(R)-phenyl-3-oxo-4-[(phenoxycarbonyl)-amino]isoxazolidine-2-carboxylate | 1436857-95-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-phenyl-3-oxo-4-[(phenoxycarbonyl)-amino]isoxazolidine-2-carboxylate
• 英文别名: phenyl (4R)-3-oxo-4-(phenoxycarbonylamino)-1,2-oxazolidine-2-carboxylate
• CAS: 1436857-95-2
• 化学式: C₁₇H₁₄N₂O₆
• 分子量: 342.308
• InChiKey: UGUCUEVJRPCFTP-CQSZACIVSA-N

物化性质

• 熔点：
  159-160 °C
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氯甲酸苯酯 、 D-环丝氨酸 在 碳酸氢钠 作用下， 反应 15.0h， 以85%的产率得到(R)-phenyl-3-oxo-4-[(phenoxycarbonyl)-amino]isoxazolidine-2-carboxylate
  参考文献：
  名称：

  Pharmacophore Assessment Through 3-D QSAR: Evaluation of the Predictive Ability on New Derivatives by the Application on a Series of Antitubercular Agents

  摘要：

  Pharmacophoric mapping is a useful procedure to frame, especially, when crystallographic receptor structures are unavailable as in ligand-based studies, the hypothetical site of interaction. In this study, 71 pyrrole derivatives active against M. tuberculosis, were used to derive through a recent new 3-D QSAR protocol; 3-D QSAutogrid/R, several predictive 3-D QSAR models on compounds aligned by a previously reported pharmacophoric application. A final multiprobe (MP) 3-D QSAR model was then obtained configuring itself as a tool to derive pharmacophoric quantitative models. To stress the applicability of the described models, an external test set of unrelated and newly synthesized series of R-4-amino-3-isoxazolidinone derivatives found to be active at micromolar level against M. tuberculosis was used, and the predicted bioactivities were in good agreement with the experimental values. The 3-D QSAutogrid/R procedure proved to be able to correlate by a single multi-informative scenario the,different activity molecular profiles thus confirming its usefulness in the rational drug design approach.

  DOI：

  10.1021/ci400132q

文献信息

• Pharmacophore Assessment Through 3-D QSAR: Evaluation of the Predictive Ability on New Derivatives by the Application on a Series of Antitubercular Agents
  作者：Laura Friggeri、Flavio Ballante、Rino Ragno、Ira Musmuca、Daniela De Vita、Fabrizio Manetti、Mariangela Biava、Luigi Scipione、Roberto Di Santo、Roberta Costi、Marta Feroci、Silvano Tortorella

  DOI：10.1021/ci400132q

  日期：2013.6.24

  Pharmacophoric mapping is a useful procedure to frame, especially, when crystallographic receptor structures are unavailable as in ligand-based studies, the hypothetical site of interaction. In this study, 71 pyrrole derivatives active against M. tuberculosis, were used to derive through a recent new 3-D QSAR protocol; 3-D QSAutogrid/R, several predictive 3-D QSAR models on compounds aligned by a previously reported pharmacophoric application. A final multiprobe (MP) 3-D QSAR model was then obtained configuring itself as a tool to derive pharmacophoric quantitative models. To stress the applicability of the described models, an external test set of unrelated and newly synthesized series of R-4-amino-3-isoxazolidinone derivatives found to be active at micromolar level against M. tuberculosis was used, and the predicted bioactivities were in good agreement with the experimental values. The 3-D QSAutogrid/R procedure proved to be able to correlate by a single multi-informative scenario the,different activity molecular profiles thus confirming its usefulness in the rational drug design approach.