4-amino-6-benzyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one | 22285-41-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-amino-6-benzyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one
• 英文别名: 4-amino-6- benzyl-3-(methylthio)-1,2,4-triazin-5(4H)-one；4-amino-6-benzyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one；3-methylthio-4-amino-6-benzyl-1,2,4-triazine-5-one；4-Amino-6-benzyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one；4-amino-6-benzyl-3-methylsulfanyl-1,2,4-triazin-5-one
• CAS: 22285-41-2
• 化学式: C₁₁H₁₂N₄OS
• 分子量: 248.308
• InChiKey: WQGUMNBUPXGXAP-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C(Solv: ethanol (64-17-5))
• 沸点：
  407.1±38.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-6-benzyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one 在 吡啶 、 一水合肼 作用下， 以 异丙醇 为溶剂， 反应 6.0h， 生成 8-amino-6-benzyl-2,8-dihydro-3-thioxo-1,2,4-triazolo[4,3-b][1,2,4]-triazin-7(3H)-one
  参考文献：
  名称：

  Synthesis of Some Novel 6‐Benzyl(or Substituted Benzyl)‐2‐β‐d‐Glucopyranosyl‐1,2,4‐Triazolo[4,3‐b][1,2,4]Triazines as Potential Antimicrobial Chemotherapeutics

  摘要：

  Glucosidation of the new 8-amino-6-benzyl(or substituted benzyl)-2,8-dihydro-1,2,4tri azolo [4,3-b] [1,2,4]triazin-7(3 H)-ones (3a-d) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide 4 gave the corresponding N-glucosides 5a-d. Chemical transformations leading to new functionalities have also been achieved to give compounds 7-12. Antimicrobial activity of compounds 5a-c against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli is described.

  DOI：

  10.1081/ncn-200040663
• 作为产物：
  描述：

  苯丙酮酸 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 4-amino-6-benzyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one
  参考文献：
  名称：

  一些新的1,2,4-三嗪衍生物的合成和杀螨活性

  摘要：

  根据IR，1 H-NMR，13 C-NMR和EI-MS光谱数据设计，合成和鉴定了一系列新的1,2,4-三嗪衍生物。在实验室条件下，评估了1,2,4-三嗪衍生物对卵和Tetranychus urticae（Koch）成年雌性的有效杀螨活性。分析了有前景的1,2,4-三嗪衍生物对卵和成年雌虫的结构杀螨活性关系。取代基的性质和位置对于证明活性很重要。

  DOI：

  10.1002/jhet.3401

文献信息

• Synthesis and structure elucidation of novel fused 1,2,4-triazine derivatives as potent inhibitors targeting CYP1A1 activity
  作者：Abdel Moneim EL Massry、Ahmed Mosaad Asal、Sherine Nabil Khattab、Nesreen Saied Haiba、Hala A. Awney、Mohamed Helmy、Vratislav Langer、Adel Amer

  DOI：10.1016/j.bmc.2012.02.041

  日期：2012.4

  l)-7-oxo-2,3-dihydro-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazine 3d and 2-acetyl-8-(N-acetylamino)-6-benzyl-3-(4-chlorophenyl)-3-methyl-7-oxo-2,3-dihydro-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazine 4e to secure their structures. The inhibitory effect of these compounds toward the CPY1A1 activity was screened to determine their potential as promising anticancer drugs. Our data showed that compounds 4e, 5a

  介绍了新系列的新型1,2,4-三嗪稠合衍生物3a – 3f，4a – 4i和6a – 6b的合成和结构解析及其抑制活性。通过1 H NMR，13 C NMR，MS光谱和元素分析确认了合成化合物的分子结构。对2-乙酰基-8-（N，N-二乙酰氨基）-6-（4-甲氧基苄基）-3-（4-甲氧基-苯基）-7-氧代-2,3-二氢- 7 H- [1,2,4]三唑[4,3- b ] [1,2,4]三嗪3d和2-乙酰基-8-（N-乙酰氨基）-6-苄基-3-（4-氯苯基）-3-甲基-7-氧代-2,3-二氢-7 H- [1,2,4]三唑[4,3- b ] [1 ，2,4]三嗪4e固定其结构。筛选了这些化合物对CPY1A1活性的抑制作用，以确定它们作为有前途的抗癌药物的潜力。我们的数据表明化合物4e，5a，5b和6b在所有测试化合物中具有最高的抑制作用。此外，对三唑三嗪衍生物对接的分析表明，这些化合物仅在蛋白质外
• Khamaev, V. Kh.; Danilov, V. A.; Khannanov, R. N., Russian Journal of Organic Chemistry, 1994, vol. 30, # 5.2, p. 825 - 829
  作者：Khamaev, V. Kh.、Danilov, V. A.、Khannanov, R. N.、Mazitova, A. K.

  DOI：——

  日期：——
• Synthesis, spectroscopic, thermal and biological activity studies on triazine metal complexes
  作者：Gehad G. Mohamed、M.A. Badawy、M.M. Omar、M.M. Nassar、A.B. Kamel

  DOI：10.1016/j.saa.2010.08.002

  日期：2010.11

  The coordination behaviour of the triazine ligand with NNO donation sites, derived from 3-benzyl-7-hydrazinyl-4H-[1,3,4]thiadiazolo[2,3c][1,2,4]triazin-4-one (HL), towards some metal ions namely Mn(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) are reported. The metal complexes are characterized based on elemental analyses, IR. H-1 NMR, solid reflectance, magnetic moment, molar conductance and thermal analyses (TG, DTG and DTA). The ionization constants of the organic ligand under investigation as well as the stability constants of its metal chelates are calculated spectrophotometrically at 25 degrees C. The chelates are found to have octahedral geometrical structures. The ligand (HL) and its binary chelates are subjected to thermal analyses (TG, DTG and DTA) and the different activation thermodynamic parameters are calculated from their corresponding DTG curves to throw more light on the nature of changes accompanying the thermal decomposition process of these compounds. The synthesized ligand and its metal complexes were found to have biological activity against the desert locust Schistocerca gregaria (Forsk.) (Orthoptera - Acrididae) and its adult longevities. (C) 2010 Elsevier B.V. All rights reserved.
• ——
  作者：XIRAI KEHNTARO、 SUGIMOTO XIROXIKO、 MIDZUSITA JOSIO

  DOI：——

  日期：——
• JPS61134389A
  申请人：——

  公开号：JPS61134389A

  公开（公告）日：1986-06-21