee

  DOI：10.1016/s0960-894x(98)00496-x

  日期：1998.10

  Several new acetyl-4H,9H-naphtho[2,3-b]thiophene-4,9-diones were synthesized and evaluated for in vitro cytotoxicity by NCI against seven cancer cell types. 2,7-Diacetyl naphtho[2,3-b]thiophene-4,9-dione (9) showed significant cytotoxicity against leukemia cells with log GI50 values of -7.61 against SR cells and -7.18 against MOLT-4 cells. 3-Acetyl-naphtho[2,3-b]thiophene-4,9-dione (6) also demonstrated potent cytotoxicity in the latter cell line with log GI50 < -8.