3-fluorobenzyl-2,3,4,6-tetra-O-benzyl-D-galactonoamidine | 1352436-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-fluorobenzyl-2,3,4,6-tetra-O-benzyl-D-galactonoamidine
• 英文别名: m-fluorobenzyl-2,3,4,6-tetra-O-benzyl-D-galactonoamidine
• CAS: 1352436-22-6
• 化学式: C₄₁H₄₁FN₂O₄
• 分子量: 644.786
• InChiKey: ILTRSYISOWREOM-ROZBJHDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  48.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  61.31
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-fluorobenzyl-2,3,4,6-tetra-O-benzyl-D-galactonoamidine 在 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以95%的产率得到N-3-fluorobenzyl-D-galactonoamidine
  参考文献：
  名称：

  评估 N-苄基半乳糖脒作为 β-半乳糖苷水解的假定过渡态类似物†

  摘要：

  实验证据提供了一种用于p -methylbenzyl- d -galactonoamidine到功能如对芳基-β-的酶水解的真实过渡态类似物d通过β半乳糖苷酶（-galactopyranosides米曲霉）。对于选择的底物，该化合物在低纳摩尔浓度范围 (12–56 nM) 内表现出抑制常数。沿着这些思路，优化了基于相转移催化的简化合成方法，以提供所需的各种新型芳基-β - D-吡喃半乳糖苷。最后，证实了半乳糖脒在测定条件下的稳定性。

  DOI：

  10.1039/c4ob00153b
• 作为产物：
  描述：

  (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)piperidin-2-one 在 劳森试剂 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 3-fluorobenzyl-2,3,4,6-tetra-O-benzyl-D-galactonoamidine
  参考文献：
  名称：

  N-Benzylgalactonoamidines as potent β-galactosidase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.10.048

文献信息

• Structure–Activity Relationship of Highly Potent Galactonoamidine Inhibitors toward β-Galactosidase (<i>Aspergillus oryzae</i>)
  作者：Qiu-Hua Fan、Kailey A. Claunch、Susanne Striegler

  DOI：10.1021/jm501111y

  日期：2014.11.13

  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