5-(2-furyl)-UDP-α-D-galactose | 1356191-49-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5-(2-furyl)-UDP-α-D-galactose
• CAS: 1356191-49-5
• 化学式: C₆H₁₅N*C₁₉H₂₆N₂O₁₈P₂
• 分子量: 733.557
• InChiKey: MVJKIZPRIJNYKI-KZKKDTJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.19
• 重原子数：
  48.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  313.37
• 氢给体数：
  9.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  5-iodouridine-5′-monophosphate 在 四氮唑 、 sodium tetrachloropalladate(II) 、 trisodium tris(3-sulfophenyl)phosphine 、 caesium carbonate 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.66h， 生成 5-(2-furyl)-UDP-α-D-galactose
  参考文献：
  名称：

  Inhibition of Galactosyltransferases by a Novel Class of Donor Analogues

  摘要：

  Galactosyltransferases (GalT) are important molecular targets in a range of therapeutic areas, including infection, inflammation, and cancer. GalT inhibitors are therefore sought after as potential lead compounds for drug discovery. We have recently discovered a new class of GalT inhibitors with a novel mode of action. In this publication, we describe a series of analogues which provide insights, for the first time, into SAR for this new mode of GalT inhibition. We also report that a new C-glycoside, designed as a chemically stable analogue of the most potent inhibitor in this series, retains inhibitory activity against a panel of GalTs. Initial results from cellular studies suggest that despite their polarity, these sugar-nucleotides are taken up by HL-60 cells. Results from molecular modeling studies with a representative bacterial GalT provide a rationale for the differences in bioactivity observed in this series. These findings may provide a blueprint for the rational development of new GalT inhibitors with improved potency.

  DOI：

  10.1021/jm201154p