α-(Ξ)-oxiranyl-[5']thymidylic acid

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: α-(Ξ)-oxiranyl-[5']thymidylic acid
• 英文别名: 5-(Ξ)-oxiranylmethyl-2'-deoxy-[5']uridylic acid；[(2R,3S,5R)-3-hydroxy-5-[5-(oxiran-2-ylmethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate
• 化学式: C₁₂H₁₇N₂O₉P
• 分子量: 364.249
• InChiKey: VIYUNHRGACHVDN-HCZOVWHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-allyl-2'-deoxy-[5']uridylic acid; diammonium salt 在 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 生成 α-(Ξ)-oxiranyl-[5']thymidylic acid
  参考文献：
  名称：

  Synthetic inhibitors of Escherichia coli, calf thymus, and Ehrlich ascites tumor thymidylate synthetase

  摘要：

  In a study of active site binding the inhibition of thymidylate synthetase derived from Escherichia coli, calf thymus, and Ehrlich ascites tumor was examined using eight inhibitors. 5-Substituted 2'-deoxyuridine 5'-phosphate analogues used in this study are the hydroxymethyl, methoxymethyl, benzyloxymethyl, formyl, acetyl, allyl, and two potential active site alkylating substituents: 2,3-oxypropyl and the azidomethyl analogues. All compounds were competitive with the substrate, 2'-deoxyuridine 5'-phosphate; the most potent inhibitor was 5-formyl-dUMP (Ki = 0.1, 0.09, and 0.08 muM for the respective enzyme). The 5-hydroxymethyl, 5-benzyloxymethyl, and 5-azidomethyl derivatives of dUMP showed some differential inhibition; these compounds were two to three times more active against the ascites tumor enzyme than against the thymus enzyme.

  DOI：

  10.1021/jm00229a009