N-(3,4-dichlorobenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide | 1282522-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: N-(3,4-dichlorobenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide
• 英文别名: N-[(3,4-dichlorophenyl)methyl]-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide
• CAS: 1282522-70-6
• 化学式: C₁₇H₁₅Cl₂N₃O
• 分子量: 348.232
• InChiKey: WNTNMSZWLJSNPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,7-二甲基咪唑并[1,2-a]吡啶-3-羧酸乙酯 在 4-二甲氨基吡啶 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 48.0h， 生成 N-(3,4-dichlorobenzyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide
  参考文献：
  名称：

  Advent of Imidazo[1,2-a]pyridine-3-carboxamides with Potent Multi- and Extended Drug Resistant Antituberculosis Activity

  摘要：

  A set of nine 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamides and one 2,6-dimethylimidazo[1,2-a]pyrimidine-3-carboxamide were synthesized. The compounds were evaluated for their in vitro antituberculosis activity versus replicating, nonreplicating, multi- and extensive drug resistant Mtb strains. The MIC90 values of seven of these agents were <= mu M against the various tuberculosis strains tested. A representative compound of this class (1) was screened against seven nontubercular strains as well as other nonmycobacteria organisms and demonstrated remarkable microbe selectivity. A transcriptional profiling experiment of Mtb treated with compound 1 was performed to give a preliminary indication of the mode of action. Lastly, the in vivo ADME properties of compounds 1, 3, 4, and 6 were assessed. The 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamides are a druglike and synthetically accessible class of anti-TB agents that have excellent selective potency against multi- and extensive drug resistant TB and encouraging pharmacokinetics.

  DOI：

  10.1021/ml200036r

文献信息

• IMIDAZO[1,2-A]PYRIDINE COMPOUNDS, SYNTHESIS THEREOF, AND METHODS OF USING SAME
  申请人：University of Notre Dame du Lac

  公开号：EP3257854A1

  公开（公告）日：2017-12-20

  Embodiments relate to the field of chemistry and biochemistry, and, more specifically, to imidazopyridine compounds, synthesis thereof, and methods of using same. Disclosed herein are various imidazo[1,2-a]pyridine compounds and methods of using the novel compounds to treat or prevent tuberculosis in a subject or to inhibit fungal growth on plant species. Other embodiments include methods of synthesizing imidazo[1,2-a]pyridine compounds, such as the disclosed imidazo[1,2-a]pyridine compounds.

  本发明实施例涉及化学和生物化学领域，更具体地说，涉及咪唑并吡啶化合物、其合成及其使用方法。本发明公开了各种咪唑并[1,2-a]吡啶化合物以及使用这些新型化合物治疗或预防受试者的结核病或抑制植物真菌生长的方法。其他实施方案包括合成咪唑并[1,2-a]吡啶化合物的方法，例如所公开的咪唑并[1,2-a]吡啶化合物。
• Advent of Imidazo[1,2-<i>a</i>]pyridine-3-carboxamides with Potent Multi- and Extended Drug Resistant Antituberculosis Activity
  作者：Garrett C. Moraski、Lowell D. Markley、Philip A. Hipskind、Helena Boshoff、Sanghyun Cho、Scott G. Franzblau、Marvin J. Miller

  DOI：10.1021/ml200036r

  日期：2011.6.9

  A set of nine 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamides and one 2,6-dimethylimidazo[1,2-a]pyrimidine-3-carboxamide were synthesized. The compounds were evaluated for their in vitro antituberculosis activity versus replicating, nonreplicating, multi- and extensive drug resistant Mtb strains. The MIC90 values of seven of these agents were <= mu M against the various tuberculosis strains tested. A representative compound of this class (1) was screened against seven nontubercular strains as well as other nonmycobacteria organisms and demonstrated remarkable microbe selectivity. A transcriptional profiling experiment of Mtb treated with compound 1 was performed to give a preliminary indication of the mode of action. Lastly, the in vivo ADME properties of compounds 1, 3, 4, and 6 were assessed. The 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamides are a druglike and synthetically accessible class of anti-TB agents that have excellent selective potency against multi- and extensive drug resistant TB and encouraging pharmacokinetics.