(2R,4aR,6S,7R,8R,8aS)-6-(((3-hydroxy-4-methoxybenzyl)amino)methyl)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol | 1450752-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aR,6S,7R,8R,8aS)-6-(((3-hydroxy-4-methoxybenzyl)amino)methyl)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 1450752-00-7
• 化学式: C₂₂H₂₇NO₇
• 分子量: 417.459
• InChiKey: LLICMQMVNLBJBH-NXOOKBFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  109.64
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,7R,8R,8aS)-6-(((3-hydroxy-4-methoxybenzyl)amino)methyl)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 在 水 、 溶剂黄146 作用下， 反应 1.0h， 生成 N-(β-D-glucopyranosylmethyl)-3-hydroxy-4-methoxybenzylamine
  参考文献：
  名称：

  Synthesis and α-glucosidase inhibitory activity evaluation of N-substituted aminomethyl-β-d-glucopyranosides

  摘要：

  A series of N-substituted 1-aminomethyl-beta-D-glucopyranoside derivatives was prepared. These novel synthetic compounds were assessed in vitro for inhibitory activity against yeast a-glucosidase and both rat intestinal a-glucosidases maltase and sucrase. Most of the compounds displayed a-glucosidase inhibitory activity, with IC50 values covering the wide range from 2.3 mu M to 2.0 mM. Compounds 19a (IC50 = 2.31 mu M) and 19b (IC50 = 5.6 mu M) were identified as the most potent inhibitors for yeast a-glucosidase, while compounds 16 (IC50 = 7.7 and 15.6 mu M) and 19e (IC50 = 5.1 and 10.4 mu M) were the strongest inhibitors of rat intestinal maltase and sucrase. Analysis of the kinetics of enzyme inhibition indicated that 19e inhibited maltase and sucrase in a competitive manner. The results suggest that the aminomethyl-beta-o-glucopyranoside moiety can mimic the substrates of a-glucosidase in the enzyme catalytic site, leading to competitive enzyme inhibition. Moreover, the nature of the N-substituent has considerable influence on inhibitory potency. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.002
• 作为产物：
  描述：

  4,6-O-benzylidene-D-glucose 在 palladium 10% on activated carbon 、 甲酸铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 51.5h， 生成 (2R,4aR,6S,7R,8R,8aS)-6-(((3-hydroxy-4-methoxybenzyl)amino)methyl)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
  参考文献：
  名称：

  Synthesis and α-glucosidase inhibitory activity evaluation of N-substituted aminomethyl-β-d-glucopyranosides

  摘要：

  A series of N-substituted 1-aminomethyl-beta-D-glucopyranoside derivatives was prepared. These novel synthetic compounds were assessed in vitro for inhibitory activity against yeast a-glucosidase and both rat intestinal a-glucosidases maltase and sucrase. Most of the compounds displayed a-glucosidase inhibitory activity, with IC50 values covering the wide range from 2.3 mu M to 2.0 mM. Compounds 19a (IC50 = 2.31 mu M) and 19b (IC50 = 5.6 mu M) were identified as the most potent inhibitors for yeast a-glucosidase, while compounds 16 (IC50 = 7.7 and 15.6 mu M) and 19e (IC50 = 5.1 and 10.4 mu M) were the strongest inhibitors of rat intestinal maltase and sucrase. Analysis of the kinetics of enzyme inhibition indicated that 19e inhibited maltase and sucrase in a competitive manner. The results suggest that the aminomethyl-beta-o-glucopyranoside moiety can mimic the substrates of a-glucosidase in the enzyme catalytic site, leading to competitive enzyme inhibition. Moreover, the nature of the N-substituent has considerable influence on inhibitory potency. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.002