2,6-difluoro-3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazol-2-yl]methoxy}benzamide | 951123-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-difluoro-3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazol-2-yl]methoxy}benzamide
• 英文别名: 2,6-Difluoro-3-[[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazol-2-yl]methoxy]benzamide
• CAS: 951123-11-8
• 化学式: C₂₁H₂₁BF₂N₂O₄S
• 分子量: 446.283
• InChiKey: YQYFLHXBEONOOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-碘咪唑 、 2,6-difluoro-3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazol-2-yl]methoxy}benzamide 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以2 mg的产率得到3-{[5-(1H-imidazol-2-yl)-1,3-benzothiazol-2-yl]methoxy}-2,6-difluorobenzamide
  参考文献：
  名称：

  Creating an Antibacterial with in Vivo Efficacy: Synthesis and Characterization of Potent Inhibitors of the Bacterial Cell Division Protein FtsZ with Improved Pharmaceutical Properties

  摘要：

  3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.

  DOI：

  10.1021/jm9016366
• 作为产物：
  描述：

  3-[(5-bromo-1,3-benzothiazol-2-yl)methoxy]-2,6-difluorobenzamide 、 联硼酸频那醇酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium acetate 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 2,6-difluoro-3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazol-2-yl]methoxy}benzamide
  参考文献：
  名称：

  Creating an Antibacterial with in Vivo Efficacy: Synthesis and Characterization of Potent Inhibitors of the Bacterial Cell Division Protein FtsZ with Improved Pharmaceutical Properties

  摘要：

  3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.

  DOI：

  10.1021/jm9016366

文献信息

• Creating an Antibacterial with in Vivo Efficacy: Synthesis and Characterization of Potent Inhibitors of the Bacterial Cell Division Protein FtsZ with Improved Pharmaceutical Properties
  作者：David J. Haydon、James M. Bennett、David Brown、Ian Collins、Greta Galbraith、Paul Lancett、Rebecca Macdonald、Neil R. Stokes、Pramod K. Chauhan、Jignesh K. Sutariya、Narendra Nayal、Anil Srivastava、Joy Beanland、Robin Hall、Vincent Henstock、Caterina Noula、Chris Rockley、Lloyd Czaplewski

  DOI：10.1021/jm9016366

  日期：2010.5.27

  3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.