(5Z)-2-amino-5-benzylidene-5,6-dihydro-1,3-thiazin-4-one | 1010833-14-3

• 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)-2-amino-5-benzylidene-5,6-dihydro-1,3-thiazin-4-one
• 英文别名: (5Z)-2-amino-5-benzylidene-1,3-thiazin-4-one
• CAS: 1010833-14-3
• 化学式: C₁₁H₁₀N₂OS
• 分子量: 218.279
• InChiKey: YPYRMIWKIVIMHB-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  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-benzylidene-5,6-dihydro-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82%的产率得到(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
• 作为产物：
  描述：

  (Z)-methyl 2-(bromomethyl)-3-phenylacrylate 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 生成 (5Z)-2-amino-5-benzylidene-5,6-dihydro-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

• Exploring the reaction of multifunctional allylic bromides with N,S-dinucleophiles: isothiouronium salts and analogs as useful motifs to assemble the 1,3-thiazine core
  作者：Marcus Mandolesi Sá、Misael Ferreira、Adailton J. Bortoluzzi、Luciano Fernandes、Silvio Cunha

  DOI：10.3998/ark.5550190.0011.b24

  日期：——

  The reactivity profile of allylic bromides (derived from the Morita-Baylis-Hillman reaction) towards thiourea derivatives and further transformations of the resulting isothiuronium bromides are described. Isothiuronium salts, prepared in near quantitative yields, undergo a selective acetylation or a base-promoted intramolecular cyclization to give 2-amino-1,3-thiazin-4-ones in good overall yields.

  描述了烯丙基溴化物（源自 Morita-Baylis-Hillman 反应）对硫脲衍生物的反应性以及所得异硫脲溴化物的进一步转化。异硫脲盐以接近定量的产率制备，经过选择性乙酰化或碱促进的分子内环化，以良好的总产率得到 2-amino-1,3-thiazin-4-ones。除了反应、条件和纯化步骤的简单性之外，这里介绍的方法还提供了高纯度的产品。X 射线衍射分析明确证实了代表性化合物的结构特征。
• 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。