(2S,3R,5R)-2-(2,5-difluorophenyl)-5-(4,6-dihydro-1H-pyrrolo[3,4-c]pyrazol-5-yl)oxan-3-amine | 1456616-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡唑类
• 英文名称: (2S,3R,5R)-2-(2,5-difluorophenyl)-5-(4,6-dihydro-1H-pyrrolo[3,4-c]pyrazol-5-yl)oxan-3-amine
• CAS: 1456616-65-1
• 化学式: C₁₆H₁₈F₂N₄O
• 分子量: 320.342
• InChiKey: JFUBTJMMAHQVJI-XFJVYGCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-二氟苯甲酰氯 在 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 rhodium(III) chloride 、 癸硼烷 、 sodium hydride 、 N,N-二异丙基乙胺 、 锌 作用下， 以 甲醇 、 乙醇 、 正己烷 、 水 、 乙酸乙酯 为溶剂， 生成 (2S,3R,5R)-2-(2,5-difluorophenyl)-5-(4,6-dihydro-1H-pyrrolo[3,4-c]pyrazol-5-yl)oxan-3-amine
  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.