2',3',5'-tri-O-benzoyl-5-n-propyluridine | 72503-96-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2',3',5'-tri-O-benzoyl-5-n-propyluridine
• 英文别名: 2',3',5'-Tri-O-benzoyl-5-propyluracil；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(2,4-dioxo-5-propylpyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 72503-96-9
• 化学式: C₃₃H₃₀N₂O₉
• 分子量: 598.609
• InChiKey: QCBUDZNFWBHGNI-LTGLEFCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  142.99
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-benzoyl-5-n-propyluridine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 5-Propyluridin
  参考文献：
  名称：

  5-Substituted UTP derivatives as P2Y2 receptor agonists

  摘要：

  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.

  DOI：

  10.1016/s0223-5234(99)00211-1
• 作为产物：
  描述：

  5-n-propyl-cytidine 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 以90%的产率得到2',3',5'-tri-O-benzoyl-5-n-propyluridine
  参考文献：
  名称：

  Synthetic nucleosides and nucleotides. XXVIII. Synthesis of 5-alkylcytidines from 5-alkylbarbituric acids.

  摘要：

  5-烷基巴比妥酸（1b-f）在N,N-二乙基苯胺盐酸盐存在下，使用磷酰氯在回流的正丁基乙酸酯中转化为5-烷基-2,4,6-三氯嘧啶（2b-f）。将2与甲氧基钠在干燥乙腈中处理，随后与乙基硫醇钾反应并在Raney Ni存在下脱硫，得到本研究的关键中间体5-烷基-2,4-二甲氧基嘧啶（5b-f）。在乙腈中锡氯存在下，将5与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖反应，定量得到5-烷基-1-(2,3,5-三-O-苯甲酰基)-β-D-呋喃核糖基-1,2-二氢-4-甲氧基嘧啶-2-酮（6a-f）。用甲醇氨处理6得到标题5-烷基胞嘧啶核苷（7a-f）。化合物6也很容易通过与盐酸处理转化为相应的尿嘧啶核苷。还研究了7对培养的小鼠白血病L5178Y细胞的生长抑制作用、对培养的CHSE-214细胞中的传染性造血坏死病毒（IHNV）的抗病毒活性以及作为人胞嘧啶脱氨酶底物的性质。

  DOI：

  10.1248/cpb.36.2673

文献信息

• SANEYOSHI, MINEO;WATANABE, SHINICHI, CHEM. AND PHARM. BULL., 36,(1988) N 7, C. 2673-2678
  作者：SANEYOSHI, MINEO、WATANABE, SHINICHI

  DOI：——

  日期：——