(3r,4r,5r)-3,4-Dihydroxy-5-({[(1r)-2-Hydroxy-1-Phenylethyl]amino}methyl)-1-Methylpyrrolidin-2-One | 1067243-69-9

• 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: (3r,4r,5r)-3,4-Dihydroxy-5-({[(1r)-2-Hydroxy-1-Phenylethyl]amino}methyl)-1-Methylpyrrolidin-2-One
• 英文别名: (3R,4R,5R)-3,4-dihydroxy-5-[[[(1R)-2-hydroxy-1-phenylethyl]amino]methyl]-1-methylpyrrolidin-2-one
• CAS: 1067243-69-9
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: DNDCXXSXVWBCJF-UMSGYPCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3aR,6S,6aR)-2,2,5-trimethyl-4-oxo-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-6-carbaldehyde 、 D-苯甘氨醇 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以22 mg的产率得到(3r,4r,5r)-3,4-Dihydroxy-5-({[(1r)-2-Hydroxy-1-Phenylethyl]amino}methyl)-1-Methylpyrrolidin-2-One
  参考文献：
  名称：

  Functionalized pyrrolidine inhibitors of human type II α-mannosidases as anti-cancer agents: Optimizing the fit to the active site

  摘要：

  Refining the chemical structure of functionalized pyrrolidine-based inhibitors of Golgi alpha-mannosidase II (GMII) to optimize binding affinity provided a lead molecule that demonstrated nanomolar competitive inhibition of alpha-mannosidases II and an optimal fit in the active site of Drosophila GMII by X-ray crystallography. Esters of this lead compound also inhibited the growth of human glioblastoma and brain-derived endothelial cells more than the growth of non-tumoral human fibroblasts, suggesting their potential for anti-cancer therapy.

  DOI：

  10.1016/j.bmc.2008.06.021