5-(aminosulfonyl)-2-[(3,4-difluorophenyl)thio]-N-(4-methoxybenzyl)nicotinamide | 1232772-78-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(aminosulfonyl)-2-[(3,4-difluorophenyl)thio]-N-(4-methoxybenzyl)nicotinamide
• 英文别名: 2-(3,4-difluorophenyl)sulfanyl-N-[(4-methoxyphenyl)methyl]-5-sulfamoylpyridine-3-carboxamide
• CAS: 1232772-78-9
• 化学式: C₂₀H₁₇F₂N₃O₄S₂
• 分子量: 465.501
• InChiKey: LZNQOLHEWHQXON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  ethyl 5-(aminosulfonyl)-2-[(3,4-difluorophenyl)thio]nicotinate 、 4-甲氧基苄胺 在 三甲基铝 、 盐酸 作用下， 以 四氢呋喃 、 甲苯 、 甲醇 、 水 为溶剂， 反应 25.0h， 以69%的产率得到5-(aminosulfonyl)-2-[(3,4-difluorophenyl)thio]-N-(4-methoxybenzyl)nicotinamide
  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.