4-acetoxy-2-acetylbenzo<1,2-b:5,4-b'>dithiophene | 251540-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 4-acetoxy-2-acetylbenzo<1,2-b:5,4-b'>dithiophene
• 英文别名: 4-acetoxy-2-acetylbenzo[1,2-b:5,4-b']dithiophene；(2-Acetylthieno[3,2-f][1]benzothiol-4-yl) acetate
• CAS: 251540-00-8
• 化学式: C₁₄H₁₀O₃S₂
• 分子量: 290.364
• InChiKey: HPIKGLDMFGUNRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetoxy-2-acetylbenzo<1,2-b:5,4-b'>dithiophene 在 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 1.0h， 生成 2-acetyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 2-Acetyl-4,8-dihydrobenzodithiophene-4,8-dione Derivatives

  摘要：

  2-Acetyl-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (9) and 2-acetyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione (19), together with 10 related mono- and disubstituted derivatives, were synthesized and evaluated in vitro by NCI against eight cancer types. All compounds showed significant activity against melanoma, HL-60 leukemia, NCI-H23 non-small-cell lung cancer, OVCAR-3 ovarian cancer, and MDA-MB-435 and MDA-N breast cancer cell lines. Compound 11, 2-(1'-acetoxyethyl)-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione, showed the highest overall potency (mean GI(50) = 40 nM).

  DOI：

  10.1021/jm980394t
• 作为产物：
  描述：

  4-acetoxybenzo<1,2-b:5,4-b'>dithiophene 、 乙酰氯 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 4-acetoxy-2-acetylbenzo<1,2-b:5,4-b'>dithiophene
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 2-Acetyl-4,8-dihydrobenzodithiophene-4,8-dione Derivatives

  摘要：

  2-Acetyl-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (9) and 2-acetyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione (19), together with 10 related mono- and disubstituted derivatives, were synthesized and evaluated in vitro by NCI against eight cancer types. All compounds showed significant activity against melanoma, HL-60 leukemia, NCI-H23 non-small-cell lung cancer, OVCAR-3 ovarian cancer, and MDA-MB-435 and MDA-N breast cancer cell lines. Compound 11, 2-(1'-acetoxyethyl)-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione, showed the highest overall potency (mean GI(50) = 40 nM).

  DOI：

  10.1021/jm980394t

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。