Bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)methane | 223753-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)methane
• 英文别名: BAMTM；4-amino-3-[(4-amino-5-sulfanylidene-1H-1,2,4-triazol-3-yl)methyl]-1H-1,2,4-triazole-5-thione
• CAS: 223753-21-7
• 化学式: C₅H₈N₈S₂
• 分子量: 244.304
• InChiKey: XCNDSQCYMPUZIM-UHFFFAOYSA-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  Bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)methane 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
  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：

  丙二酸 、 硫代卡巴肼 反应 0.5h， 以80%的产率得到Bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)methane
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1039/a808351g

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
• Studies on some N-bridged heterocycles derived from bis-[4-amino-5-mercapto-1,2,4-triazol-3-yl] alkanes
  作者：B Shivarama Holla、Richard Gonsalves、Shalini Shenoy

  DOI：10.1016/s0014-827x(98)00068-8

  日期：1998.8

  A series of bis-[4-amino-5-mercapto-1,2,4-triazol-3-yl] alkanes have been synthesized and were converted into bis-[1,2,4-triazolo[3,4-b]-1,3,4-thiadiazol-4-yl] alkanes. The newly synthesized compounds were characterized by analytical IR, NMR and mass spectral studies. Some of the newly synthesized compounds were screened for their antibacterial properties and exhibited activity with MIC in the range 3-12.5 micrograms/ml.
• Holla; Gonsalves, Bollettino Chimico Farmaceutico, 1998, vol. 137, # 11, p. 467 - 472
  作者：Holla、Gonsalves

  DOI：——

  日期：——
• Antimicrobial and DNA-Cleavage Studies of 22-Membered N₄Tetraaza Macrocyclic Triazoles: Template Synthesis and Physicochemical Characterization
  作者：Sangamesh A. Patil、Udaykumar V. Kamble、Prema S. Badami

  DOI：10.1080/15257770.2010.504600

  日期：2010.8.13

  A novel series of 22-membered macrocyclic complexes of the type [MLCl2] (M=Co2+, Ni2+ and Cu2+) have been synthesized with newly derived biologically active ligands (L1-LIV). These ligands were synthesized by the condensation of ortho-phthalaldehyde and bis-(4-amino-5-mercapto-1, 2, 4-triazole-3-yl)alkanes. The mode of bonding and overall geometry of the complexes have been inferred through IR, EPR, electronic spectral studies, conductivity, magnetic, thermal, and electrochemical studies. All these complexes have been screened for their antibacterial (Escherichia coli, Staphylococus aureus, Salmonella typhi, Pseudomonas aeruginosa) and antifungal activities (Aspergillus niger, Aspergillus flavus, and Cladosporium) by the minimal inhibitory concentration (MIC) method. The DNA cleavage study was done by agarose gel electrophoresis technique.