5-nitro-1,3-bis-n-propyluracil | 1174656-94-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-nitro-1,3-bis-n-propyluracil
• 英文别名: 5-Nitro-1,3-dipropylpyrimidine-2,4-dione
• CAS: 1174656-94-0
• 化学式: C₁₀H₁₅N₃O₄
• 分子量: 241.247
• InChiKey: DAAJRPJTFCFXFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/38
• WGK Germany：
  3
• 危险类别：
  Xi

反应信息

• 作为反应物：
  描述：

  5-nitro-1,3-bis-n-propyluracil 在 铁粉 、 溶剂黄146 作用下， 反应 4.0h， 以86%的产率得到5-amino-1,3-bis-n-propyluracil
  参考文献：
  名称：

  Synthesis of hybrid analogues of caffeine and eudistomin D and its affinity for adenosine receptors

  摘要：

  Four bis-N-n-propyl analogues (3-6) in the uracil ring of two hybrid molecules (1 and 2) of caffeine and eudistomin D, a beta-carboline alkaloid from a marine tunicate, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. All the compounds (3-6) showed better potency as adenosine receptor ligands than caffeine. Bis-N-n-propylation (3 and 4, respectively) of the uracil ring in 1 and 2 resulted in higher affinity for A(1) and A(2A) adenosine receptors. Furthermore, it was found that a compound (5) possessing a n-propyloxy group at C-7 in compound 3 with a nitrogen at the beta-position of the pyridine ring (beta-N type) enhanced remarkably affinity for adenosine receptor A3 subtype, while n-propyloxy substitution (compound 6) at C-5 in compound 4 with a nitrogen at the delta-position of the pyridine ring (delta-N type) reduced affinity for all the adenosine receptor, A(1), A(2A), and A(3). Among all the compounds (1-6) examined, compound 5 showed the most potent affinity for adenosine receptor A(3) subtype (K-i value, 0.00382 mu M). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.036
• 作为产物：
  描述：

  1,3-bis-n-propyluracil 在 硫酸 、 硝酸 作用下， 以98%的产率得到5-nitro-1,3-bis-n-propyluracil
  参考文献：
  名称：

  Synthesis of hybrid analogues of caffeine and eudistomin D and its affinity for adenosine receptors

  摘要：

  Four bis-N-n-propyl analogues (3-6) in the uracil ring of two hybrid molecules (1 and 2) of caffeine and eudistomin D, a beta-carboline alkaloid from a marine tunicate, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. All the compounds (3-6) showed better potency as adenosine receptor ligands than caffeine. Bis-N-n-propylation (3 and 4, respectively) of the uracil ring in 1 and 2 resulted in higher affinity for A(1) and A(2A) adenosine receptors. Furthermore, it was found that a compound (5) possessing a n-propyloxy group at C-7 in compound 3 with a nitrogen at the beta-position of the pyridine ring (beta-N type) enhanced remarkably affinity for adenosine receptor A3 subtype, while n-propyloxy substitution (compound 6) at C-5 in compound 4 with a nitrogen at the delta-position of the pyridine ring (delta-N type) reduced affinity for all the adenosine receptor, A(1), A(2A), and A(3). Among all the compounds (1-6) examined, compound 5 showed the most potent affinity for adenosine receptor A(3) subtype (K-i value, 0.00382 mu M). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.036