(5Z)-5-benzylidene-5,6-dihydro-1,3-thiazine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: (5Z)-5-benzylidene-5,6-dihydro-1,3-thiazine-2,4-dione
• 英文别名: (5Z)-5-benzylidene-1,3-thiazinane-2,4-dione
• 化学式: C₁₁H₉NO₂S
• 分子量: 219.264
• InChiKey: UMMAVWCAWOSADO-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-methyl 2-(bromomethyl)-3-phenylacrylate 在 乙酸酐 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 (5Z)-5-benzylidene-5,6-dihydro-1,3-thiazine-2,4-dione
  参考文献：
  名称：

  Synthesis of 1,3-thiazine-2,4-diones with potential anticancer activity

  摘要：

  2-Amino-1,3-thiazin-4-ones were subjected to acetylation followed by mild acid hydrolysis to give compounds containing the 1,3-thiazine-2,4-dione core. The potential of these S,N-containing heterocycles as antitumor agents against human cancer cell lines, among other types, was evaluated. The results show that phenyl- and naphthyl-substituted thiazinediones presented selective antitumoral activity against leukemia cells. These compounds caused cell death with DNA fragmentation and the mechanism of action seems to involve caspase cascade activation, imbalance in intracellular Ca2+ and mitochondrial metabolism, and/or endoplasmic reticulum stress. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.017

文献信息

• Synthesis of 1,3-thiazine-2,4-diones with potential anticancer activity
  作者：Misael Ferreira、Laura Sartori Assunção、Fabíola Branco Filippin-Monteiro、Tânia Beatriz Creczynski-Pasa、Marcus Mandolesi Sá

  DOI：10.1016/j.ejmech.2013.10.017

  日期：2013.12

  2-Amino-1,3-thiazin-4-ones were subjected to acetylation followed by mild acid hydrolysis to give compounds containing the 1,3-thiazine-2,4-dione core. The potential of these S,N-containing heterocycles as antitumor agents against human cancer cell lines, among other types, was evaluated. The results show that phenyl- and naphthyl-substituted thiazinediones presented selective antitumoral activity against leukemia cells. These compounds caused cell death with DNA fragmentation and the mechanism of action seems to involve caspase cascade activation, imbalance in intracellular Ca2+ and mitochondrial metabolism, and/or endoplasmic reticulum stress. (C) 2013 Elsevier Masson SAS. All rights reserved.