4-Benzyl-3-benzylsulfanyl-5-methyl-1,2,4-triazole | 1012073-37-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-Benzyl-3-benzylsulfanyl-5-methyl-1,2,4-triazole
• CAS: 1012073-37-8
• 化学式: C₁₇H₁₇N₃S
• 分子量: 295.408
• InChiKey: CRJNANOWZMGYGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴甲苯 、 4-苄基-5-甲基-4H-[1,2,4]噻唑-3-硫醇 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 生成 4-Benzyl-3-benzylsulfanyl-5-methyl-1,2,4-triazole
  参考文献：
  名称：

  Triazole derivatives as non-nucleoside inhibitors of HIV-1 reverse transcriptase—Structure–activity relationships and crystallographic analysis

  摘要：

  A series of 3,4,5-trisubstituted 1,2,4-4H triazole derivatives was synthesized and investigated for HIV-1 reverse transcriptase inhibition. An X-ray structure with HIV-1 RT secured the binding mode and allowed the key interactions with the enzyme to be identified.

  DOI：

  10.1016/j.bmcl.2007.11.127

文献信息

• Certain triazole-based compounds, compositions, and uses thereof
  申请人：Hodge Nicholas Carl

  公开号：US20050288347A1

  公开（公告）日：2005-12-29

  Thiotriazole-based chemical entities exhibiting ATP-utilizing enzyme inhibitory activity, methods of using such chemical entities, and compositions comprising such chemical entities, are described.

  描述了具有 ATP 利用酶抑制活性的硫代三唑类化学实体、使用此类化学实体的方法以及包含此类化学实体的组合物。
• Searching for novel scaffold of triazole non-nucleoside inhibitors of HIV-1 reverse transcriptase
  作者：Tomasz Frączek、Agata Paneth、Rafał Kamiński、Agnieszka Krakowiak、Piotr Paneth

  DOI：10.3109/14756366.2015.1039531

  日期：——

  Azoles are a promising class of the new generation of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). From thousands of reported compounds, many possess the same basic structure of an aryl substituted azole ring linked by a thioglycolamide chain with another aromatic ring. In order to find novel extensions for this basic scaffold, we explored the 5-position substitution pattern of triazole NNRTIs using molecular docking followed by the synthesis of selected compounds. We found that heterocyclic substituents in the 5-position of the triazole ring are detrimental to the inhibitory activity of compounds with four-membered thioglycolamide linker and this substitution seems to be viable only for compounds with shorter two-membered linker. Promising compound, N-(4-carboxy-2-chlorophenyl)-2-((4-benzyl-5-methyl-4H-1,2,4-triazol-3-yl)sulfanyl)acetamide, with potent inhibitory activity and acceptable aqueous solubility has been identified in this study that could serve as lead scaffold for the development of novel water-soluble salts of triazole NNRTIs.