(5,6-dimethoxybenzo[b]thiophen-2-yl)(3,4,5-trimethoxyphenyl)methanone | 1239890-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5,6-dimethoxybenzo[b]thiophen-2-yl)(3,4,5-trimethoxyphenyl)methanone
• 英文别名: (5,6-dimethoxy-1-benzothiophen-2-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1239890-26-6
• 化学式: C₂₀H₂₀O₆S
• 分子量: 388.441
• InChiKey: BGGKLYOCGRQGBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-溴-1-(3,4,5-三甲氧基苯基)乙酮 、 4,5-Dimethoxy-2-sulfanylbenzaldehyde 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以62%的产率得到(5,6-dimethoxybenzo[b]thiophen-2-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Substituted 2-(3′,4′,5′-trimethoxybenzoyl)-benzo[b]thiophene derivatives as potent tubulin polymerization inhibitors

  摘要：

  The central role of microtubules in cell division and mitosis makes them a particularly important target for anticancer agents. On our early publication, we found that a series of 2-(3',4',5'-trimethoxybenzoyl)-3-aminobenzo[b]thiophenes exhibited strong antiproliferative activity in the submicromolar range and significantly arrested cells in the G2-M phase of the cell cycle and induced apoptosis. In order to investigate the importance of the amino group at the 3-position of the benzo[b] thiophene skeleton, the corresponding 3-unsubstituted and methyl derivatives were prepared. A novel series of inhibitors of tubulin polymerization, based on the 2-(3,4,5-trimethoxybenzoyl)-benzo[b] thiophene molecular skeleton with a methoxy substituent at the C-4, C-5, C-6 or C-7 position on the benzene ring, was evaluated for antiproliferative activity against a panel of five cancer cell lines, for inhibition of tubulin polymerization and for cell cycle effects. Replacing the methyl group at the C-3 position resulted in increased activity compared with the corresponding 3-unsubstituted counterpart. The structure-activity relationship established that the best activities were obtained with the methoxy group placed at the C-4, C-6 or C-7 position. Most of these compounds exhibited good growth inhibition activity and arrest K562 cells in the G2-M phase via microtubule depolymerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.068