N-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)methyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide | 1300031-14-4

• 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-chloro-5-(trifluoromethyl)pyridin-2-yl)methyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide
• 英文别名: N-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methyl]-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide
• CAS: 1300031-14-4
• 化学式: C₁₇H₁₄ClF₃N₄O
• 分子量: 382.773
• InChiKey: METKHBKAYLOUKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  6

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 、 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 12.0h， 生成 N-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)methyl)-2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamide
  参考文献：
  名称：

  Advancement of Imidazo[1,2-a]pyridines with Improved Pharmacokinetics and nM Activity vs. Mycobacterium tuberculosis

  摘要：

  A set of 14 imidazo[1,2-a]pyridine-3-carboxamides was synthesized and screened against Mycobacterium tuberculosis H(37)Rv. The minimum inhibitory concentrations of 12 of these agents were <= 1 mu M against replicating bacteria and 5 compounds (9, 12, 16, 17, and 18) had MIC values <= 0.006 mu M. Compounds 13 and 18 were screened against a panel of MDR and XDR drug resistant clinical Mtb strains with the potency of 18 surpassing that of clinical candidate PA-824 by nearly 10-fold. The in vivo pharmacokinetics of compounds 13 and 18 were evaluated in male mice by oral (PO) and intravenous (IV) routes. These results indicate that readily synthesized imidazo[1,2-a]pyridine-3-carboxamides are an exciting new class of potent, selective anti-TB agents that merit additional development opportunities.

  DOI：

  10.1021/ml400088y

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。
• Advancement of Imidazo[1,2-<i>a</i>]pyridines with Improved Pharmacokinetics and nM Activity vs. <i>Mycobacterium tuberculosis</i>
  作者：Garrett C. Moraski、Lowell D. Markley、Jeffrey Cramer、Philip A. Hipskind、Helena Boshoff、Mai A. Bailey、Torey Alling、Juliane Ollinger、Tanya Parish、Marvin J. Miller

  DOI：10.1021/ml400088y

  日期：2013.7.11

  A set of 14 imidazo[1,2-a]pyridine-3-carboxamides was synthesized and screened against Mycobacterium tuberculosis H(37)Rv. The minimum inhibitory concentrations of 12 of these agents were <= 1 mu M against replicating bacteria and 5 compounds (9, 12, 16, 17, and 18) had MIC values <= 0.006 mu M. Compounds 13 and 18 were screened against a panel of MDR and XDR drug resistant clinical Mtb strains with the potency of 18 surpassing that of clinical candidate PA-824 by nearly 10-fold. The in vivo pharmacokinetics of compounds 13 and 18 were evaluated in male mice by oral (PO) and intravenous (IV) routes. These results indicate that readily synthesized imidazo[1,2-a]pyridine-3-carboxamides are an exciting new class of potent, selective anti-TB agents that merit additional development opportunities.