(E)-1-(cis-3,4-dihydroxypiperidin-1-yl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(cis-3,4-dihydroxypiperidin-1-yl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
• 英文别名: (E)-1-[(3S,4R)-3,4-dihydroxypiperidin-1-yl]-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
• 化学式: C₁₅H₁₆F₃NO₃
• 分子量: 315.292
• InChiKey: ZSPORYZIHQFYFP-OIOWFRMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(cis-3,4-dihydroxypiperidin-1-yl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、8.0 kPa 条件下， 反应 4.0h， 以85%的产率得到1-(cis-3,4-dihydroxypiperidin-1-yl)-3-(4-(trifluoromethyl)phenyl)propan-1-one
  参考文献：
  名称：

  Synthesis, molecular modeling and evaluation of α-glucosidase inhibition activity of 3,4-dihydroxy piperidines

  摘要：

  Biological evaluation of 3,4-dihydroxy piperidines as alpha-glucosidase inhibitors is being reported for the first time. Forty-five derivatives (amides, di-amides and sulfonamides) were made using cis and trans 3,4-dihydroxy piperidines to evaluate their alpha-glucosidase inhibition activity. Polar groups (-OH, -NH2) on phenyl ring having derivatives 5i, 5l, 7g, 7i & 12j showed excellent activity compared to standard references. Acarbose, Voglibose and Miglitol were used as standard references. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of alpha-glucosidase. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.072
• 作为产物：
  描述：

  1,2,3,6-四氢吡啶 在 盐酸 、 potassium osmate(VI) dihydrate 、 sodium carbonate 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 (E)-1-(cis-3,4-dihydroxypiperidin-1-yl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, molecular modeling and evaluation of α-glucosidase inhibition activity of 3,4-dihydroxy piperidines

  摘要：

  Biological evaluation of 3,4-dihydroxy piperidines as alpha-glucosidase inhibitors is being reported for the first time. Forty-five derivatives (amides, di-amides and sulfonamides) were made using cis and trans 3,4-dihydroxy piperidines to evaluate their alpha-glucosidase inhibition activity. Polar groups (-OH, -NH2) on phenyl ring having derivatives 5i, 5l, 7g, 7i & 12j showed excellent activity compared to standard references. Acarbose, Voglibose and Miglitol were used as standard references. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of alpha-glucosidase. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.072