2-phenyl-4-(phenylmethyl)-5-oxazolepropanoic acid | 82354-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-4-(phenylmethyl)-5-oxazolepropanoic acid
• CAS: 82354-93-6
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: IOTYHTKAEHBLFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  methyl 2-phenyl-4-(phenylmethyl)-5-oxazolepropanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以76%的产率得到2-phenyl-4-(phenylmethyl)-5-oxazolepropanoic acid
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors: modifications of a tripeptide analog

  摘要：

  Modified nonhydrolyzable tripeptide analogues of (S)-1-[5-(benzoylamino)-1,4-dioxo-6-phenylhexyl]-L-proline (1), designed to impart oral angiotensin converting enzyme (ACE) inhibitory activity, were made and evaluated in vivo and in vitro. The N-methyl and C5-methyl analogues of 1 were inactive. Insertion of heteroatoms (O, S, NH) into the C--C chain of 1 gave a series of compounds with high in vitro activity in the guinea pig serum ACE assay. The O-analogue was the most potent with an IC50 = 4.4 x 10(-9) M compared to 1 with an IC50 = 3.2 x 10(-9) M. The structure-activity relationships in this series of compounds lead one to speculate that the heteroatom provides an additional binding site to the surface of the enzyme; however, these compounds were inactive when tested for antihypertensive activity in the renal hypertensive rat at 30 mg/kg by the oral route (captopril is active at 1.0 mg/kg po).

  DOI：

  10.1021/jm00350a023