6-methylthiouridine | 58367-12-7

• 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: 6-methylthiouridine
• 英文别名: 6-methylsulfanyl-uridine；6-Methylthiouridin；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylsulfanylpyrimidine-2,4-dione
• CAS: 58367-12-7
• 化学式: C₁₀H₁₄N₂O₆S
• 分子量: 290.297
• InChiKey: UOAPAWCOFMDTST-XCBZGROMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.13
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  124.78
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-methylthiouridine 在 磷酸三甲酯 、 1,8-双二甲氨基萘 、 三氯氧磷 作用下， 生成 1-[(2R,3R,4S,5R)-5-(dichlorophosphoryloxymethyl)-3,4-dihydroxyoxolan-2-yl]-6-methylsulfanylpyrimidine-2,4-dione
  参考文献：
  名称：

  5-OMe-UDP is a Potent and Selective P2Y₆-Receptor Agonist

  摘要：

  P2Y nucleotide receptors (P2Y-Rs) play Important physiological roles. However, most of the P2Y-R subtypes are still lacking potent and selective agonists and antagonists. Based on data mining analysis of binding interactions in 44 protein-uridine nucleos(t)ides complexes, we designed uracil nucleotides, substituted at the C5/C6 position. All C6-substituted derivatives were inactive at the P2Y(2,4,6)-Rs, while out of the C5-substituted analogues, only 5-OMe-UD(T)P showed activity. To rationalize the data, the ionization and conformation of these analogues were evaluated. The pK(a) values of most analogues Substituted at the C5/C6 positions were unaltered compared to UTP (pK(a) 9.42), except for 5-F-UTP nucleotide (pK(a) 7.85). C6-substituted analogues adopt the syn or high-syn conformations, which are disfavored by the receptors, while 5-OMe-UD(T)P adopt the favored anti. conformation. Furthermore, 5-OMe-UDP adopts the S sugar puckering, which is the conformation preferred by the P2Y(6)-R, but not the P2Y(2)- or P2Y(4)-Rs. 5-OMe-UDP fulfills the conformational and H-bonding requirements of P2Y(6)-R, thus, making a potent P2Y(6)-R agonist (EC50 0.08 mu M), more than UDP (EC50 0.14 mu M).

  DOI：

  10.1021/jm901450d
• 作为产物：
  描述：

  2',3'-O-isopropylidene-5'-O-methoxy-methyl-6-phenylthiouridine 在 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 6-methylthiouridine
  参考文献：
  名称：

  The reaction of 6-phenylthiouridine with sulfur nucleophiles: A simple and regiospecific preparation of 6-alkylthiouridines and 6-alkylthiouridylic acids.

  摘要：

  通过一个区域特异性亲核反应，从相应的 6-苯基硫依啶衍生物合成了 6-烷基硫依啶和 6-烷基硫依啶酸。

  DOI：

  10.1248/cpb.31.1222

文献信息

• PURKAYASTHA, SUBHASISH;MENICHI, GABRIEL;PANZICA, RAYMOND P., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 895-898
  作者：PURKAYASTHA, SUBHASISH、MENICHI, GABRIEL、PANZICA, RAYMOND P.

  DOI：——

  日期：——
• UEHDA, ATSUSI;IGAMI, XIDEHO;TOMIDA, TSUNEHKO
  作者：UEHDA, ATSUSI、IGAMI, XIDEHO、TOMIDA, TSUNEHKO

  DOI：——

  日期：——