3-羟基异恶唑-5-羧酸甲酯 | 1028260-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-羟基异恶唑-5-羧酸甲酯
• 英文名称: 3-hydroxyisoxazole-5-carboxylic acid methyl ester
• 英文别名: 2,3-dihydro-3-oxo-4-Isoxazolecarboxylic acid methyl ester；methyl 3-oxo-1,2-oxazole-4-carboxylate
• CAS: 1028260-93-6
• 化学式: C₅H₅NO₄
• 分子量: 143.099
• InChiKey: ROCWFFNVJQJWIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-羟基异恶唑-5-羧酸甲酯 、 (S)-1-BOC-2-氮杂环丁烷甲醇 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， 生成
  参考文献：
  名称：

  From α4β2 Nicotinic Ligands to the Discovery of σ1 Receptor Ligands: Pharmacophore Analysis and Rational Design

  摘要：

  Comparative analyses of the pharmacophoric elements required for sigma 1 and nicotinic ligands led to the identification of a potent and selective sigma 1 ligand (15). Compound 15 displayed high selectivity for the sigma 1 receptor (K-i, sigma 1 = 4.1 nM; K-i, sigma 2 = 1312 nM) with moderate binding affinity for the DAT (K-i = 373 nM) and NET (K-i = 203 nM) in the PDSP broad screening panel of common CNS neurotransmitter transporters and receptors. The key finding in this present work is that a subtle structural modification could be used as a tool to switch a ligand's selectivity between nAChRs and sigma receptors.

  DOI：

  10.1021/ml3002715

文献信息

• From α4β2 Nicotinic Ligands to the Discovery of σ1 Receptor Ligands: Pharmacophore Analysis and Rational Design
  作者：Li-Fang Yu、Han-Kun Zhang、Hendra Gunosewoyo、Alan P. Kozikowski

  DOI：10.1021/ml3002715

  日期：2012.12.13

  Comparative analyses of the pharmacophoric elements required for sigma 1 and nicotinic ligands led to the identification of a potent and selective sigma 1 ligand (15). Compound 15 displayed high selectivity for the sigma 1 receptor (K-i, sigma 1 = 4.1 nM; K-i, sigma 2 = 1312 nM) with moderate binding affinity for the DAT (K-i = 373 nM) and NET (K-i = 203 nM) in the PDSP broad screening panel of common CNS neurotransmitter transporters and receptors. The key finding in this present work is that a subtle structural modification could be used as a tool to switch a ligand's selectivity between nAChRs and sigma receptors.