(3aS,4S,6aR)-4-(5-(1-(2-hydroxybenzyl)-1H-1,2,3-triazol-4-yl)pentyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并咪唑类化合物
• 英文名称: (3aS,4S,6aR)-4-(5-(1-(2-hydroxybenzyl)-1H-1,2,3-triazol-4-yl)pentyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one
• 英文别名: (3aS,4S,6aR)-4-[5-[1-[(2-hydroxyphenyl)methyl]triazol-4-yl]pentyl]-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-2-one
• 化学式: C₁₉H₂₅N₅O₂S
• 分子量: 387.506
• InChiKey: DEPVTLXNPGJWFY-SZMVWBNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  水杨醇 在 四氯化碳 、 sodium azide 、 三苯基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 (3aS,4S,6aR)-4-(5-(1-(2-hydroxybenzyl)-1H-1,2,3-triazol-4-yl)pentyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one
  参考文献：
  名称：

  New Series of BPL Inhibitors To Probe the Ribose-Binding Pocket of Staphylococcus aureus Biotin Protein Ligase

  摘要：

  Replacing the labile adenosinyl-substituted phosphoanhydride of biotinyl-5'-AMP with a N1-benzyl substituted 1,2,3-triazole gave a new truncated series of inhibitors of Staphylococcus aureus biotin protein ligase (SaBPL). The benzyl group presents to the ribose-binding pocket of SaBPL based on in silico docking. Halogenated benzyl derivatives (12t, 12u, 12w, and 12x) proved to be the most potent inhibitors of SaBPL. These derivatives inhibited the growth of S. aureus ATCC49775 and displayed low cytotoxicity against HepG2 cells.

  DOI：

  10.1021/acsmedchemlett.6b00248

文献信息

• New Series of BPL Inhibitors To Probe the Ribose-Binding Pocket of <i>Staphylococcus aureus</i> Biotin Protein Ligase
  作者：Jiage Feng、Ashleigh S. Paparella、William Tieu、David Heim、Sarah Clark、Andrew Hayes、Grant W. Booker、Steven W. Polyak、Andrew D. Abell

  DOI：10.1021/acsmedchemlett.6b00248

  日期：2016.12.8

  Replacing the labile adenosinyl-substituted phosphoanhydride of biotinyl-5'-AMP with a N1-benzyl substituted 1,2,3-triazole gave a new truncated series of inhibitors of Staphylococcus aureus biotin protein ligase (SaBPL). The benzyl group presents to the ribose-binding pocket of SaBPL based on in silico docking. Halogenated benzyl derivatives (12t, 12u, 12w, and 12x) proved to be the most potent inhibitors of SaBPL. These derivatives inhibited the growth of S. aureus ATCC49775 and displayed low cytotoxicity against HepG2 cells.