1-(3-甲氧基-2-硫烷基苯基)乙酮 | 846577-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-甲氧基-2-硫烷基苯基)乙酮
• 英文名称: 2-acetyl-6-methoxythiophenol
• 英文别名: 1-(3-Methoxy-2-sulfanylphenyl)ethan-1-one；1-(3-methoxy-2-sulfanylphenyl)ethanone
• CAS: 846577-58-0
• 化学式: C₉H₁₀O₂S
• 分子量: 182.243
• InChiKey: UYJHKWZHVXLNOD-UHFFFAOYSA-N

物化性质

• 沸点：
  290.7±30.0 °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：

  1-(3-甲氧基-2-硫烷基苯基)乙酮 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 17.0h， 生成 (8-Methoxy-4-methyl-2-oxo-2H-thiochromen-3-ylamino)-acetic acid methyl ester
  参考文献：
  名称：

  新型 8-METHOXY-4-METHYL-3-(N-[2'-AMINO-(1',3',4')THIA/OXA-DIAZOL-5'-YL]-取代甲基)-氨基硫香豆素的合成

  摘要：

  8-Methoxy-4-methyl-3-(N-[2'-amino-(1', 3',4')thia/oxa-diazol-5'-yl] 取代的甲基)-氨基硫香豆素 6(a– f) 和 7(a-f)，是通过使用未报道的 8-甲氧基-4-甲基-3-[N-(2'-氧代-2'-甲氧基-1'-取代的乙烷-1'-基) 氨基硫香豆素作为关键中间体。

  DOI：

  10.1080/10426500490474914
• 作为产物：
  描述：

  S-2-acetyl-6-methoxyphenyl N,N-dimethylcarbamothioate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 为溶剂， 生成 1-(3-甲氧基-2-硫烷基苯基)乙酮
  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

• Substituted 2-(3′,4′,5′-trimethoxybenzoyl)-benzo[b]thiophene derivatives as potent tubulin polymerization inhibitors
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Olga Cruz-Lopez、Manlio Tolomeo、Stefania Grimaudo、Antonietta Di Cristina、Maria Rosaria Pipitone、Jan Balzarini、Andrea Brancale、Ernest Hamel

  DOI：10.1016/j.bmc.2010.05.068

  日期：2010.7

  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.
• SYNTHESIS OF NEW 8-METHOXY-4-METHYL-3-(N-[2^′-AMINO-(1′,3′,4′)THIA/OXA-DIAZOL-5′-YL]-SUBSTITUTED METHYL)-AMINO THIOCOUMARINS
  作者：B. Prasanna、G. V. P. Chandramouli

  DOI：10.1080/10426500490474914

  日期：2004.10.1

  8-Methoxy-4-methyl-3-(N-[2′-amino-(1′, 3′,4′)thia/oxa-diazol-5′-yl] substituted methyl)-amino thiocoumarins 6(a–f) and 7(a–f), were synthesized by using the unreported 8-methoxy-4-methyl-3-[N-(2′-oxo-2′-methoxy-1′-substituted ethan-1′-yl) amino thiocoumarins as key intermediates.

  8-Methoxy-4-methyl-3-(N-[2'-amino-(1', 3',4')thia/oxa-diazol-5'-yl] 取代的甲基)-氨基硫香豆素 6(a– f) 和 7(a-f)，是通过使用未报道的 8-甲氧基-4-甲基-3-[N-(2'-氧代-2'-甲氧基-1'-取代的乙烷-1'-基) 氨基硫香豆素作为关键中间体。