6-甲基-2-(三氟甲基)咪唑并[1,2-a]吡啶-3-羧酸乙酯 | 420130-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 6-甲基-2-(三氟甲基)咪唑并[1,2-a]吡啶-3-羧酸乙酯
• 英文名称: ethyl 6-methyl-2-(trifluoromethyl)-imidazo[1,2-a]pyridine-3-carboxylate
• 英文别名: Ethyl 6-methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate；ethyl 6-methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate
• CAS: 420130-61-6
• 化学式: C₁₂H₁₁F₃N₂O₂
• 分子量: 272.227
• InChiKey: NDUPHWZTTHSDCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-甲基-2-(三氟甲基)咪唑并[1,2-a]吡啶-3-羧酸乙酯 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以98%的产率得到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
• 作为产物：
  描述：

  2-氨基-5-甲基吡啶 、 2-氯-4,4,4-三氟乙酰乙酸乙酯 在 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 36.0h， 以76%的产率得到6-甲基-2-(三氟甲基)咪唑并[1,2-a]吡啶-3-羧酸乙酯
  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

• 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.