ethyl-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate | 371925-04-1

• 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: ethyl-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate
• 英文别名: 3-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylic acid ethyl ester；ethyl 3-(2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enoate
• CAS: 371925-04-1
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: CLTQMIJFRLDBCW-UHFFFAOYSA-N

物化性质

• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate 在 三氟甲磺酸三甲基硅酯 、 5%-palladium/activated carbon 氢气 、 六甲基二硅氮烷 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、399.99 kPa 条件下， 反应 2.0h， 生成 ethyl-3-<1-(2-deoxy-α-D-erythro-pentofuranosyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl>propionate
  参考文献：
  名称：

  Griengl; Hayden; Schwarz, European Journal of Medicinal Chemistry, 1985, vol. 20, # 2, p. 105 - 110

  摘要：

  DOI：
• 作为产物：
  描述：

  5-碘尿嘧啶 、 丙烯酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 生成 ethyl-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate
  参考文献：
  名称：

  Inhibition of Mycobacterial Replication by Pyrimidines Possessing Various C-5 Functionalities and Related 2′-Deoxynucleoside Analogues Using in Vitro and in Vivo Models

  摘要：

  Tuberculosis (TB) has become an increasing problem since the emergence of human immunodeficiency virus and increasing appearance of drug-resistant strains. There is an urgent need to advance our knowledge and discover a new class of agents that are distinct than current therapies. Antimycobacterial activities of several 5-alkyl, 5-alkynyl, furanopyrimiclines and related 2'-deoxynucleosides were investigated against Mycobacterium tuberculosis. Compounds with 5-arylalkynyl substituents (23-26,33, 35) displayed potent in vitro antitubercular activity against Mycobacterium bovis and Mycobacterium tuberculosis. The in vivo activity of 5-(2-pyridylethyny1)-uracil (26) and its 2'-deoxycytidine analogue, 5-(2-pyridylethynyI)-2'-deoxycytidine (35), was assessed in BA LB/c mice infected with M. tuberculosis (H 37 Ra). Both compounds 26 and 35 given at a dose of 50 mg/kg for 5 weeks showed promising in vivo efficacy in a mouse model, with the 2'-deoxycytidine derivative being more effective than the uracil analogue and a reference drug o-cycloserine. These data indicated that there is a significant potential in this class of compounds.

  DOI：

  10.1021/jm100568q

文献信息

• Inhibition of Mycobacterial Replication by Pyrimidines Possessing Various C-5 Functionalities and Related 2′-Deoxynucleoside Analogues Using in Vitro and in Vivo Models
  作者：Naveen C. Srivastav、Dinesh Rai、Christopher Tse、B. Agrawal、Dennis Y. Kunimoto、Rakesh Kumar

  DOI：10.1021/jm100568q

  日期：2010.8.26

  Tuberculosis (TB) has become an increasing problem since the emergence of human immunodeficiency virus and increasing appearance of drug-resistant strains. There is an urgent need to advance our knowledge and discover a new class of agents that are distinct than current therapies. Antimycobacterial activities of several 5-alkyl, 5-alkynyl, furanopyrimiclines and related 2'-deoxynucleosides were investigated against Mycobacterium tuberculosis. Compounds with 5-arylalkynyl substituents (23-26,33, 35) displayed potent in vitro antitubercular activity against Mycobacterium bovis and Mycobacterium tuberculosis. The in vivo activity of 5-(2-pyridylethyny1)-uracil (26) and its 2'-deoxycytidine analogue, 5-(2-pyridylethynyI)-2'-deoxycytidine (35), was assessed in BA LB/c mice infected with M. tuberculosis (H 37 Ra). Both compounds 26 and 35 given at a dose of 50 mg/kg for 5 weeks showed promising in vivo efficacy in a mouse model, with the 2'-deoxycytidine derivative being more effective than the uracil analogue and a reference drug o-cycloserine. These data indicated that there is a significant potential in this class of compounds.
• Griengl; Hayden; Schwarz, European Journal of Medicinal Chemistry, 1985, vol. 20, # 2, p. 105 - 110
  作者：Griengl、Hayden、Schwarz、et al.

  DOI：——

  日期：——