3-(3,4-dihydro-5-(2-methyl-4-nitroimidazol-1-yl)-2,4-dioxopyrimidin-1(2H)-yl)propanoic acid | 1174386-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3,4-dihydro-5-(2-methyl-4-nitroimidazol-1-yl)-2,4-dioxopyrimidin-1(2H)-yl)propanoic acid
• CAS: 1174386-64-1
• 化学式: C₁₁H₁₁N₅O₆
• 分子量: 309.238
• InChiKey: MYGBLIHUJAZTDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.59
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  153.12
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(3-amino-propyl)-5-methyl-1H-pyrimidine-2,4-dione trifluoroacetate 、 3-(3,4-dihydro-5-(2-methyl-4-nitroimidazol-1-yl)-2,4-dioxopyrimidin-1(2H)-yl)propanoic acid 在 N-甲基吗啉 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到3-(3,4-dihydro-5-(2-methyl-4-nitroimidazol-1-yl)-2,4-dioxopyrimidin-1(2H)-yl)-N-(3-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)propyl)propanamide
  参考文献：
  名称：

  Novel Acyclic Amide-Conjugated Nucleosides and Their Analogues

  摘要：

  An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2'-cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5'-amino-5'-deoxythymidine and 5-aminouracil.

  DOI：

  10.1080/15257770902736467
• 作为产物：
  描述：

  3-(3,4-dihydro-5-(2-methyl-4-nitroimidazol-1-yl)-2,4-dioxopyrimidin-1(2H)-yl)propanoic acid methyl ester 在 盐酸 、 水 作用下， 以65%的产率得到3-(3,4-dihydro-5-(2-methyl-4-nitroimidazol-1-yl)-2,4-dioxopyrimidin-1(2H)-yl)propanoic acid
  参考文献：
  名称：

  Novel Acyclic Amide-Conjugated Nucleosides and Their Analogues

  摘要：

  An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2'-cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5'-amino-5'-deoxythymidine and 5-aminouracil.

  DOI：

  10.1080/15257770902736467