5-(aminosulfonyl)-2-fluoro-N-(2-methoxyethyl)benzamide | 1232686-26-8

• 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: 5-(aminosulfonyl)-2-fluoro-N-(2-methoxyethyl)benzamide
• 英文别名: 2-fluoro-N-(2-methoxyethyl)-5-sulfamoylbenzamide
• CAS: 1232686-26-8
• 化学式: C₁₀H₁₃FN₂O₄S
• mdl: MFCD21101914
• 分子量: 276.289
• InChiKey: NTZDPSFIKJFZDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-苯乙硫醇 、 5-(aminosulfonyl)-2-fluoro-N-(2-methoxyethyl)benzamide 在 caesium carbonate 、 盐酸 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 2.0h， 以100%的产率得到5-(aminosulfonyl)-N-(2-methoxyethyl)-2-[(2-phenylethyl)thio]benzamide
  参考文献：
  名称：

  Thioether benzenesulfonamide inhibitors of carbonic anhydrases II and IV: Structure-based drug design, synthesis, and biological evaluation

  摘要：

  A novel series of potent thioether benzenesulfonamide inhibitors of carbonic anhydrases II and IV was discovered using structure-based drug design. Synthesis, structure-activity relationship, and optimization of physicochemical properties are described. Low nanomolar potency was achieved, and selected compounds with improved thermodynamic solubility showed promising in vitro inhibition of carbonic anhydrase activity in rabbit iris ciliary body homogenate.

  DOI：

  10.1016/j.bmc.2010.03.014
• 作为产物：
  描述：

  2-氟-5-磺酰胺基-苯甲酸 、 2-甲氧基乙胺 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以58%的产率得到5-(aminosulfonyl)-2-fluoro-N-(2-methoxyethyl)benzamide
  参考文献：
  名称：

  Thioether benzenesulfonamide inhibitors of carbonic anhydrases II and IV: Structure-based drug design, synthesis, and biological evaluation

  摘要：

  A novel series of potent thioether benzenesulfonamide inhibitors of carbonic anhydrases II and IV was discovered using structure-based drug design. Synthesis, structure-activity relationship, and optimization of physicochemical properties are described. Low nanomolar potency was achieved, and selected compounds with improved thermodynamic solubility showed promising in vitro inhibition of carbonic anhydrase activity in rabbit iris ciliary body homogenate.

  DOI：

  10.1016/j.bmc.2010.03.014

文献信息

• Thioether benzenesulfonamide inhibitors of carbonic anhydrases II and IV: Structure-based drug design, synthesis, and biological evaluation
  作者：William Vernier、Wesley Chong、David Rewolinski、Samantha Greasley、Thomas Pauly、Morena Shaw、Dac Dinh、Rose Ann Ferre、Seiji Nukui、Martha Ornelas、Eric Reyner

  DOI：10.1016/j.bmc.2010.03.014

  日期：2010.5

  A novel series of potent thioether benzenesulfonamide inhibitors of carbonic anhydrases II and IV was discovered using structure-based drug design. Synthesis, structure-activity relationship, and optimization of physicochemical properties are described. Low nanomolar potency was achieved, and selected compounds with improved thermodynamic solubility showed promising in vitro inhibition of carbonic anhydrase activity in rabbit iris ciliary body homogenate.