α-D-galactose-1-phosphate tributylamine salt | 1228316-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-galactose-1-phosphate tributylamine salt
• CAS: 1228316-87-7
• 化学式: C₆H₁₃O₉P*C₁₂H₂₇N
• 分子量: 445.491
• InChiKey: QRAKZZNBMIVWOQ-NNQFXEKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  29.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  160.15
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  α-D-galactose-1-phosphate tributylamine salt 、 三乙胺氢溴酸盐 、 5-iodouridine 5'-monophosphomorpholidate 在 四氮唑 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 以69 mg的产率得到5-iodouridine-5'-diphosphate-α-D-galactose triethylammonium
  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