2-Diethoxymethyl-1-methyl-imidazol | 13750-82-8

• 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-Diethoxymethyl-1-methyl-imidazol
• 英文别名: Diethylacetyl von 1-Methyl-imidazol-2-carbaldehyd；2-diethoxymethyl-1-methyl-1H-imidazole；1H-Imidazole, 2-(diethoxymethyl)-1-methyl-；2-(diethoxymethyl)-1-methylimidazole
• CAS: 13750-82-8
• 化学式: C₉H₁₆N₂O₂
• 分子量: 184.238
• InChiKey: WPFFTKWYVIOSSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Diethoxymethyl-1-methyl-imidazol 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 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
• 作为产物：
  描述：

  原甲酸三乙酯 、 1-甲基-1H-咪唑-2-甲醛 在 对甲苯磺酸 作用下， 生成 2-Diethoxymethyl-1-methyl-imidazol
  参考文献：
  名称：

  幽门螺杆菌谷氨酸消旋酶抑制剂作为选择性抗菌剂的设计：增加暴露量的新型前药方法。

  摘要：

  高通量筛选发现，吡唑并嘧啶二酮是幽门螺杆菌谷氨酸消旋酶（MurI）的一种选择性，低微摩尔抑制剂。支架周围取代基的变化导致低纳摩尔抑制剂并提高了抗菌活性。该程序面临的挑战是将出色的酶抑制作用转化为适用于口服治疗的有效抗菌活性和药代动力学。针对小鼠的MurI抑制，针对幽门螺杆菌的活性，微粒体稳定性和药代动力学对化合物进行了分析。模拟合成和生物学测试的反复循环导致了具有针对低MIC（2 microg / ml）和良好的微粒体稳定性而优化的取代基的化合物。为了获得高生物利用度，

  DOI：

  10.1016/j.bmcl.2008.06.092

文献信息

• Substituted heterocyclylisoquinolinium salts and compositions and
  申请人：Sterling Winthrop Inc.

  公开号：US05604224A1

  公开（公告）日：1997-02-18

  Substitutued heterocyclylisoquinolinium salts, pharmaceutical compositions containing them and methods for the treatment or prevention of neurodegenerative disorders or neurotoxic injuries utilizing them.

  替代杂环异喹啉盐，含有它们的制药组合物以及利用它们治疗或预防神经退行性疾病或神经毒性损伤的方法。
• Substituted heterocyclylisoquinolinium salts and compositions and method
  申请人：Sterling Winthrop Inc.

  公开号：US05569655A1

  公开（公告）日：1996-10-29

  Substitutued heterocyclylisoquinolinium salts, pharmaceutical compositions containing them and methods for the treatment or prevention of neurodegenerative disorders or neurotoxic injuries utilizing them.

  替代杂环异喹啉盐，含有它们的药物组合物以及利用它们治疗或预防神经退行性疾病或神经毒性损伤的方法。
• BORAI, M. EL;MOUSTAFA, A. H.;ANWAR, M.;GHATTAS, A. G., CROAT. CHEM. ACTA, 1981, 54, N 2, 211-216
  作者：BORAI, M. EL、MOUSTAFA, A. H.、ANWAR, M.、GHATTAS, A. G.

  DOI：——

  日期：——
• ANTONI I.; CRISTALLI G.; FRANCHETTI P.; GRIFANTINI M.; GULINI U.; MARTELL+, J. HETEROCYCL. CHEM., 1978, 15, NO 7, 1201-1203
  作者：ANTONI I.、 CRISTALLI G.、 FRANCHETTI P.、 GRIFANTINI M.、 GULINI U.、 MARTELL+

  DOI：——

  日期：——