Acetic acid 5-[4-(3-ethyl-4-methyl-phenylamino)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-pentyl ester | 870451-83-5

• 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: Acetic acid 5-[4-(3-ethyl-4-methyl-phenylamino)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-pentyl ester
• 英文别名: 5-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1H-pyrimidin-3-yl]pentyl acetate
• CAS: 870451-83-5
• 化学式: C₂₀H₂₇N₃O₄
• 分子量: 373.452
• InChiKey: ZKLVXXLJQMIBHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid 5-[4-(3-ethyl-4-methyl-phenylamino)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-pentyl ester 在 ammonium hydroxide 、 碘代三甲硅烷 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 79.0h， 生成 3-(5-iodopentyl)-6-(3-ethyl-4-methylanilino)uracil
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of 3-Substituted-6-(3-ethyl-4-methylanilino)uracils

  摘要：

  Numerous 3-substituted-6-(3-ethyl-4-methylanilino)uracils (EMAU) have been synthesized and screened for their capacity to inhibit the replication-specific bacterial DNA polymerase IIIC (pol IIIC) and the growth of Gram+ bacteria in culture. Direct alkylation of 2-methoxy-6-amino-4-pyrimidone produced the N3-substituted derivatives, which were separated from the byproduct 4-alkoxy analogues. The N3-substituted derivatives were heated with a mixture of 3-ethyl-4-methylaniline and its hydrochloride to effect displacement of the 6-amino group and simultaneous demethylation of the 2-methoxy group to yield target compounds in good yields. Certain intermediates, e.g. the 3-(iodoalkyl) compounds, were converted to a variety of (3-substituted-alkyl)-EMAUs by displacement. Most compounds were potent competitive inhibitors of pol IIIC (K(i)s 0.02-0.5 mu M), and those with neutral, moderately polar 3-substituents had potent antibacterial activity against Gram+ organisms in culture (MICs 0.125-10 mu g/mL). Several compounds protected mice from lethal intraperitoneal (ip) infections with S. aureus (Smith) when given by the ip route. A water soluble derivative, 3-(4-morpholinylbutyl)-EMAU hydrochloride, given subcutaneously, prolonged the life of infected mice in a dose dependent manner.

  DOI：

  10.1021/jm050517r
• 作为产物：
  描述：

  Acetic acid 5-(4-amino-2-methoxy-6-oxo-6H-pyrimidin-1-yl)-pentyl ester 、 3-ethyl-4-methylaniline hydrochloride 在 3-乙基-4-甲基苯胺 作用下， 以81%的产率得到Acetic acid 5-[4-(3-ethyl-4-methyl-phenylamino)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-pentyl ester
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of 3-Substituted-6-(3-ethyl-4-methylanilino)uracils

  摘要：

  Numerous 3-substituted-6-(3-ethyl-4-methylanilino)uracils (EMAU) have been synthesized and screened for their capacity to inhibit the replication-specific bacterial DNA polymerase IIIC (pol IIIC) and the growth of Gram+ bacteria in culture. Direct alkylation of 2-methoxy-6-amino-4-pyrimidone produced the N3-substituted derivatives, which were separated from the byproduct 4-alkoxy analogues. The N3-substituted derivatives were heated with a mixture of 3-ethyl-4-methylaniline and its hydrochloride to effect displacement of the 6-amino group and simultaneous demethylation of the 2-methoxy group to yield target compounds in good yields. Certain intermediates, e.g. the 3-(iodoalkyl) compounds, were converted to a variety of (3-substituted-alkyl)-EMAUs by displacement. Most compounds were potent competitive inhibitors of pol IIIC (K(i)s 0.02-0.5 mu M), and those with neutral, moderately polar 3-substituents had potent antibacterial activity against Gram+ organisms in culture (MICs 0.125-10 mu g/mL). Several compounds protected mice from lethal intraperitoneal (ip) infections with S. aureus (Smith) when given by the ip route. A water soluble derivative, 3-(4-morpholinylbutyl)-EMAU hydrochloride, given subcutaneously, prolonged the life of infected mice in a dose dependent manner.

  DOI：

  10.1021/jm050517r