2-phenylethyl α-D-mannopyranoside | 134733-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenylethyl α-D-mannopyranoside
• 英文别名: ethylphenyl α-D-mannoside；(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-phenylethoxy)oxane-3,4,5-triol
• CAS: 134733-76-9
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: MLRIJUWUQTVDQE-DGTMBMJNSA-N

物化性质

• 沸点：
  486.8±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-phenylethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 在 甲醇 、 sodium methylate 作用下， 以86%的产率得到2-phenylethyl α-D-mannopyranoside
  参考文献：
  名称：

  FimH Antagonists for the Oral Treatment of Urinary Tract Infections: From Design and Synthesis to in Vitro and in Vivo Evaluation

  摘要：

  Urinary tract infection (UTI) by uropathogenic Escherichia coli (UPEC) is one of the most common infections, particularly affecting women. The interaction of FimH, a lectin located at the tip of bacterial pill, with high mannose structures is critical for the ability of UPEC to colonize and invade the bladder epithelium. We describe the synthesis and the in vitro/in vivo evaluation of alpha-D-mannosides with the ability to block the bacteria/host cell interaction. According to the pharmacokinetic properties, a prodrug approach for their evaluation in the UTI mouse model was explored. As a result, an orally available, low molecular weight FimH antagonist was identified with the potential to reduce the colony forming units (CFU) in the urine by 2 orders of magnitude and in the bladder by 4 orders of magnitude. With FimH antagonist 16b, the great potential for the effective treatment of urinary tract infections with a new class of orally available antiinfectives could be demonstrated.

  DOI：

  10.1021/jm101011y

文献信息

• Interactions of aromatic mannosyl disulfide derivatives with Concanavalin A: synthesis, thermodynamic and NMR spectroscopy studies
  作者：Bandaru Narasimha Murthy、Sharmistha Sinha、Avadhesha Surolia、Narayanaswamy Jayaraman、László Szilágyi、Ildikó Szabó、Katalin E. Kövér

  DOI：10.1016/j.carres.2009.06.008

  日期：2009.9

  alpha-D-Mannopyranosyl units were attached to an aromatic scaffold through disulfide linkages to obtain mono- to trivalent glycosylated ligands for lectin binding studies. Isothermal titration calorimetric (ITC) measurements indicated that binding affinities of these derivatives to Concanavalin A (Con A) were comparable to or slightly higher than that of methyl alpha-D-mannopyranoside (K(a) values in the range of

  通过二硫键将α-D-甘露吡喃糖基单元连接到芳香族骨架上，以获得用于凝集素结合研究的单价至三价糖基化配体。等温滴定热法（ITC）测量表明，这些衍生物与伴刀豆球蛋白A（Con A）的结合亲和力与甲基α-D-甘露吡喃糖苷（K（a）值在10（4）范围内）相当或稍高。 M（-1））。凝集素-配体配合物的化学计量与相应配体的形式价（1-3）一致，表明与二价和三价衍生物相互作用时发生交联。但是，后者无法观察到多价效应。使用饱和转移差异（STD）NMR竞争实验显示，这些配体与Con A的碳水化合物结合位点结合。
• Irani, Rustom K; Sinha, Bharati; Bose, J L, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 5, p. 519 - 521
  作者：Irani, Rustom K、Sinha, Bharati、Bose, J L

  DOI：——

  日期：——
• FimH Antagonists for the Oral Treatment of Urinary Tract Infections: From Design and Synthesis to in Vitro and in Vivo Evaluation
  作者：Tobias Klein、Daniela Abgottspon、Matthias Wittwer、Said Rabbani、Janno Herold、Xiaohua Jiang、Simon Kleeb、Christine Lüthi、Meike Scharenberg、Jacqueline Bezençon、Erich Gubler、Lijuan Pang、Martin Smiesko、Brian Cutting、Oliver Schwardt、Beat Ernst

  DOI：10.1021/jm101011y

  日期：2010.12.23

  Urinary tract infection (UTI) by uropathogenic Escherichia coli (UPEC) is one of the most common infections, particularly affecting women. The interaction of FimH, a lectin located at the tip of bacterial pill, with high mannose structures is critical for the ability of UPEC to colonize and invade the bladder epithelium. We describe the synthesis and the in vitro/in vivo evaluation of alpha-D-mannosides with the ability to block the bacteria/host cell interaction. According to the pharmacokinetic properties, a prodrug approach for their evaluation in the UTI mouse model was explored. As a result, an orally available, low molecular weight FimH antagonist was identified with the potential to reduce the colony forming units (CFU) in the urine by 2 orders of magnitude and in the bladder by 4 orders of magnitude. With FimH antagonist 16b, the great potential for the effective treatment of urinary tract infections with a new class of orally available antiinfectives could be demonstrated.