N-(4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzylidene)methoxyamine | 950762-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzylidene)methoxyamine
• CAS: 950762-11-5
• 化学式: C₂₂H₂₇NO₁₁
• 分子量: 481.456
• InChiKey: OXLRMRDQILKNCS-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145.25
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  甲氧基胺盐酸盐 、 4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 N-(4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzylidene)methoxyamine
  参考文献：
  名称：

  Discovery of 4-functionalized phenyl-O-β-d-glycosides as a new class of mushroom tyrosinase inhibitors

  摘要：

  A series of 4-functionalized phenyl-O-beta-D-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that compounds 6a-13a bearing a thiosemicarbazide moiety exhibited potent activities with IC50 values range from 0.31 to 52.8 mu M. Particularly, compound 9a containing acetylated glucose moiety was found to be the most active molecule with an IC50 value of 0.31 mu M. SARs analysis suggested that (1) the thiosemicarbazide moiety remarkably contributed to the increase of inhibitory effects on tyrosinase; (2) the configuration and bond type of sugar moiety also played a very important role in determining their inhibitory activities. The inhibition kinetics and inhibition mechanism study revealed that compound 9a was reversible and competitive type inhibitor, whereas compound 13a was reversible and competitive-uncompetitive mixed-II type inhibitor. (c) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.09.018

文献信息

• Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors
  作者：Huan Wen、Chonglan Lin、Ling Que、Hui Ge、Lin Ma、Rihui Cao、Yiqian Wan、Wenlie Peng、Zihou Wang、Huacan Song

  DOI：10.1016/j.ejmech.2007.03.018

  日期：2008.1

  A series of helicid analogues were prepared and evaluated in vitro for the cholinesterase (AChE and BuChE) inhibitory activities via UV spectroscopy. The results indicated that compounds 5, 6d and 8 exhibited potent AChE inhibitory activities with IC50 values of 0.45 +/- 0.02 mu M 0.49 +/- 0.02 mu M, and 0.20 +/- 0.01 mu M, respectively. High selectivity for AChE over BuChE was also observed. Kinetic study showed that the mechanism of AChE inhibition of compounds 5, 6d and 8 was all mixed-type. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Discovery of 4-functionalized phenyl-O-β-d-glycosides as a new class of mushroom tyrosinase inhibitors
  作者：Wei Yi、Rihui Cao、Huan Wen、Qin Yan、Binhua Zhou、Lin Ma、Huacan Song

  DOI：10.1016/j.bmcl.2009.09.018

  日期：2009.11

  A series of 4-functionalized phenyl-O-beta-D-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that compounds 6a-13a bearing a thiosemicarbazide moiety exhibited potent activities with IC50 values range from 0.31 to 52.8 mu M. Particularly, compound 9a containing acetylated glucose moiety was found to be the most active molecule with an IC50 value of 0.31 mu M. SARs analysis suggested that (1) the thiosemicarbazide moiety remarkably contributed to the increase of inhibitory effects on tyrosinase; (2) the configuration and bond type of sugar moiety also played a very important role in determining their inhibitory activities. The inhibition kinetics and inhibition mechanism study revealed that compound 9a was reversible and competitive type inhibitor, whereas compound 13a was reversible and competitive-uncompetitive mixed-II type inhibitor. (c) 2009 Published by Elsevier Ltd.