2,5-Difluorobenzoic acid, phenyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2,5-Difluorobenzoic acid, phenyl ester
• 英文别名: phenyl 2,5-difluorobenzoate
• 化学式: C₁₃H₈F₂O₂
• 分子量: 234.202
• InChiKey: BGYKTOQZECZEJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-Difluorobenzoic acid, phenyl ester 在 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 rhodium(III) chloride 、 sodium hydride 、 锌 作用下， 以 乙醇 、 正己烷 、 水 为溶剂， 生成 N-[(2R,3S)-2-(2,5-二氟苯基)四氢-5-氧代-2H-吡喃-3-基]氨基甲酸叔丁酯
  参考文献：
  名称：

  Novel tetrahydropyran analogs as dipeptidyl peptidase IV inhibitors: Profile of clinical candidate (2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-amine (23)

  摘要：

  A series of novel tri-2,3,5-substituted tetrahydropyran analogs were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-4) for the treatment of type 2 diabetes. Optimization of the series provided inhibitors with good DPP-4 potency and selectivity over other peptidases (QPP, DPP8, and FAP). Compound 23, which is very potent, selective, efficacious in the diabetes PD model, and has an excellent pharmacokinetic profile, is selected as a clinical candidate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.061
• 作为产物：
  描述：

  2,5-二氟苯甲酰氯 、 苯酚 在 N,N-二异丙基乙胺 作用下， 生成 2,5-Difluorobenzoic acid, phenyl ester
  参考文献：
  名称：

  Novel tetrahydropyran analogs as dipeptidyl peptidase IV inhibitors: Profile of clinical candidate (2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-amine (23)

  摘要：

  A series of novel tri-2,3,5-substituted tetrahydropyran analogs were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-4) for the treatment of type 2 diabetes. Optimization of the series provided inhibitors with good DPP-4 potency and selectivity over other peptidases (QPP, DPP8, and FAP). Compound 23, which is very potent, selective, efficacious in the diabetes PD model, and has an excellent pharmacokinetic profile, is selected as a clinical candidate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.061

文献信息

• Novel tetrahydropyran analogs as dipeptidyl peptidase IV inhibitors: Profile of clinical candidate (2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-amine (23)
  作者：Tesfaye Biftu、Xiaoxia Qian、Ping Chen、Dennis Feng、Giovanna Scapin、Ying-Duo Gao、Jason Cox、Ranabir Sinha Roy、George Eiermann、Huabing He、Kathy Lyons、Gino Salituro、Sangita Patel、Alexander Petrov、Feng Xu、Shiyao Sherrie Xu、Bei Zhang、Charles Caldwell、Joseph K. Wu、Kathy Lyons、Ann E. Weber

  DOI：10.1016/j.bmcl.2013.07.061

  日期：2013.10

  A series of novel tri-2,3,5-substituted tetrahydropyran analogs were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-4) for the treatment of type 2 diabetes. Optimization of the series provided inhibitors with good DPP-4 potency and selectivity over other peptidases (QPP, DPP8, and FAP). Compound 23, which is very potent, selective, efficacious in the diabetes PD model, and has an excellent pharmacokinetic profile, is selected as a clinical candidate. (C) 2013 Elsevier Ltd. All rights reserved.