S-2-acetyl-5-methoxyphenyl N,N-dimethylcarbamothioate | 107514-49-8

• 英文名称: S-2-acetyl-5-methoxyphenyl N,N-dimethylcarbamothioate
• 英文别名: S-(2-acetyl-5-methoxyphenyl) N,N-dimethylcarbamothioate
• CAS: 107514-49-8
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: BELQPDYGHPYIKM-UHFFFAOYSA-N

物化性质

• 沸点：
  395.6±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-2-acetyl-5-methoxyphenyl N,N-dimethylcarbamothioate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以79%的产率得到2-Hydroxy-7-methoxythiochromen-4-one
  参考文献：
  名称：

  Novel cyclization of S-(o-acetylaryl) dimethylthiocarbamates. A new synthesis of 3-hydroxybenzothiophenes and 2-hydroxythiochromones

  摘要：

  DOI：

  10.1021/jo00385a005
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 、 丙酮 为溶剂， 反应 70.0h， 生成 S-2-acetyl-5-methoxyphenyl N,N-dimethylcarbamothioate
  参考文献：
  名称：

  Novel cyclization of S-(o-acetylaryl) dimethylthiocarbamates. A new synthesis of 3-hydroxybenzothiophenes and 2-hydroxythiochromones

  摘要：

  DOI：

  10.1021/jo00385a005

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.
• LAU C. K.; BELANGER P. C.; DUFRESNE C.; SCHEIGETZ J., J. ORG. CHEM., 52,(1987) N 9, 1670-1673
  作者：LAU C. K.、 BELANGER P. C.、 DUFRESNE C.、 SCHEIGETZ J.

  DOI：——

  日期：——