(2S,3S)-3-N-(tert-butoxycarbonyl)amino-2-(4-bromophenyl)-4-(3-fluoroazetidin-1-yl)-N,N-dimethyl-4-oxobutanamide | 899429-07-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-3-N-(tert-butoxycarbonyl)amino-2-(4-bromophenyl)-4-(3-fluoroazetidin-1-yl)-N,N-dimethyl-4-oxobutanamide
• 英文别名: tert-butyl N-[(2S,3S)-3-(4-bromophenyl)-4-(dimethylamino)-1-(3-fluoroazetidin-1-yl)-1,4-dioxobutan-2-yl]carbamate
• CAS: 899429-07-3
• 化学式: C₂₀H₂₇BrFN₃O₄
• 分子量: 472.354
• InChiKey: PTYVDDSXLCFEOP-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-N-(tert-butoxycarbonyl)amino-2-(4-bromophenyl)-4-(3-fluoroazetidin-1-yl)-N,N-dimethyl-4-oxobutanamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 生成 (2S,3S)-3-Amino-4-(3-fluoro-azetidin-1-yl)-N,N-dimethyl-4-oxo-2-(4-[1,2,4]triazolo[1,5-a]pyridin-6-yl-phenyl)-butyramide; compound with trifluoro-acetic acid
  参考文献：
  名称：

  (2S,3S)-3-Amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-(4-[1,2,4]triazolo[1,5-a]- pyridin-6-ylphenyl)butanamide:  A Selective α-Amino Amide Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes

  摘要：

  A series of beta-substituted biarylphenylalanine amides were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-4) for the treatment of type 2 diabetes. Optimization of the metabolic profile of early analogues led to the discovery of (2S,3S)-3-amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2(4-[1,2,4] triazolo[1,5-a]pyridin-6-ylphenyl)butanamide (6), a potent, orally active DPP-4 inhibitor (IC50 = 6.3 nM) with excellent selectivity, oral bioavailability in preclinical species, and in vivo efficacy in animal models. Compound 6 was selected for further characterization as a potential new treatment for type 2 diabetes.

  DOI：

  10.1021/jm060015t
• 作为产物：
  描述：

  (2S,3S)-2-(4-Bromo-phenyl)-3-tert-butoxycarbonylamino-4-(3-fluoro-azetidin-1-yl)-4-oxo-butyric acid 、 二甲胺 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3S)-3-N-(tert-butoxycarbonyl)amino-2-(4-bromophenyl)-4-(3-fluoroazetidin-1-yl)-N,N-dimethyl-4-oxobutanamide
  参考文献：
  名称：

  (2S,3S)-3-Amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-(4-[1,2,4]triazolo[1,5-a]- pyridin-6-ylphenyl)butanamide:  A Selective α-Amino Amide Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes

  摘要：

  A series of beta-substituted biarylphenylalanine amides were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-4) for the treatment of type 2 diabetes. Optimization of the metabolic profile of early analogues led to the discovery of (2S,3S)-3-amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2(4-[1,2,4] triazolo[1,5-a]pyridin-6-ylphenyl)butanamide (6), a potent, orally active DPP-4 inhibitor (IC50 = 6.3 nM) with excellent selectivity, oral bioavailability in preclinical species, and in vivo efficacy in animal models. Compound 6 was selected for further characterization as a potential new treatment for type 2 diabetes.

  DOI：

  10.1021/jm060015t