[2-(α-D-galactopyranosyl)-ethylphosphono]-5-iodouridin-5-yl' phosphate | 1286201-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(α-D-galactopyranosyl)-ethylphosphono]-5-iodouridin-5-yl' phosphate
• 英文别名: [[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-iodo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-[2-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]ethyl]phosphinic acid
• CAS: 1286201-92-0
• 化学式: C₁₇H₂₇IN₂O₁₆P₂
• 分子量: 704.257
• InChiKey: WHKUEMXUIBEMEZ-FQBVKVBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  282
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [2-(α-D-galactopyranosyl)-ethylphosphono]-5-iodouridin-5-yl' phosphate 、 5-醛基-2-噻吩硼酸 在 sodium tetrachloropalladate(II) 水 、 caesium carbonate 、 三乙胺 作用下， 反应 2.0h， 以59%的产率得到bis(sodium) [2-(α-D-galactopyranosyl)-ethylphosphono]-5(5-formylthien-2-y)-uridin-5-yl' phosphate
  参考文献：
  名称：

  [EN] DERIVATIVES OF URIDINE PHOSPHATE AND THEIR USES IN PROTEIN BINDING ASSAYS
  [FR] COMPOSÉS ET LEURS UTILISATIONS DANS DES DOSAGES DE LIAISON AUX PROTÉINES

  摘要：

  公开号：

  WO2011051733A3
• 作为产物：
  描述：

  尿苷5-单磷酸 在 四氮唑 、 碘 、 硝酸 作用下， 以 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.08h， 生成 [2-(α-D-galactopyranosyl)-ethylphosphono]-5-iodouridin-5-yl' phosphate
  参考文献：
  名称：

  [EN] DERIVATIVES OF URIDINE PHOSPHATE AND THEIR USES IN PROTEIN BINDING ASSAYS
  [FR] COMPOSÉS ET LEURS UTILISATIONS DANS DES DOSAGES DE LIAISON AUX PROTÉINES

  摘要：

  公开号：

  WO2011051733A3

文献信息

• Inhibition of Galactosyltransferases by a Novel Class of Donor Analogues
  作者：Karine Descroix、Thomas Pesnot、Yayoi Yoshimura、Sebastian S. Gehrke、Warren Wakarchuk、Monica M. Palcic、Gerd K. Wagner

  DOI：10.1021/jm201154p

  日期：2012.3.8

  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.