2H-3-methyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine | 78545-39-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2H-3-methyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
• 英文别名: 6-methyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine；6-methyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thidiazine
• CAS: 78545-39-8
• 化学式: C₅H₆N₄S
• 分子量: 154.195
• InChiKey: NBQHMFSAAZMTTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [RuCl4(DMSO)2]Na 、 2H-3-methyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 以 乙腈 为溶剂， 以78%的产率得到Na[trans-RuCl2(DMSO)(2H-3-methyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine)]
  参考文献：
  名称：

  Synthesis, structural characterisation and solution chemistry of ruthenium(III) triazole-thiadiazine complexes

  摘要：

  合成了两个与抗癌化合物NAMI在结构上相似的铑(III)配合物：Na[RuCl4(DMSO)(L1)] (1)和Na[RuCl4(DMSO)(L2)] (2)，其中L1和L2是不同功能化的噻二嗪-三唑配体。为了促进配合物阴离子的结晶，将Na+替换为[双(triphenylphosphoranylidene)铵]阳离子(PPN+)，从而实现对PPN[RuCl4(DMSO)(L1)]·2H2O (1a·2H2O)和PPN[RuCl4(DMSO)(L2)]·3H2O (2a·3H2O)的X射线表征。这两种化合物经历逐步的水解过程，通过紫外-可见光谱和1H核磁共振光谱进行评估。第一次水解步骤是用水分子替换一个氯离子，半衰期分别为50分钟(1)和110分钟(2)，而后续的水解步骤更复杂，因为同时生成不止一种产物。Ru(III)/Ru(II)对的氧化还原电位(1为0.31 V，2为0.28 V)表明这些配合物可以在细胞内环境中被还原，这与为NAMI和NAMI-A提出的“还原激活”机制相一致。1和2在来自纤维肉瘤(HT1080)的人癌细胞系和非癌性初级人类成纤维细胞(HF)中进行了测试，结果显示出适度的抑制效果。

  DOI：

  10.1039/b823271g
• 作为产物：
  描述：

  3-prop-2-ynylsulfanyl-1,2,4-triazol-4-amine;hydrobromide 以20%的产率得到
  参考文献：
  名称：

  RUDNICKA W.; SAWLEWICZ J., ACTA POL. PHARM., 1980, 37, NO 4, 391-396

  摘要：

  DOI：

文献信息

• Solid Acid Induced Cyclocondensation: A Facile, One-Pot Synthesis of 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines
  作者：M. M. Heravi、M. Bakherad、M. Rahimzadeh、M. Bakavoli

  DOI：10.1080/10426500214303

  日期：2002.10

  7H-[1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines are synthesized in good yields by the catalytic action of sulfuric acid adsorbed on sillica gel. Starting from 4-amino-5-substituted-1,2,4-triazole-3-thiones and employing cyclocondensation reaction with f -chloroacetonitrile and f -haloketones, the desired triazolothiadiazines have been synthesized satisfactorilly.

  7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪通过吸附在硅胶上的硫酸的催化作用以良好的产率合成。以4-氨基-5-取代-1,2,4-三唑-3-硫酮为原料，与f-氯乙腈和f-卤代酮进行环缩缩合反应，成功合成了所需的三唑噻二嗪。
• Pyrolytic desulfurization ring contraction of condensed thiadiazines as a general route towards pyrazoloazines and pyrazoloazoles with a bridgehead (ring junction) nitrogen atom
  作者：Yehia A. Ibrahim、Nouria A. Al-Awadi、Elizabeth John

  DOI：10.1016/j.tet.2008.08.067

  日期：2008.11

  Pyrolytic conversion of [1,2,4]triazino[3,4-b][1,3,4]thiadiazin-4-ones, [1,3,4]thiadiazino[2,3-b]quinazolin-10-ones and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines into their corresponding pyrazolo[5,1-c][1,2,4]triazin-4-ones, Pyrazolo[4,3-b]quinazolin-9-ones and pyrazolo[5,1-b][1,2,4]triazoles via desulfurization ring contraction is described. The starting condensed 1,3,4-thiadiazines were prepared from the corresponding readily available 4-amino-3-thioxo-1,2,4-triazin-5(4H)-ones, 3-amino-2,3-dihydro-2-thioxo-quinazolin-4(1H)-one and 4-amino-3(2H)-thioxo-1,2,4-triazoles upon reaction with the appropriate alpha-haloketones in two steps, or directly in one step in ethylpyridinium tetrafluoroborate (ionic liquid, IL). (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, structural characterisation and solution chemistry of ruthenium(III) triazole-thiadiazine complexes
  作者：Massimiliano Delferro、Luciano Marchiò、Matteo Tegoni、Saverio Tardito、Renata Franchi-Gazzola、Maurizio Lanfranchi

  DOI：10.1039/b823271g

  日期：——

  Two ruthenium(III) complexes structurally similar to the anticancer compound NAMI were prepared: Na[RuCl4(DMSO)(L1)] (1) and Na[RuCl4(DMSO)(L2)] (2), where L1 and L2 are differently functionalised triazole-thiadiazine ligands. To facilitate the crystallisation of the complex anions, Na+ was substituted with the [bis(triphenylphosphoranylidene)ammonium] cation (PPN+), allowing the X-ray characterisation of PPN[RuCl4(DMSO)(L1)]·2H2O (1a·2H2O) and PPN[RuCl4(DMSO)(L2)]·3H2O (2a·3H2O), respectively. The two compounds undergo stepwise hydrolytic processes, as assessed by means of UV-vis and 1H NMR spectroscopy. The first hydrolytic step consists of the replacement of a chloride anion with a water molecule, with a half-life of 50 min (1) and 110 min (2), while the subsequent hydrolytic steps are more complicated to describe since more than one product is generated at the same time. The redox potential of the Ru(III)/Ru(II) couple (0.31 V for 1 and 0.28 V for 2) suggests that these complexes can be reduced in the intracellular environment, in agreement with the “activation by reduction” mechanism proposed for NAMI and NAMI-A. 1 and 2 were tested on a human cancer cell line derived from a fibrosarcoma (HT1080), and on non-cancerous primary human fibroblasts (HF), where they showed a modest inhibitory effect.

  合成了两个与抗癌化合物NAMI在结构上相似的铑(III)配合物：Na[RuCl4(DMSO)(L1)] (1)和Na[RuCl4(DMSO)(L2)] (2)，其中L1和L2是不同功能化的噻二嗪-三唑配体。为了促进配合物阴离子的结晶，将Na+替换为[双(triphenylphosphoranylidene)铵]阳离子(PPN+)，从而实现对PPN[RuCl4(DMSO)(L1)]·2H2O (1a·2H2O)和PPN[RuCl4(DMSO)(L2)]·3H2O (2a·3H2O)的X射线表征。这两种化合物经历逐步的水解过程，通过紫外-可见光谱和1H核磁共振光谱进行评估。第一次水解步骤是用水分子替换一个氯离子，半衰期分别为50分钟(1)和110分钟(2)，而后续的水解步骤更复杂，因为同时生成不止一种产物。Ru(III)/Ru(II)对的氧化还原电位(1为0.31 V，2为0.28 V)表明这些配合物可以在细胞内环境中被还原，这与为NAMI和NAMI-A提出的“还原激活”机制相一致。1和2在来自纤维肉瘤(HT1080)的人癌细胞系和非癌性初级人类成纤维细胞(HF)中进行了测试，结果显示出适度的抑制效果。
• RUDNICKA W.; SAWLEWICZ J., ACTA POL. PHARM., 1980, 37, NO 4, 391-396
  作者：RUDNICKA W.、 SAWLEWICZ J.

  DOI：——

  日期：——