Ethyl 2-(aminomethyl)-4-methyl-1,3-thiazole-5-carboxylate | 120237-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 2-(aminomethyl)-4-methyl-1,3-thiazole-5-carboxylate
• CAS: 120237-87-8
• 化学式: C₈H₁₂N₂O₂S
• mdl: MFCD09904789
• 分子量: 200.261
• InChiKey: AQVCYUVTTLBJJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氯-5-(2,6-二甲氧基苯基)-1,2,4-三嗪 、 Ethyl 2-(aminomethyl)-4-methyl-1,3-thiazole-5-carboxylate 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 Ethyl 2-[[[5-(2,6-dimethoxyphenyl)-1,2,4-triazin-3-yl]amino]methyl]-4-methyl-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  Novel HldE-K Inhibitors Leading to Attenuated Gram Negative Bacterial Virulence

  摘要：

  We report here the optimization of an HldE kinase inhibitor to low nanomolar potency, which resulted in the identification of the first reported compounds active on selected E. coli strains. One of the most interesting candidates, compound 86, was shown to inhibit specifically bacterial I,PS heptosylation on efflux pump deleted E. coli strains. This compound did not interfere with E. coli bacterial growth (MIC > 32 mu g/mL) but sensitized this pathogen to hydrophobic antibiotics like macrolides normally inactive on Gram-negative bacteria. In addition, 86 could sensitize E. coli to serum complement killing. These results demonstrate that HldE kinase is a suitable target for drug discovery. They also pave the way toward novel possibilities of treating or preventing bloodstream infections caused by pathogenic Gram negative bacteria by inhibiting specific virulence factors.

  DOI：

  10.1021/jm301499r