ethyl 5-oxo-2H-1,2-oxazole-3-carboxylate | 88393-81-1

• 物质功能分类: 医药中间体
• 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 5-oxo-2H-1,2-oxazole-3-carboxylate
• 英文别名: 3-Ethoxycarbonyl-5-hydroxyisoxazol；5-hydroxyisoxazole-3-carboxylic acid ethyl ester
• CAS: 88393-81-1
• 化学式: C₆H₇NO₄
• 分子量: 157.126
• InChiKey: YDNVZHNBNHOKMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.56
• 氢给体数：
  1.0
• 氢受体数：
  5.0

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (S)-1-BOC-2-氮杂环丁烷甲醇 、 ethyl 5-oxo-2H-1,2-oxazole-3-carboxylate 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到5-[(1-(tert-butoxycarbonyl)-2(S)-azetidinyl)methoxy]-isoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Identification of Novel α4β2-Nicotinic Acetylcholine Receptor (nAChR) Agonists Based on an Isoxazole Ether Scaffold that Demonstrate Antidepressant-like Activity

  摘要：

  There is considerable evidence to support the hypothesis that the blockade of nAChR is responsible for the antidepressant action of nicotinic ligands. The nicotinic acetylcholine receptor (nAChR) antagonist, mecamylamine, has been shown to be an effective add-on in patients that do not respond to selective serotonin reuptake inhibitors. This suggests that nAChR ligands may address an unmet clinical need by providing relief from depressive symptoms in refractory patients. In this study, a new series of nAChR ligands based on an isoxazole-ether scaffold have been designed and synthesized for binding and functional assays. Preliminary structure-activity relationship (SAR) efforts identified a lead compound 43, which possesses potent antidepressant-like activity (1 mg/kg, IP; 5 mg/kg, PO) in the classical mouse forced swim test. Early stage absorption, distribution, metabolism, excretion, and toxicity (ADME-Tox) studies also suggested favorable drug-like properties, and broad screening toward other common neurotransmitter receptors indicated that compound 43 is highly selective for nAChRs over the other 45 neurotransmitter receptors and transporters tested.

  DOI：

  10.1021/jm201301h