(3S,4R)-4-(2,5-difluorophenyl)-6-oxopiperidine-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3S,4R)-4-(2,5-difluorophenyl)-6-oxopiperidine-3-carboxylic acid
• 化学式: C₁₂H₁₁F₂NO₃
• 分子量: 255.221
• InChiKey: DBIHJXBLOHUNJF-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 盐酸 、 platinum(IV) oxide 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (3S,4R)-4-(2,5-difluorophenyl)-6-oxopiperidine-3-carboxylic acid 、 (3R,4R)-4-(2,5-difluorophenyl)-6-oxopiperidine-3-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel aminomethyl-piperidones based DPP-IV inhibitors

  摘要：

  A series of novel aminomethyl-piperidones were designed and evaluated as potential DPP-IV inhibitors. Optimized analogue 12v ((4S, 5S)-5-(aminomethyl)-1-(2-(benzo[d][1,3] dioxol-5-yl) ethyl)-4-(2,5-difluorophenyl) piperidin-2-one) showed excellent in vitro potency and selectivity for DPP-IV over other serine proteases. The lead compound 12v showed potent and long acting antihyperglycemic effects (in vivo), along with improved pharmacokinetic profile. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.009

文献信息

• Design, synthesis and biological evaluation of novel aminomethyl-piperidones based DPP-IV inhibitors
  作者：Pradip Jadav、Rajesh Bahekar、Shailesh R. Shah、Dipam Patel、Amit Joharapurkar、Mukul Jain、Kalapatapu V.V.M. Sairam、Praveen Kumar Singh

  DOI：10.1016/j.bmcl.2014.03.009

  日期：2014.4

  A series of novel aminomethyl-piperidones were designed and evaluated as potential DPP-IV inhibitors. Optimized analogue 12v ((4S, 5S)-5-(aminomethyl)-1-(2-(benzo[d][1,3] dioxol-5-yl) ethyl)-4-(2,5-difluorophenyl) piperidin-2-one) showed excellent in vitro potency and selectivity for DPP-IV over other serine proteases. The lead compound 12v showed potent and long acting antihyperglycemic effects (in vivo), along with improved pharmacokinetic profile. (c) 2014 Elsevier Ltd. All rights reserved.