N-3-methylbenzyl-D-galactonoamidine | 1352436-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-3-methylbenzyl-D-galactonoamidine
• 英文别名: 3-methylbenzyl-D-galactonoamidine；(2R,3S,4S,5S)-2-(hydroxymethyl)-6-[(3-methylphenyl)methylimino]piperidine-3,4,5-triol
• CAS: 1352436-25-9
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: YCCNZNZQZKBAOG-MROQNXINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-methylbenzyl-2,3,4,6-tetra-O-benzyl-D-galactonoamidine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 N-3-methylbenzyl-D-galactonoamidine
  参考文献：
  名称：

  Structure–Activity Relationship of Highly Potent Galactonoamidine Inhibitors toward β-Galactosidase (Aspergillus oryzae)

  摘要：

  A small library of 22 N-substituted galactonoamidines was synthesized, and their structure-activity relationship for inhibition of the hydrolytic activity of beta-galactosidase (Aspergillus oryzae) was evaluated. A fast screening assay in 96-well plate format was used to follow the enzymatic hydrolysis of 2-chloro-4-nitrophenyl-beta-d-galactopyranoside using UV-vis spectroscopy. The aglycon moiety of all compounds was found to have a profound effect on their inhibitory ability. In general, galactonoamidines derived from cyclic aliphatic and linear amines show higher inhibition activity than those derived from benzylamines. Hydrophobic interactions of the methyl group rather than pi-pi stacking interactions of the aromatic ring in p-methylbenzyl-d-galactonoamidine were identified to cause its transition-state-like character and the remarkably high inhibitory ability (K-i = 8 nM). A flexible 3-carbon methylene spacer between the exo N atom of the sugar moiety and a phenyl group furthermore increased the observed apparent inhibition drastically

  DOI：

  10.1021/jm501111y

文献信息

• N-Benzylgalactonoamidines as potent β-galactosidase inhibitors
  作者：Rami Kanso、Elizabeth A. Yancey、Susanne Striegler

  DOI：10.1016/j.tet.2011.10.048

  日期：2012.1

  A series of N-benzylgalactonoamidines was synthesized to probe their inhibitory ability during the hydrolysis of o-nitrophenyl-beta-D-galactopyranoside by beta-galactosidase (Aspergillus oryzae). All compounds are characterized as potent competitive inhibitors with inhibition constants (K-i) in the low nanomolar range (12-48 nM). The structure of the inhibitors mimics the bond-lengthening during the hydrolysis and the aromatic aglycon of the substrate. The electronic nature of the substituent in p-position of the aglycon influences the overall inhibitory ability most when compared to the unsubstituted parent compound. (C) 2011 Elsevier Ltd. All rights reserved.