6-amino-2-methoxy-3-(4-oxopentyl)-4-pyrimidone | 496943-47-6

• 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: 6-amino-2-methoxy-3-(4-oxopentyl)-4-pyrimidone
• 英文别名: 6-amino-2-methoxy-3-(4-oxopentyl)pyrimidin-4-one
• CAS: 496943-47-6
• 化学式: C₁₀H₁₅N₃O₃
• 分子量: 225.247
• InChiKey: KXZMNHYFANHQJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-amino-2-methoxy-3-(4-oxopentyl)-4-pyrimidone 、 3-ethyl-4-methylaniline hydrochloride 在 3-乙基-4-甲基苯胺 作用下， 反应 3.0h， 以Workup gave 92 mg (21% yield) of 3-(4-oxopentyl)-6-(3-ethyl-4-methylanilino)uracil的产率得到3-(4-oxopentyl)-6-(3-ethyl-4-methylanilino)uracil
  参考文献：
  名称：

  N3-substituted 6-anilinopyrimidines and methods to treat-Gram-positive bacterial and mycoplasmal infections

  摘要：

  公开了用于治疗革兰氏阳性细菌和支原体感染的化合物。这些化合物的一般式如下所示。1

  公开号：

  US20030114445A1
• 作为产物：
  描述：

  6-氨基-2-甲氧基-4-嘧啶酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 6-amino-2-methoxy-3-(4-oxopentyl)-4-pyrimidone 、 5-(6-Amino-2-methoxy-pyrimidin-4-yloxy)-pentan-2-one
  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

文献信息

• [EN] N3-SUBSTITUTED 6-ANILINOPYRIMIDINES AND METHODS TO TREAT GRAM-POSITIVE BACTERIAL AND MYCOPLASMAL INFECTIONS<br/>[FR] 6-ANILINOPYRIMIDINES N3-SUBSTITUEES ET METHODES DE TRAITEMENT D'INFECTIONS GRAM-POSITIF BACTERIENNES ET MYCOPLASMIQUES
  申请人：UNIV MASSACHUSETTS

  公开号：WO2003011297A1

  公开（公告）日：2003-02-13

  Compounds useful for treating Gram-positive bacterial and mycoplasmal infections are disclosed. The compounds have the general formulae (I) and (II).