N-(4-hydroxy-3-methoxybenzyl)-epi-aminoquercitol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4-hydroxy-3-methoxybenzyl)-epi-aminoquercitol
• 英文别名: (1R,2S,3S,4S,5S)-5-[(4-hydroxy-3-methoxyphenyl)methylamino]cyclohexane-1,2,3,4-tetrol
• 化学式: C₁₄H₂₁NO₆
• 分子量: 299.324
• InChiKey: QDYWCXOLUPJDDX-QBWSDTANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  122
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  原栎醇 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 15-冠醚-5 、 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 N-(4-hydroxy-3-methoxybenzyl)-epi-aminoquercitol
  参考文献：
  名称：

  N-Arylmethylaminoquercitols, a new series of effective antidiabetic agents having α-glucosidase inhibition and antioxidant activity

  摘要：

  A new series of N-arylalkylaminoquercitols were synthesized by reductive amination of aminoquercitol bisacetonide 5 and a variety of aryl aldehydes. The targeted N-substituted aminoquercitols having phenolic moiety (7a-7c) displayed significantly enhanced alpha-glucosidase inhibition, which is 26-32 times more potent than that of the unmodified aminoquercitol 6. In addition, compounds 7a-7c also retained antioxidant activity with relatively more pronounced potency than their original phenolics. This recent finding suggests an approach to develop effective antidiabetic agents by incorporating antioxidative moiety into aminocyclitol core structure. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.033

文献信息

• N-Arylmethylaminoquercitols, a new series of effective antidiabetic agents having α-glucosidase inhibition and antioxidant activity
  作者：Wisuttaya Worawalai、Sumrit Wacharasindhu、Preecha Phuwapraisirisan

  DOI：10.1016/j.bmcl.2015.04.033

  日期：2015.6

  A new series of N-arylalkylaminoquercitols were synthesized by reductive amination of aminoquercitol bisacetonide 5 and a variety of aryl aldehydes. The targeted N-substituted aminoquercitols having phenolic moiety (7a-7c) displayed significantly enhanced alpha-glucosidase inhibition, which is 26-32 times more potent than that of the unmodified aminoquercitol 6. In addition, compounds 7a-7c also retained antioxidant activity with relatively more pronounced potency than their original phenolics. This recent finding suggests an approach to develop effective antidiabetic agents by incorporating antioxidative moiety into aminocyclitol core structure. (C) 2015 Elsevier Ltd. All rights reserved.