biotin hydrazide | 88193-59-3

• 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: biotin hydrazide
• 英文别名: 6-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]hexanehydrazide
• CAS: 88193-59-3
• 化学式: C₁₁H₂₀N₄O₂S
• 分子量: 272.371
• InChiKey: DBXXFFZFKCXPTP-NRPADANISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  biotin hydrazide 、 5-(5-methyl-2-oxo-1,3-benzoxazol-3-yl)pentanimidate hydrochloride 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以21%的产率得到3-[4-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentyl]-1,3,4-oxadiazol-2-yl]butyl]-5-methyl-1,3-benzoxazol-2-one
  参考文献：
  名称：

  Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase

  摘要：

  Inhibitors of Staphylococcus aureus biotin protein ligase (SaBPL) are generated by replacing the acyl phosphate group of biotinyl-5'-AMP with either a 1,2,3-triazole (see 5/10a/10b) or a 1,2,4-oxadiazole (see 7) bioisostere. Importantly, the inhibitors are inactive against the human BPL. The nature of the 5-substituent in the component benzoxazolone of the optimum 1,2,3-triazole series is critical to activity, where this group binds in the ATP binding pocket of the enzyme.

  DOI：

  10.1016/j.bmcl.2014.08.030
• 作为产物：
  描述：

  D-homobiotin 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 biotin hydrazide
  参考文献：
  名称：

  Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase

  摘要：

  Inhibitors of Staphylococcus aureus biotin protein ligase (SaBPL) are generated by replacing the acyl phosphate group of biotinyl-5'-AMP with either a 1,2,3-triazole (see 5/10a/10b) or a 1,2,4-oxadiazole (see 7) bioisostere. Importantly, the inhibitors are inactive against the human BPL. The nature of the 5-substituent in the component benzoxazolone of the optimum 1,2,3-triazole series is critical to activity, where this group binds in the ATP binding pocket of the enzyme.

  DOI：

  10.1016/j.bmcl.2014.08.030

文献信息

• [EN] NOVEL ANTIMICROBIAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIMICROBIENS
  申请人：ADELAIDE RES & INNOVATION PTY

  公开号：WO2013040647A1

  公开（公告）日：2013-03-28

  A new class of biotin protein ligase (BPL) inhibitors that have antibacterial activity against multiple Staphylococcus aureus isolates, including clinically important methicillin-resistant S. aureus (MRSA) are disclosed that are non-toxic.

  披萨店的招牌菜是各种口味的披萨，包括经典的意大利香肠披萨、夏威夷披萨、墨西哥辣椒披萨等。
• NOVEL ANTIMICROBIAL COMPOUNDS
  申请人：MONASH UNIVERSITY

  公开号：US20140296177A1

  公开（公告）日：2014-10-02

  A new class of biotin protein ligase (BPL) inhibitors that have antibacterial activity against multiple Staphylococcus aureus isolates, including clinically important methicillin-resistant S. aureus (MRSA) are disclosed that are non-toxic.

  披露了一种新型生物素蛋白连接酶（BPL）抑制剂，对包括临床重要的甲氧西林耐药金黄色葡萄球菌（MRSA）在内的多种金黄色葡萄球菌具有抗菌活性，并且是无毒的。
• US9108978B2
  申请人：——

  公开号：US9108978B2

  公开（公告）日：2015-08-18
• Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase
  作者：William Tieu、Angie M. Jarrad、Ashleigh S. Paparella、Kelly A. Keeling、Tatiana P. Soares da Costa、John C. Wallace、Grant W. Booker、Steven W. Polyak、Andrew D. Abell

  DOI：10.1016/j.bmcl.2014.08.030

  日期：2014.10

  Inhibitors of Staphylococcus aureus biotin protein ligase (SaBPL) are generated by replacing the acyl phosphate group of biotinyl-5'-AMP with either a 1,2,3-triazole (see 5/10a/10b) or a 1,2,4-oxadiazole (see 7) bioisostere. Importantly, the inhibitors are inactive against the human BPL. The nature of the 5-substituent in the component benzoxazolone of the optimum 1,2,3-triazole series is critical to activity, where this group binds in the ATP binding pocket of the enzyme.