5-methyl-1-(piperidin-3-yl)-pyrimidine-2,4(1H,3H)-dione | 1146781-28-3

• 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: 5-methyl-1-(piperidin-3-yl)-pyrimidine-2,4(1H,3H)-dione
• 英文别名: (RS)-3-(thymin-1-yl)piperidine；m-Piperidinyl thymine；5-methyl-1-piperidin-3-ylpyrimidine-2,4-dione
• CAS: 1146781-28-3
• 化学式: C₁₀H₁₅N₃O₂
• 分子量: 209.248
• InChiKey: BBLDMGQRHJEJKW-UHFFFAOYSA-N

物化性质

• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-1-(piperidin-3-yl)-pyrimidine-2,4(1H,3H)-dione 、 间苯氧基苯甲醛 在 (polystyrylmethyl)-trimethylammonium cyanoborohydride 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 5-methyl-1-(1-(3-phenoxybenzyl)piperidin-3-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Discovery of Selective and Potent Inhibitors of Gram-Positive Bacterial Thymidylate Kinase (TMK)

  摘要：

  Thymidylate kinase (TMK) is an essential enzyme in bacterial DNA synthesis. The deoxythymidine monophosphate (dTMP) substrate binding pocket was targeted in rational-design, structure-supported effort, yielding a unique series of antibacterial agents showing a novel, induced-fit binding mode. Lead optimization, aided by X-ray crystallography, led to picomolar inhibitors of both Streptococcus pneumoniae and Staphylococcus aureus TMK. MICs < 1 mu g/mL were achieved against methicillin-resistant S. aureus (MRSA), S. pneumoniae, and vancomycin-resistant. Enterococcus (VRE). Log D adjustments yielded single diastereomers 14 (TK-666) and 46, showing a broad antibacterial spectrum against Gram-positive bacteria and excellent selectivity against the human thymidylate kinase ortholog.

  DOI：

  10.1021/jm3011806
• 作为产物：
  描述：

  N-BOC-3-羟基哌啶 在 4-二甲氨基吡啶 、 sodium azide 、 10% palladium on activated charcoal 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 5-methyl-1-(piperidin-3-yl)-pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  The synthesis of piperidine nucleoside analogs—a comparison of several methods to access the introduction of nucleobases

  摘要：

  This work deals with the synthesis of piperidine and hydroxypiperidine analogs of nucleosides. Starting from commercially available 3-hydroxypiperidine, proline or 4-hydroxyproline, a series of piperidine derivatives of both purine and pyrimidine nucleobases was prepared. Various methods of nucleobase attachment were evaluated. The prepared compounds were tested for cytostatic, antibacterial, and antiviral properties but no significant activity was found. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.029