O2',O3'-hydroxyphosphoryl-5-methyl-uridine | 47139-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: O2',O3'-hydroxyphosphoryl-5-methyl-uridine
• 英文别名: O^2'_,O3'-hydroxyphosphoryl-5-methyl-uridine；Ribothymidin-monophosphorsaeureester-(2'.3')；5-Methyl-uridin-2',3'-cyclophosphat
• CAS: 47139-37-7
• 化学式: C₁₀H₁₃N₂O₈P
• 分子量: 320.196
• InChiKey: KSMPIBRAFJECKV-JXOAFFINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.38
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  140.08
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  5-甲基尿甙 在 三氯氧磷 、 水 作用下， 反应 12.5h， 生成 O2',O3'-hydroxyphosphoryl-5-methyl-uridine 、 Thymidin-5'-monophosphat
  参考文献：
  名称：

  Fully Automated Continuous Meso-flow Synthesis of 5′-Nucleotides and Deoxynucleotides

  摘要：

  The first continuous meso-flow synthesis of natural and non-natural 5'-nucleotides and deoxynucleotides is described, representing a significant advance over the corresponding in-flask method. By means of this meso-flow technique, a synthesis with time consumption and high-energy consumption becomes facile to generate products with great efficiency. An abbreviated duration, satisfactory output, and mild reaction conditions are expected to be realized under the present procedure.

  DOI：

  10.1021/op5002066

文献信息

• 5-Substituted UTP derivatives as P2Y2 receptor agonists
  作者：B Knoblauch

  DOI：10.1016/s0223-5234(99)00211-1

  日期：1999.10

  A series of 5-alkyl-substituted UTP derivatives, which had been synthesized previously with a moderate degree of purity, was resynthesized, purified, and characterized. Synthetic and purification procedures were optimized. New spectroscopic data, including C-13- and P-31 NMR data, are presented. Phosphorylation reactions yielded a number of side products, such as the 2'-, 3'-, and 5'-monophosphates, the 2',3'-cyclic monophosphates, and the 2',3'-cyclic phosphates of the 5'-triphosphates. Furthermore, raw products were contaminated with inorganic phosphates, including cyclometatriphosphate, phosphate, and pyrophosphate. The uracil nucleotides were investigated for their potency to increase intracellular calcium concentrations by stimulation of P2Y(2) receptors (P2Y(2)R) on NG108-15 cells, a mouse neuroblastoma x glioma cell line, and in human basal epithelial airway cells, including a cystic fibrosis (CF/T43) cell line. UTP exhibited EC50 values of ca. 1 mu M (in NG108-15 cells) and of 0.1 mu M (in CF/T43 cells), respectively. 5-Substituted UTP derivatives were agonists at the P2Y(2)R, but were less potent than UTP. 5-Ethyl-UTP, for example, exhibited an EC50 value of 99 mu M at P2Y(2)R of NG108-15 cells and proved to be a full agonist. With increasing volume of the 5-substituent of UTP derivatives, P2Y(2) activity decreased. (C) 1999 Editions scientifiques et medicales Elsevier SAS.