(1R,2S,3R,4R,5R)-8-butyl-4-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-1,2,3-triol | 1279128-77-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (1R,2S,3R,4R,5R)-8-butyl-4-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-1,2,3-triol
• 英文别名: n-butyl noeurostegine
• CAS: 1279128-77-6
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: QWJDIYVWDIRBLX-MTVMDMGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1R,2S,3R,4R,5R)-2,3-di-O-benzyl-4-C-benzyloxymethyl-8-butyl-8-azabicyclo[3.2.1]octane-1-ol 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以89%的产率得到(1R,2S,3R,4R,5R)-8-butyl-4-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-1,2,3-triol
  参考文献：
  名称：

  Synthesis of N-alkylated noeurostegines and evaluation of their potential as treatment for Gaucher’s disease

  摘要：

  The potent and selective inhibitor of beta-glucosidases, noeurostegine, was evaluated as an inhibitor of glucocerebrosidase (GCase) to give an IC50 value of 0.4 mu M, being 250- and 150-fold better than N-butyl and N-nonyl noeurostegine, respectively. The parent noeurostegine and its N-butyl and N-nonyl alkylated congeners were also tested as pharmacological chaperones against a N370S GCase mutant. Of these, only noeurostegine, was found to increase enzyme activity, which in potency was comparable to that previously reported for isofagomine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.106

文献信息

• Synthesis of N-alkylated noeurostegines and evaluation of their potential as treatment for Gaucher’s disease
  作者：Tina S. Rasmussen、Sarah Allman、Gabriele Twigg、Terry D. Butters、Henrik H. Jensen

  DOI：10.1016/j.bmcl.2010.12.106

  日期：2011.3

  The potent and selective inhibitor of beta-glucosidases, noeurostegine, was evaluated as an inhibitor of glucocerebrosidase (GCase) to give an IC50 value of 0.4 mu M, being 250- and 150-fold better than N-butyl and N-nonyl noeurostegine, respectively. The parent noeurostegine and its N-butyl and N-nonyl alkylated congeners were also tested as pharmacological chaperones against a N370S GCase mutant. Of these, only noeurostegine, was found to increase enzyme activity, which in potency was comparable to that previously reported for isofagomine. (C) 2011 Elsevier Ltd. All rights reserved.