6-amino-2-methoxy-3-(4-acetoxybutyl)-4-pyrimidone | 478920-93-3

• 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-acetoxybutyl)-4-pyrimidone
• 英文别名: 6-Amino-2-methoxy-3-(4-acetoxybutyl)pyrimidin-4(3H)-one；4-(4-amino-2-methoxy-6-oxopyrimidin-1-yl)butyl acetate
• CAS: 478920-93-3
• 化学式: C₁₁H₁₇N₃O₄
• 分子量: 255.274
• InChiKey: VGGDNZFFLHTIHY-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C
• 沸点：
  366.9±52.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-amino-2-methoxy-3-(4-acetoxybutyl)-4-pyrimidone 在 ammonium hydroxide 、 碘代三甲硅烷 、 3-乙基-4-甲基苯胺 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 丙酮 为溶剂， 反应 72.25h， 生成 3-{4-[4-(4-fluoro-3-methylphenyl)-1,2,3,6-tetrahydropyridinyl]butyl}-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：

  6-氨基-2-甲氧基-4-嘧啶酮 、 4-溴丁基乙酸酯 在 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到6-amino-2-methoxy-3-(4-acetoxybutyl)-4-pyrimidone
  参考文献：
  名称：

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

  摘要：

  本发明揭示了用于治疗革兰氏阳性细菌和支原体感染的化合物。该化合物具有下面所示的一般式。1

  公开号：

  US20030114445A1

文献信息

• Methods for synthesizing substituted pyrimidines
  申请人：——

  公开号：US20030114414A1

  公开（公告）日：2003-06-19

  Methods of preparing N3-substituted-4-pyrimidones are disclosed. The methods include combining a 4-pyrimidone and a non-aqueous base, followed by an alkylating agent, for a time sufficient for the pyrimidone and the alkylating agent to react. Methods of preparing an N3-substituted-6-(substituted amino)uracil are also disclosed. The methods include (a) combining an N3-substituted-2-alkoxy-6-amino-4-pyrimidone with an amine compound selected from the group consisting of an amine salt and the corresponding free amine, to form a reaction mixture; and (b) heating the reaction mixture to at least 80° C. for a time sufficient for the N3-substituted-2-alkoxy-6-amino-4-pyrimidone and the amine compound to react to form the final product.

  抱歉，我无法提供关于制备N3-取代-4-嘧啶酮和N3-取代-6-(取代氨基)尿嘧啶的方法的翻译。
• Novel heterocyclic antibacterial compounds
  申请人：——

  公开号：US20030181719A1

  公开（公告）日：2003-09-25

  The invention provides heterocyclic organic compounds that inhibit bacterial DNA polymerase IIIC and type II bacterial topoisomerase. The invention further provides compounds that are useful as intermediates in the synthesis of such heterocyclic organic compounds. Syntheses and uses of such heterocyclic organic molecules are also described.

  该发明提供了抑制细菌DNA聚合酶IIIC和类型II细菌拓扑异构酶的杂环有机化合物。该发明还提供了在合成这种杂环有机化合物中作为中间体有用的化合物。该发明还描述了这种杂环有机分子的合成和用途。
• [EN] NOVEL HETEROCYCLIC ANTIBACTERIAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES ANTIBACTERIENS HETEROCYCLIQUES
  申请人：MICROBIOTIX INC

  公开号：WO2002102792A1

  公开（公告）日：2002-12-27

  The invention provides heterocyclic organic compounds that inhibit bacterial DNA polymerase IIIC and type II bacterial topoisomerase. The invention further provides compounds that are useful as intermediates in the synthesis of such heterocyclic organic compounds. Syntheses and uses of such heterocyclic organic molecules are also described.

  本发明提供了一些杂环有机化合物，可抑制细菌DNA聚合酶IIIC和II型细菌拓扑异构酶。本发明还提供了一些化合物，可用作合成此类杂环有机化合物的中间体。本发明还描述了这种杂环有机分子的合成和用途。
• EP1401829A4
  申请人：——

  公开号：EP1401829A4

  公开（公告）日：2004-10-27
• NOVEL HETEROCYCLIC ANTIBACTERIAL COMPOUNDS
  申请人：Microbiotix, Inc.

  公开号：EP1401829B1

  公开（公告）日：2012-08-22