6-Chloro-1-(cyclopropylmethyl)-3-methylpyrimidine-2,4(1H,3H)-dione | 491615-29-3

• 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-Chloro-1-(cyclopropylmethyl)-3-methylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 6-chloro-1-(cyclopropylmethyl)-3-methylpyrimidine-2,4-dione
• CAS: 491615-29-3
• 化学式: C₉H₁₁ClN₂O₂
• 分子量: 214.652
• InChiKey: NCAXDUANVVANMP-UHFFFAOYSA-N

物化性质

• 沸点：
  290.0±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Chloro-1-(cyclopropylmethyl)-3-methylpyrimidine-2,4(1H,3H)-dione 在 肼 作用下， 反应 16.0h， 生成 6-Chloroquinoline-4-carbaldehyde[3-(cyclopropylmethyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]hydrazone
  参考文献：
  名称：

  Design of inhibitors of Helicobacter pylori glutamate racemase as selective antibacterial agents: Incorporation of imidazoles onto a core pyrazolopyrimidinedione scaffold to improve bioavailabilty

  摘要：

  Structure-activity relationships are presented around a series of pyrazolopyrimidinediones that inhibit the growth of Helicobacter pylori by targeting glutamate racemase, an enzyme that provides d-glutamate for the construction of N-acetylglucosamine-N-acetylmuramic acid peptidoglycan subunits assimilated into the bacterial cell wall. Substituents on the inhibitor scaffold were varied to optimize target potency, antibacterial activity and in vivo pharmacokinetic stability. By incorporating an imidazole ring at the 7-position of scaffold, high target potency was achieved due to a hydrogen bonding network that occurs between the 3-position nitrogen atom, a bridging water molecule and the side chains Ser152 and Trp244 of the enzyme. The lipophilicity of the scaffold series proved important for expression of antibacterial activity. Clearances in vitro and in vivo were monitored to identify compounds with improved plasma stability. The basicity of the imidazole may contribute to increased aqueous solubility at lower pH allowing for improved oral bioavailability.

  DOI：

  10.1016/j.bmcl.2012.07.004
• 作为产物：
  描述：

  6-氯-3-甲基尿嘧啶 、 溴甲基环丙烷 生成 6-Chloro-1-(cyclopropylmethyl)-3-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Chemical compounds

  摘要：

  本发明涉及一种公式（1）的化合物（此处应插入一个化学式-请参阅附带的文本副本），其中Q为-CO-或-C（R4）（R5）-（其中R4为氢原子或C1-4烷基，R5为氢原子或羟基），Ar为一个5-至10-成员的芳香环系统，其中最多4个环原子可以是氮、氧和硫的杂原子，该环系统可选地由规定中定义的一个或多个取代基取代。本发明还涉及制备、含有该公式（1）的化合物的制药组合物以及使用该化合物的方法，特别是在自身免疫性疾病的调节中的使用方法。

  公开号：

  US07361660B2

文献信息

• Chemical Compounds
  申请人：Reynolds Rachel Heulwen

  公开号：US20080153855A1

  公开（公告）日：2008-06-26

  The invention relates to a compound of formula (1) in which Q is —CO— or —C(R 4 )(R 5 )—, where R 4 is a hydrogen atom or C 1-4 alkyl and R 5 is a hydrogen atom or hydroxy group; and Ar is a 5- to 10-membered aromatic ring system where up to 4 ring atoms may be heteroatoms independently selected from nitrogen, oxygen and sulphur, the ring system being optionally substituted by one or more substituents as defined in the specification. It also relates to methods of preparing, pharmaceutical compositions containing and methods of using the compound of the formula (1), particularly in the modulation of autoimmune disease.

  本发明涉及一种化合物，其化学式为（1），其中Q为—CO—或—C（R4）（R5）—，其中R4为氢原子或C1-4烷基，R5为氢原子或羟基；Ar为一个5-到10-成员的芳香环系，其中最多4个环原子可以是氮、氧和硫的杂原子，该环系可以被定义在规范中的一个或多个取代基所取代。本发明还涉及制备方法、含有该化合物的药物组合物以及使用该化合物的方法，特别是在自身免疫性疾病的调节方面。
• US7361660B2
  申请人：——

  公开号：US7361660B2

  公开（公告）日：2008-04-22