2-Formyl-1-methylimidazole-4-carbonitrile | 1397696-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Formyl-1-methylimidazole-4-carbonitrile
• 英文别名: 2-formyl-1-methylimidazole-4-carbonitrile
• CAS: 1397696-92-2
• 化学式: C₆H₅N₃O
• 分子量: 135.125
• InChiKey: JUMSQMILKWHPDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Chloroquinoline-4-carbaldehyde[3-(cyclopropylmethyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]hydrazone 、 2-Formyl-1-methylimidazole-4-carbonitrile 在 哌啶 作用下， 生成 2-[2-[(6-Chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-5-methyl-4,6-dioxopyrazolo[3,4-d]pyrimidin-3-yl]-1-methylimidazole-4-carbonitrile
  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：

  4,5-Dibromo-2-(diethoxymethyl)-1-methylimidazole 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 作用下， 生成 2-Formyl-1-methylimidazole-4-carbonitrile
  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

文献信息

• POLYMERS FUNCTIONALIZED WITH PROTECTED OXIME COMPOUNDS CONTAINING A CYANO GROUP
  申请人：Bridgestone Corporation

  公开号：EP3143055A2

  公开（公告）日：2017-03-22
• [EN] POLYMERS FUNCTIONALIZED WITH PROTECTED OXIME COMPOUNDS CONTAINING A CYANO GROUP<br/>[FR] POLYMÈRES FONCTIONNALISÉS AVEC DES COMPOSÉS D'OXIME PROTÉGÉS CONTENANT UN GROUPE CYANO
  申请人：BRIDGESTONE CORP

  公开号：WO2015175280A2

  公开（公告）日：2015-11-19

  A method for preparing a functionalized polymer, the method comprising the steps of: (i) polymerizing monomer to form a reactive polymer, and (ii) reacting the reactive polymer with a protected oxime compound containing a cyano group.
• Design of inhibitors of Helicobacter pylori glutamate racemase as selective antibacterial agents: Incorporation of imidazoles onto a core pyrazolopyrimidinedione scaffold to improve bioavailabilty
  作者：Gregory S. Basarab、Pamela Hill、Charles J. Eyermann、Madhu Gowravaram、Helena Käck、Ekundayo Osimoni

  DOI：10.1016/j.bmcl.2012.07.004

  日期：2012.9

  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.