1-<(2-acetoxyethoxy)methyl>-5-(m-benzyloxy)benzylbarbituric acid | 152099-80-4

• 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: 1-<(2-acetoxyethoxy)methyl>-5-(m-benzyloxy)benzylbarbituric acid
• 英文别名: 1-[(2-acetoxyethoxy)methyl]-5-(m-benzyloxy)benzylbarbituric acid；2-[[2,4,6-Trioxo-5-[(3-phenylmethoxyphenyl)methyl]-1,3-diazinan-1-yl]methoxy]ethyl acetate
• CAS: 152099-80-4
• 化学式: C₂₃H₂₄N₂O₇
• 分子量: 440.453
• InChiKey: LCCLZYUDQPJXCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-<(2-acetoxyethoxy)methyl>-5-(m-benzyloxy)benzylbarbituric acid 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以71%的产率得到1-(2-羟基乙氧基甲基)-3-[[3-(苯基甲氧基)苯基]甲基]-1,3-二嗪农-2,4,6-三酮
  参考文献：
  名称：

  Exploring new inhibitors of Plasmodium falciparum purine nucleoside phosphorylase

  摘要：

  Plasmodium falciparum purine nucleoside phosphorylase (PfPNP) has a central role in purine salvage and inhibitors of the enzyme have been shown to have antiplasmodial activity. The enzyme preferentially uses inosine as substrate (K-m = 51 mu M, k(cat)/K-m = 7.4 x 10(4) M-1 s(-1)), but can also use uridine, albeit less efficiently (K-m = 85 mu M, k(cat)/K-m = 306 M-1 s(-1)). In an effort to identify new PfPNP inhibitors, two series of compounds were prepared. Series 1 was based on known human uridine phosphorylase inhibitors whilst series 2 was uracil equivalents of purine-based PNP transition state inhibitors. These two series of compounds were assayed for inhibition of both PfPNP activity and growth of P. falciparum. The transition state analogues were found to be moderate inhibitors of PfPNP (most potent compound, K-i = 6 mu M). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.026
• 作为产物：
  描述：

  1-<(2-acetoxyethoxy)methyl>barbituric acid 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 1-<(2-acetoxyethoxy)methyl>-5-(m-benzyloxy)benzylbarbituric acid
  参考文献：
  名称：

  Tzeng, Cherng-Chyi; Panzica, Raymond P.; Naguib, Fardos N.M., Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1399 - 1404

  摘要：

  DOI：