(2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol | 1101869-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
• CAS: 1101869-65-1
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: SSDYDQSJZPPXNQ-HUXSOILUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  91.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol 在 palladium dihydroxide 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 以95%的产率得到(2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol
  参考文献：
  名称：

  Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library

  摘要：

  Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A ( 20) and B ( 18) against alpha-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 mu M, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.063
• 作为产物：
  描述：

  (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(3,4-dimethoxyphenyl)pyrrolidin-1-ol 在 盐酸 、 palladium dihydroxide 、 水 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以87%的产率得到(2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
  参考文献：
  名称：

  Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library

  摘要：

  Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A ( 20) and B ( 18) against alpha-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 mu M, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.063

文献信息

• Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library
  作者：En-Lun Tsou、Sih-Yu Chen、Ming-Hsun Yang、Shih-Chi Wang、Ting-Ren Rachel Cheng、Wei-Chieh Cheng

  DOI：10.1016/j.bmc.2008.10.063

  日期：2008.12.15

  Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A ( 20) and B ( 18) against alpha-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 mu M, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases. (C) 2008 Elsevier Ltd. All rights reserved.