4-amino-3-[3-(4-amino-5-sulfanylidene-1H-1,2,4-triazol-3-yl)propyl]-1H-1,2,4-triazole-5-thione | 225117-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-3-[3-(4-amino-5-sulfanylidene-1H-1,2,4-triazol-3-yl)propyl]-1H-1,2,4-triazole-5-thione
• CAS: 225117-37-3
• 化学式: C₇H₁₂N₈S₂
• 分子量: 272.358
• InChiKey: AAGFTMXXXIBLMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-3-[3-(4-amino-5-sulfanylidene-1H-1,2,4-triazol-3-yl)propyl]-1H-1,2,4-triazole-5-thione 在 碳酸氢钠 作用下， 以 氯仿 、 双氧水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.67h， 生成 bis-[6-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazol-4-yl]propane
  参考文献：
  名称：

  Synthesis and Anticancer Activity of Bis-(N-Glucosylated Triazolothiadiazolyl) Alkanes via Cyclocondensation Reaction Involving C–s and C–n Bond formation

  摘要：

  A series of bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl) alkanes have been synthesized and were condensed with N-tetra-O-acetyl--D-glucopyranosyl isocyanodichloride to afford biologically active bis-[6-tetra-O-acetyl--D-glucopyranosylimino-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazol-4-yl] alkanes. The structures of the new glucosylated heterocyclic compounds have been established by IR, H-1 NMR, and C-13 NMR spectroscopy, and mass spectrometry analyses. Among the synthesized compounds, a few target compounds were screened for their in vitroanticancer activity against two human cancer cell lines, viz. MCF-7 (Breast) and HEPG2 (Liver).

  DOI：

  10.1080/10426507.2015.1083570
• 作为产物：
  描述：

  戊二酸 、 硫代卡巴肼 以72%的产率得到4-amino-3-[3-(4-amino-5-sulfanylidene-1H-1,2,4-triazol-3-yl)propyl]-1H-1,2,4-triazole-5-thione
  参考文献：
  名称：

  Regioselective synthesis of novel N-aminotriazolophanes

  摘要：

  双[4-氨基-1,2,4-三唑]是由二元酸和硫代氨基脲通过芳香族酸肼与水合肼和二硫化碳缩合而制备的。在甲醇水溶液中，这些双[4-氨基-1,2,4-三唑]在氢氧化钾存在下与 1,ω-二卤代烃发生区域选择性烷基化反应，得到了新型 N-氨基三唑烷。对这些 N-氨基三唑烷的立体化学和抗菌活性进行了研究。在三唑烷 5h、8d 和 8f 中，观察到两个 N-NH2 基团互为反式，而在其他三唑烷中，观察到两个 N-NH2 基团互为顺式：4-氨基-1,2,4-三唑，1,ω-二卤代烃，S-烷基化，区域选择性，N-氨基三唑烷。

  DOI：

  10.1139/v06-181

文献信息

• 2-Bromo-1-(1H-pyrazol-4-yl)ethanone: versatile precursors for novel mono-, bis- and poly{6-(1H-pyrazol-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines}
  作者：Mostafa E. Salem、Ahmed F. Darweesh、Ahmad M. Farag、Ahmed H.M. Elwahy

  DOI：10.1016/j.tet.2015.12.024

  日期：2016.2

  A simple synthesis of novel mono-, bis- and poly6-(1H-pyrazol-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines} is reported. The formation of the target compounds was achieved by the reaction of 2-bromo-1-(5-methyl-1-phenyl-1H-pyrazol-4-yl)ethanone with the appropriate aminotriazolethiol or by the reaction of 6-pyrazolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-3-thiol with the appropriate di- and

  新型单，双和聚6-（1 H-吡唑-4-基）-[1,2,4]三唑[3,4- b ] [1,3,4]噻二嗪的简单合成被报道。通过2-溴-1-（5-甲基-1-苯基-1 H-吡唑-4-基）乙酮与适当的氨基三唑硫醇的反应或6-吡唑基-的反应实现目标化合物的形成。7 H- [1,2,4]三唑并[3,4- b ] [1,3,4]噻二嗪-3-硫醇与适当的二-和聚（溴）化合物。通过光谱和元素分析确定了新合成化合物的结构。
• Synthesis of novel scaffolds based on thiazole or triazolothiadiazine linked to benzofuran or benzo[<i>d</i>]thiazole moieties as new hybrid molecules
  作者：Mostafa E. Salem、Ahmed F. Darweesh、Ahmed H. M. Elwahy

  DOI：10.1080/00397911.2019.1694689

  日期：2020.1.17

  Abstract A synthesis of novel hybrid molecules containing thiazole or bis(thiazoles) each bearing benzofuran and/or benzo[d]thiazole moieties by the reaction of the appropriate thioamide derivatives with the corresponding bis-bromoacetyl derivatives is reported. Mono- and bis(triazolothiadiazine) derivatives based on benzofuran or benzo[d]thiazole moieties were also synthesized in good yields by the

  摘要 报道了通过适当的硫代酰胺衍生物与相应的双溴乙酰基衍生物反应合成含有噻唑或双（噻唑）的新型杂化分子，每个分子带有苯并呋喃和/或苯并[d]噻唑部分。基于苯并呋喃或苯并[d]噻唑部分的单和双（三唑噻二嗪）衍生物也通过适当的双（溴乙酰基）衍生物与4-氨基-5-巯基-1,2、 4-三唑及其相应的双衍生物。图形概要
• Synthesis of a Novel Class of Azacrown Macrocycles and Lariat Crown Ethers Containing Two 1,2,4-Triazole Rings as Subunits
  作者：Naser Foroughifar、Akbar Mobinikhaledi、Sattar Ebrahimi

  DOI：10.1055/s-0029-1217398

  日期：2009.8

  prepared in 70-76% yield by the condensation reaction of 1,2-, 1,3-, and 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)alkanes with bisaldehydes in acetic acid under reflux. Reaction of two of these azacrown macrocycles with iodomethane and benzyl chloride furnished exclusively the target lariat macrocycles in good yields. azacrown macrocycles - 1,2,4-triazole - thiols - bistri­azoles - lariat crown

  通过1,2-，1,3-和1,4-双（4-氨基-5-巯基-4 H -1,2,4-三唑的缩合反应，制备Azacrown大环化合物，收率为70-76％-3-基）烷烃与双醛在乙酸中回流。这些两个氮杂皇冠大环与碘甲烷和苄基氯的反应以高收率完全提供了目标套索大环。 氮杂皇冠大环-1,2,4-三唑-硫醇-双三唑-套索冠醚
• A Facile Synthesis of Bis(4-amino-5-mercapto-1,2,4-triazol-3-yl)alkanes and Bis(5-mercapto-4H-1,2,4-triazol-3-yl)alkanes
  作者：Peng-Fei Xu、Xiao-Wen Sun、Lin-Mei Zhang、Zi-Yi Zhang

  DOI：10.1039/a808351g

  日期：——

  The facile preparation of bis(4-amino-5-mercapto-1,2,4-triazol-3-yl)alkanes 1a–d and bis(5-mercapto-4H-1,2,4-triazol-3-yl)alkanes 2a–d in one-step is described.

  描述了一种一步法简便合成双(4-氨基-5-巯基-1,2,4-三唑-3-基)烷烃 1a–d 和双(5-巯基-4H-1,2,4-三唑-3-基)烷烃 2a–d 的方法。
• Synthesis of new aza crown macrocycles and lariat ethers
  作者：Sattar Ebrahimi、Hassan Moghanian

  DOI：10.1515/hc-2011-0058

  日期：2012.2.1

  yield by condensation reaction of 1,3- and 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)alkanes 1a,b with bis-aldehydes 2a,b. Reactions of 3a,b with methyl or benzyl iodide furnished the target lariat ethers 4a–d.

  摘要 通过1,3-和1,4-双(4-氨基-5-巯基-4H-1,2,4-三唑-3-基)烷烃的缩合反应，以良好的收率合成了氮杂冠大环3a,b。 1a,b 与双醛 2a,b。3a,b 与甲基碘或苄基碘的反应提供了目标套索醚 4a-d。