4-氟-3-(1-吡咯烷羰基)苯硼酸 | 874219-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氟-3-(1-吡咯烷羰基)苯硼酸
• 中文别名: 4-氟-3-(吡咯啉-1-羰基)苯基硼酸
• 英文名称: 4-Fluoro-3-(pyrrolidine-1-carbonyl)phenylboronic acid
• 英文别名: [4-fluoro-3-(pyrrolidine-1-carbonyl)phenyl]boronic acid
• CAS: 874219-31-5
• 化学式: C₁₁H₁₃BFNO₃
• 分子量: 237.039
• InChiKey: AOICJNUBSAKHMW-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154
• 沸点：
  462.0±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-氟-3-(1-吡咯烷羰基)苯硼酸 、 3-bromo-5-(methylsulfonyl)-4H-1,2,4-triazole 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 [2-fluoro-5-(5-methylsulfonyl-1H-1,2,4-triazol-3-yl)phenyl]-pyrrolidin-1-ylmethanone
  参考文献：
  名称：

  1,2,4-Triazolsulfone: A novel isosteric replacement of acylsulfonamides in the context of Na V 1.7 inhibition

  摘要：

  Recently, the identification of several classes of aryl sulfonamides and acyl sulfonamides that potently inhibit Na(v)1.7 and demonstrate high levels of selectivity over other Na-v isoforms have been reported. The fully ionizable nature of these inhibitors has been shown to be an important part of the pharmacophore for the observed potency and isoform selectivity. The requirement of this functionality, however, has presented challenges associated with optimization toward inhibitors with drug-like properties and minimal off-target activity. In an effort to obviate these challenges, we set out to develop an orally bioavailable, selective Na(v)1.7 inhibitor, lacking these acidic functional groups. Herein, we report the discovery of a novel series of inhibitors wherein a triazolesulfone has been designed to serve as a bioisostere for the acyl sulfonamide. This work culminated in the delivery of a potent series of inhibitors which demonstrated good levels of selectivity over Na v 1.5 and favorable pharmacokinetics in rodents. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.04.035