2'-Mercapto-6'-methoxyacetophenon | 83080-84-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-Mercapto-6'-methoxyacetophenon
• 英文别名: 1-(2-methoxy-6-sulfanylphenyl)ethanone
• CAS: 83080-84-6
• 化学式: C₉H₁₀O₂S
• 分子量: 182.243
• InChiKey: UPIFWAQTPPDHBS-UHFFFAOYSA-N

物化性质

• 沸点：
  299.1±25.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-1-(3,4,5-三甲氧基苯基)乙酮 、 2'-Mercapto-6'-methoxyacetophenon 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以60%的产率得到(4-methoxy-3-methylbenzo[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
• 作为产物：
  描述：

  S-2-acetyl-3-methoxyphenyl N,N-dimethylcarbamothioate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 为溶剂， 生成 2'-Mercapto-6'-methoxyacetophenon
  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

文献信息

• Einfache Darstellung von Aldehyden der Chromanon‐ und Thiochromanon‐Reihe, Schlüsselprodukten für die Synthese von 6‐Heterotetracyclinen
  作者：Richard Kirchlechner

  DOI：10.1002/cber.19821150708

  日期：1982.7

  Eine neue und einfache Methode zur Darstellung von Aldehyden in der Chromanon- und Thiochromanon-Reihe wurde in der Kondensation von o-Hydroxy- oder o-Mercapto-acetophenonen mit einem vinylogen Formamidiniumsalz gefunden.

  在邻羟基-或邻巯基乙酰苯与乙烯基甲酰胺盐的缩合反应中发现了一种新的简单方法，用于制备苯并二氢吡喃和苯并二氢吡喃酮。