6-(3-benzyloxy-2-(benzyloxymethyl)propyl)pyrimidin-2,4-dione | 1613134-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3-benzyloxy-2-(benzyloxymethyl)propyl)pyrimidin-2,4-dione
• 英文别名: 6-[3-phenylmethoxy-2-(phenylmethoxymethyl)propyl]-1H-pyrimidine-2,4-dione
• CAS: 1613134-58-9
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: AMWCTWOBLLKCMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(3-benzyloxy-2-(benzyloxymethyl)propyl)pyrimidin-2,4-dione 在 三氯化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 6-(3-hydroxy-2-(hydroxymethyl)propyl)-1-(methoxymethyl)pyrimidin-2,4-dione
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative evaluation of novel N-alkylated 6-isobutyl- and propyl pyrimidine derivatives

  摘要：

  A series of novel N-alkylated C-6-isobutyl- or -propyl pyrimidine derivatives were synthesized and their antiproliferative effect was evaluated on a panel of tumor cell lines including leukemia cell line K562 and normal diploid human fibroblasts. N-methoxymethylated 5-methylpyrimidin-2,4-dione with di (benzyloxy)isobutyl at C-6 (14b) showed the strongest effect on the cell growth at micromolar concentrations. Mechanisms of action for the lipophilic compound 14b predicted in silico, pointed to its anticancer and antimetastatic potential exerted through inhibition of DNA or RNA polymerases and adhesion molecules. The latter mechanism has been supported in vitro for adherent tumor cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.079
• 作为产物：
  描述：

  1,3-二苄氧基丙酮 在 4-二甲氨基吡啶 、 三甲基氯硅烷 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 甲苯 、 乙腈 为溶剂， 反应 64.0h， 生成 6-(3-benzyloxy-2-(benzyloxymethyl)propyl)pyrimidin-2,4-dione
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative evaluation of novel N-alkylated 6-isobutyl- and propyl pyrimidine derivatives

  摘要：

  A series of novel N-alkylated C-6-isobutyl- or -propyl pyrimidine derivatives were synthesized and their antiproliferative effect was evaluated on a panel of tumor cell lines including leukemia cell line K562 and normal diploid human fibroblasts. N-methoxymethylated 5-methylpyrimidin-2,4-dione with di (benzyloxy)isobutyl at C-6 (14b) showed the strongest effect on the cell growth at micromolar concentrations. Mechanisms of action for the lipophilic compound 14b predicted in silico, pointed to its anticancer and antimetastatic potential exerted through inhibition of DNA or RNA polymerases and adhesion molecules. The latter mechanism has been supported in vitro for adherent tumor cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.079

文献信息

• Synthesis and in vitro antiproliferative evaluation of novel N-alkylated 6-isobutyl- and propyl pyrimidine derivatives
  作者：Tatjana Gazivoda Kraljević、Nataša Ilić、Višnja Stepanić、Lana Sappe、Jasna Petranović、Sandra Kraljević Pavelić、Silvana Raić-Malić

  DOI：10.1016/j.bmcl.2014.04.079

  日期：2014.7

  A series of novel N-alkylated C-6-isobutyl- or -propyl pyrimidine derivatives were synthesized and their antiproliferative effect was evaluated on a panel of tumor cell lines including leukemia cell line K562 and normal diploid human fibroblasts. N-methoxymethylated 5-methylpyrimidin-2,4-dione with di (benzyloxy)isobutyl at C-6 (14b) showed the strongest effect on the cell growth at micromolar concentrations. Mechanisms of action for the lipophilic compound 14b predicted in silico, pointed to its anticancer and antimetastatic potential exerted through inhibition of DNA or RNA polymerases and adhesion molecules. The latter mechanism has been supported in vitro for adherent tumor cell lines. (C) 2014 Elsevier Ltd. All rights reserved.