(5Z)-2-amino-5,6-dihydro-5-[(E)-3-phenyl-2-propenylidene]-1,3-thiazin-4-one | 1010833-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5Z)-2-amino-5,6-dihydro-5-[(E)-3-phenyl-2-propenylidene]-1,3-thiazin-4-one
• 英文别名: (5Z)-2-amino-5-[(E)-3-phenylprop-2-enylidene]-1,3-thiazin-4-one
• CAS: 1010833-19-8
• 化学式: C₁₃H₁₂N₂OS
• 分子量: 244.317
• InChiKey: FIVPMORLINYVPD-VCABWLAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5Z)-2-amino-5,6-dihydro-5-[(E)-3-phenyl-2-propenylidene]-1,3-thiazin-4-one 在 乙酸酐 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以85%的产率得到(5Z)-5,6-dihydro-5-[(E)-3-phenyl-2-propenylidene]-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
• 作为产物：
  描述：

  methyl (2Z,4E)-2-(bromomethyl)-5-phenylpenta-2,4-dienoate 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 生成 (5Z)-2-amino-5,6-dihydro-5-[(E)-3-phenyl-2-propenylidene]-1,3-thiazin-4-one
  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 allylic thiocyanates and novel 1,3-thiazin-4-ones from 2-(bromomethyl)alkenoates and S-nucleophiles in aqueous medium
  作者：Marcus M. Sá、Luciano Fernandes、Misael Ferreira、Adailton J. Bortoluzzi

  DOI：10.1016/j.tetlet.2007.12.029

  日期：2008.2

  Allylic thiocyanates and novel heterocycles containing the 1,3-thiazin-4-one core are easily obtained in high yields and mild conditions by nucleophilic displacement of 2-(bromomethyl)alkenoates (derived from Morita–Baylis–Hillman adducts) with sulphur-centred nucleophiles in aqueous acetone at 25 °C. Treatment of allylic bromides with NaSCN gave the corresponding (Z)-2-(thiocyanomethyl)alkenoates

  通过亲核取代2-（溴甲基）链烯酸酯（衍生自Morita-Baylis-Hillman加合物）并以硫为中心，可以容易地以高收率和温和条件获得烯丙基硫氰酸酯和含有1,3-噻嗪-4-one核的新型杂环丙酮水溶液中的亲核试剂，温度为25°C。用NaSCN处理烯丙基溴化物得到相应的（Z）-2-（硫氰基甲基）链烯酸酯，然后与硫脲反应，然后进行碱性后处理，选择性地制备了（5 Z）-2-氨基-5-芳基-1,3 -噻嗪-4-酮。通过X射线衍射分析确认了结构分配。