3-(4-Iodobutyl)-6-(3-ethyl-4-methylanilino)uracil | 308833-37-6

• 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: 3-(4-Iodobutyl)-6-(3-ethyl-4-methylanilino)uracil
• 英文别名: 6-(3-ethyl-4-methylanilino)-3-(4-iodobutyl)-1H-pyrimidine-2,4-dione
• CAS: 308833-37-6
• 化学式: C₁₇H₂₂IN₃O₂
• 分子量: 427.285
• InChiKey: BUYPPNJUNDITNW-UHFFFAOYSA-N

物化性质

• 熔点：
  201-203 °C(Solv: methanol (67-56-1))
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-Iodobutyl)-6-(3-ethyl-4-methylanilino)uracil 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以92%的产率得到3-(4-Azido-butyl)-6-(3-ethyl-4-methyl-phenylamino)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of Substituted 6-Anilinouracils and Their Inhibition of DNA Polymerase IIIC and Gram-Positive Bacterial Growth

  摘要：

  Certain substituted 6-anilinouracils are potent and selective inhibitors of Gram+ bacterial DNA polymerase IIIC (pol IIIC). In addition, analogues with 3-substituents in the uracil ring have potent antibacterial activity against Gram+ organisms in culture. In an attempt to find optimal anilino substituents for pol IIIC binding and optimal 3-substituents for antibacterial activity, we have prepared several series of 3-substituted-6-aminouracils and assayed their activity against pol IIIC from Bacillus subtilis and a panel of Gram+ and Gram- bacteria in culture. The 6-(3-ethyl-4-methylanilino) group and closely related substituent patterns maximized pol IIIC inhibition potency. Among a series of 3-(substituted-butyl)-6-(3-ethyl-4-methylanilino)uracils, basic amino substituents increased pol IIIC inhibition, but decreased antibacterial activity. The most potent antibacterials were simple hydroxybutyl and methoxybutyl derivatives, and hydrophobically substituted piperidinylbutyl derivatives.

  DOI：

  10.1021/jm020591z
• 作为产物：
  描述：

  6-chloro-3-(4-methoxybutyl)uracil 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 3-(4-Iodobutyl)-6-(3-ethyl-4-methylanilino)uracil
  参考文献：
  名称：

  Synthesis of Substituted 6-Anilinouracils and Their Inhibition of DNA Polymerase IIIC and Gram-Positive Bacterial Growth

  摘要：

  Certain substituted 6-anilinouracils are potent and selective inhibitors of Gram+ bacterial DNA polymerase IIIC (pol IIIC). In addition, analogues with 3-substituents in the uracil ring have potent antibacterial activity against Gram+ organisms in culture. In an attempt to find optimal anilino substituents for pol IIIC binding and optimal 3-substituents for antibacterial activity, we have prepared several series of 3-substituted-6-aminouracils and assayed their activity against pol IIIC from Bacillus subtilis and a panel of Gram+ and Gram- bacteria in culture. The 6-(3-ethyl-4-methylanilino) group and closely related substituent patterns maximized pol IIIC inhibition potency. Among a series of 3-(substituted-butyl)-6-(3-ethyl-4-methylanilino)uracils, basic amino substituents increased pol IIIC inhibition, but decreased antibacterial activity. The most potent antibacterials were simple hydroxybutyl and methoxybutyl derivatives, and hydrophobically substituted piperidinylbutyl derivatives.

  DOI：

  10.1021/jm020591z

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。
• N3-substituted 6-anilinopyrimidines and methods to treat-Gram-positive bacterial and mycoplasmal infections
  申请人：——

  公开号：US20030114445A1

  公开（公告）日：2003-06-19

  Compounds useful for treating Gram-positive bacterial and mycoplasmal infections are disclosed. The compounds have the general formulae shown below. 1

  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
• [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。
• Heterocyclic antibacterial compounds
  申请人：Microbiotix, Inc.

  公开号：US06777420B2

  公开（公告）日：2004-08-17

  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.

  本发明提供了一种抑制细菌DNA聚合酶IIIC和类型II细菌拓扑异构酶的杂环有机化合物。本发明还提供了在合成这种杂环有机化合物时有用的中间体化合物。本发明还描述了这种杂环有机分子的合成和用途。