p-methoxyphenyl 3-O-propargyl-β-D-galactopyranoside | 1196990-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3-O-propargyl-β-D-galactopyranoside
• CAS: 1196990-39-2
• 化学式: C₁₆H₂₀O₇
• 分子量: 324.331
• InChiKey: PDMLGRCARWMWFV-DGADGQDISA-N

物化性质

• 沸点：
  553.3±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.47
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.61
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3-O-propargyl-β-D-galactopyranoside 在 吡啶 、 copper(l) iodide 、 对甲苯磺酰叠氮 、 乙酰溴 、 四丁基氟化铵 、 sodium methylate 、 三乙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 54.5h， 生成 5,6-bis(fluoranyl)-3-[[(2~{S},3~{R},4~{S},5~{S},6~{R})-2-[(2~{S},3~{R},4~{S},5~{R},6~{R})-4-[4-(3-fluorophenyl)-1,2,3-triazol-1-yl]-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-2-yl]sulfanyl-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-4-yl]oxymethyl]chromen-2-one
  参考文献：
  名称：

  Systematic Tuning of Fluoro-galectin-3 Interactions Provides Thiodigalactoside Derivatives with Single-Digit nM Affinity and High Selectivity

  摘要：

  Symmetrical and asymmetrical fluorinated phenyltriazolyl-thiodigalactoside derivatives have been synthesized and evaluated as inhibitors of galectin-1 and galectin-3. Systematic tuning of the phenyltriazolyl-thiodigalactosides' fluoro-interactions with galectin-3 led to the discovery of inhibitors with exceptional affinities (K-d down to 1-2 nM) in symmetrically substituted thiodigalactosides as well as unsurpassed combination of high affinity (K-d 7.5 nM) and selectivity (46-fold) over galectin-1 for asymmetrical thiodigalactosides by carrying one trifluorphenyltriazole and one coumaryl moiety. Studies of the inhibitor-galectin complexes with isothermal titration calorimetry and X-ray crystallography revealed the importance of fluoro-amide interaction for affinity and for selectivity. Finally, the high affinity of the discovered inhibitors required two competitive titration assay tools to be developed: a new high affinity fluorescent probe for competitive fluorescent polarization and a competitive ligand optimal for analyzing high affinity galectin-3 inhibitors with competitive isothermal titration calorimetry.

  DOI：

  10.1021/acs.jmedchem.7b01626
• 作为产物：
  描述：

  3-溴丙炔 、 4-甲氧基苯基-Β-D-半乳糖苷 在 二正丁基氧化锡 、 四丁基碘化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 22.0h， 以80%的产率得到p-methoxyphenyl 3-O-propargyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Neu5Ac-Gal-functionalized gold glyconanoparticles

  摘要：

  Neu5Ac-Gal-containing neoglycoside 1 was convergently synthesized through Cu(I)-catalyzed 1,3-dipolar cycloaddition of methyl (6-azidohexyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-O-alpha-D-glycero-D-galacto-2-nonulopyranosyl)uronate and 11-thioacetylundecyl 2,4,6-tri-O-benzoyl-3-O-propargyl-beta-D-galactopyranoside. The stable and water-soluble gold glyconanoparticle 2 (d = 3.4 nm) has been successfully prepared from neoglycoside 1 and characterized by NMR, IR, and TEM techniques. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.06.039