6-methyl-2-(trifluoromethyl)-imidazo[1,2-a]pyridine-3-carboxylic acid | 874830-67-8

• 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: 6-methyl-2-(trifluoromethyl)-imidazo[1,2-a]pyridine-3-carboxylic acid
• 英文别名: 6-Methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid；6-methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid
• CAS: 874830-67-8
• 化学式: C₁₀H₇F₃N₂O₂
• 分子量: 244.173
• InChiKey: VIYRKDXAKLBBAG-UHFFFAOYSA-N

物化性质

• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-methyl-2-(trifluoromethyl)-imidazo[1,2-a]pyridine-3-carboxylic acid 、 4-(甲砜基)苄胺盐酸盐 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 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以17%的产率得到6-methyl-N-(4-(methylsulfonyl)benzyl)-2-(trifluoromethyl)imidazo[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
• 作为产物：
  描述：

  2-氨基-5-甲基吡啶 在 sodium carbonate 、 lithium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 72.0h， 生成 6-methyl-2-(trifluoromethyl)-imidazo[1,2-a]pyridine-3-carboxylic acid
  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

• [EN] ANTIBACTERIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS
  申请人：JANSSEN SCIENCES IRELAND UNLIMITED CO

  公开号：WO2022194803A1

  公开（公告）日：2022-09-22

  The present invention relates to the compounds (I) wherein the integers are as defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of tuberculosis.

  本发明涉及化合物（I），其中整数如描述中所定义，并且这些化合物可以作为药物有用，例如用于治疗结核病。
• ANTIBACTERIAL COMPOUNDS
  申请人：Janssen Sciences Ireland Unlimited Company

  公开号：EP4028399A1

  公开（公告）日：2022-07-20
• 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.