(E)-1-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-3-phenylprop-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-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-3-phenylprop-2-en-1-one
• 英文别名: (E)-1-[(3S,4S)-3,4-dihydroxypyrrolidin-1-yl]-3-phenylprop-2-en-1-one
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: XSJGDQTVPSRYCA-KZQRZKTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-3-phenylprop-2-en-1-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、413.69 kPa 条件下， 反应 4.0h， 以90%的产率得到1-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-3-phenylpropan-1-one
  参考文献：
  名称：

  Synthesis and α-glucosidase inhibition activity of dihydroxy pyrrolidines

  摘要：

  A new series of Deacetylsarmentamide A and B derivatives, amides and sulfonamides of 3,4-dihydroxypyrrolidines as alpha-glucosidase inhibitors were designed and synthesized. The biological screening test against alpha-glucosidase showed that some of these compounds have the positive inhibitory activity against alpha-glucosidase. Saturated aliphatic amides were more potent than the olefinic amides. Among all the compounds, 5o/6o having polar -NH2 group, 10f/11f having polar -OH group on phenyl ring displayed 3-4-fold more potent than the standard drugs. Acarbose, Voglibose and Miglitol were used as standard references. The promising compounds 6i, 5o, 6o, 10a, 11a, 10f and 11f have been identified. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of alpha-glucosidase. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.04.078
• 作为产物：
  描述：

  肉桂酸 、 (3S,4S)-吡咯烷-3,4-二醇 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.08h， 以81%的产率得到(E)-1-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Synthesis and α-glucosidase inhibition activity of dihydroxy pyrrolidines

  摘要：

  A new series of Deacetylsarmentamide A and B derivatives, amides and sulfonamides of 3,4-dihydroxypyrrolidines as alpha-glucosidase inhibitors were designed and synthesized. The biological screening test against alpha-glucosidase showed that some of these compounds have the positive inhibitory activity against alpha-glucosidase. Saturated aliphatic amides were more potent than the olefinic amides. Among all the compounds, 5o/6o having polar -NH2 group, 10f/11f having polar -OH group on phenyl ring displayed 3-4-fold more potent than the standard drugs. Acarbose, Voglibose and Miglitol were used as standard references. The promising compounds 6i, 5o, 6o, 10a, 11a, 10f and 11f have been identified. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of alpha-glucosidase. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.04.078

文献信息

• Synthesis and α-glucosidase inhibition activity of dihydroxy pyrrolidines
  作者：Sivaprasad Kasturi、Sujatha Surarapu、Srinivas Uppalanchi、Jaya Shree Anireddy、Shubham Dwivedi、Hasitha Shilpa Anantaraju、Yogeeswari Perumal、Dilep Kumar Sigalapalli、Bathini Nagendra Babu、Krishna S. Ethiraj

  DOI：10.1016/j.bmcl.2017.04.078

  日期：2017.6

  A new series of Deacetylsarmentamide A and B derivatives, amides and sulfonamides of 3,4-dihydroxypyrrolidines as alpha-glucosidase inhibitors were designed and synthesized. The biological screening test against alpha-glucosidase showed that some of these compounds have the positive inhibitory activity against alpha-glucosidase. Saturated aliphatic amides were more potent than the olefinic amides. Among all the compounds, 5o/6o having polar -NH2 group, 10f/11f having polar -OH group on phenyl ring displayed 3-4-fold more potent than the standard drugs. Acarbose, Voglibose and Miglitol were used as standard references. The promising compounds 6i, 5o, 6o, 10a, 11a, 10f and 11f have been identified. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of alpha-glucosidase. (C) 2017 Elsevier Ltd. All rights reserved.