Ethyl 2-Amino-4-(methoxymethyl)thiazole-5-carboxylate | 905807-82-1

• 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-Amino-4-(methoxymethyl)thiazole-5-carboxylate
• 英文别名: ethyl 2-amino-4-(methoxymethyl)-1,3-thiazole-5-carboxylate
• CAS: 905807-82-1
• 化学式: C₈H₁₂N₂O₃S
• 分子量: 216.261
• InChiKey: SSPWUMHZSKIWSU-UHFFFAOYSA-N

物化性质

• 沸点：
  361.8±32.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  Ethyl 2-Amino-4-(methoxymethyl)thiazole-5-carboxylate 在 t-butyl nitrite 、 copper dichloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以95%的产率得到ethyl 2-chloro-4-(methoxymethyl)thiazole-5-carboxylate
  参考文献：
  名称：

  Optimization of Pyrrolamide Topoisomerase II Inhibitors Toward Identification of an Antibacterial Clinical Candidate (AZD5099)

  摘要：

  AZD5099 (compound 63) is an antibacterial agent that entered phase 1 clinical trials targeting infections caused by Gram-positive and fastidious Gram-negative bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramolecular hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound 63 showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency versus the drug was low, and reports of clinical resistance due to alteration of the target are few. Hence, 63 could offer a novel treatment for serious issues of resistance to currently used antibacterials.

  DOI：

  10.1021/jm500462x