6-(2,3-二羟基丙基)-5-甲基-2,4(1H,3H)-嘧啶二酮 | 820966-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-(2,3-二羟基丙基)-5-甲基-2,4(1H,3H)-嘧啶二酮
• 英文名称: 6-(2,3-dihydroxypropyl)-5-methyl-(1H,3H)-pyrimidine-2,4-dione
• 英文别名: 6-(2,3-dihydroxypropyl)thymine；6-(2,3-Dihydroxypropyl)-5-methylpyrimidine-2,4(1H,3H)-dione；6-(2,3-dihydroxypropyl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 820966-05-0
• 化学式: C₈H₁₂N₂O₄
• 分子量: 200.194
• InChiKey: LSDREOWZERBZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2,3-二羟基丙基)-5-甲基-2,4(1H,3H)-嘧啶二酮 在 4-二甲氨基吡啶 、 二甲氨基三氟化硫 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 6-fluoro-4-methylpyrrolido[1,2-c]pyrimidine-1,3-dione
  参考文献：
  名称：

  Synthesis of the Novel Bicyclic Oxepinopyrimidine and Fluorinated Pyrrolidinopyrimidines

  摘要：

  DOI：

  10.3987/com-04-10176
• 作为产物：
  描述：

  2,4-二甲氧基-5,6-二甲基嘧啶 在 正丁基锂 、 水 、 三氯化硼 、 碳酸氢钠 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 6-(2,3-二羟基丙基)-5-甲基-2,4(1H,3H)-嘧啶二酮
  参考文献：
  名称：

  Synthesis, ¹⁸F‐Radiolabelling and Biological Evaluations of C‐6 Alkylated Pyrimidine Nucleoside Analogues

  摘要：

  Synthesis of pyrimidine derivatives with a side-chain attached to the C-6 of pyrimidine ring (6-14) is reported. Target compounds 8 and 12 were subjected to in vitro phosphorylation tests, determination of their binding affinities to herpes simplex virus (HSV-1) thymidine kinase (TK) and catalytic turnover constants. Fluorinated pyrimidine derivative 12 (40 muM) exhibited better binding affinity for HSV-1 TK than acyclovir (ACV, 170 muM) and ganciclovir (GCV, 48 muM). Catalytic turnover constant (k(cat)) of 12 (0.08 s(-1)) was close to the k(cat) values of ACV (0.10 s(-1)) and GCV (0.10 s(-1)). Furthermore, compounds 8 and 12 showed no cytotoxic effects in HSV-1 TK-transduced and non-transduced cell lines. Besides, compounds 8 and 12 did not exhibit antiviral or cytostatic activities against several viruses and malignant tumor cell lines that were evaluated. The new fluorinated pyrimidine derivative 16 that is phosphorylated by HSV-1 TK could be developed as non-toxic PET-tracer molecule. Thus, F-18 labelling of the precursor 14 was performed by nucleophilic substitution using [F-18] tetrabutylammonium fluoride as the fluorinating reagent.

  DOI：

  10.1081/ncn-200033914