5-ethoxy-2-benzyl-oxazole-4-carboxylic acid ethyl ester | 872806-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-ethoxy-2-benzyl-oxazole-4-carboxylic acid ethyl ester
• 英文别名: 5-Aethoxy-2-benzyl-oxazol-4-carbonsaeure-aethylester；Ethyl 2-benzyl-5-ethoxy-1,3-oxazole-4-carboxylate
• CAS: 872806-16-1
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: FRVNBXKGYINUAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-ethoxy-2-benzyl-oxazole-4-carboxylic acid ethyl ester 在 1,4-二氧六环 、 氢氧化钾 、 氯化亚砜 、 氯仿 作用下， 生成 2-benzyl-5-chloro-oxazole-4-carboxylic acid
  参考文献：
  名称：

  Cornforth, Chemistry of Penicillin

  摘要：

  DOI：
• 作为产物：
  描述：

  phenylacetylaminomalonic acid diethyl ester 在 三氟乙酸酐 作用下， 以 2,3,4-三氟甲苯 为溶剂， 生成 5-ethoxy-2-benzyl-oxazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Structure–activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors

  摘要：

  Human rhinovirus 3C protease (HRV 3C(pro)) is known to be a promising target for development of therapeutic agents against the common cold because of the importance of the protease in viral replication as well as its expression in a large number of serotypes. To explore non-peptidic inhibitors of HRV 3C(pro), a series of novel heteroaromatic esters was synthesized and evaluated for inhibitory activity against HRV 3C(pro), to determine the structure-activity relationships. The most potent inhibitor, 7, with a 5-bromopyridinyl group, had an IC50 value of 80 nM. In addition, the binding mode of a novel analog, 19, with the 4-hydroxyquinolinone moiety, was explored by molecular docking, suggesting a new interaction in the S1 pocket. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.114