| 1204484-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1204484-57-0
• 化学式: C₂₈H₃₂NO₆P
• 分子量: 509.539
• InChiKey: BGHGJBQCLKNILQ-FXDYGKIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  112.93
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  、 (S)-alpha-氨基-1H-吲哚-3-丙酰胺 以75%的产率得到
  参考文献：
  名称：

  Conformational and Solvation Studies via Computer Simulation of the Novel Large Scale Diastereoselectively Synthesized Phosphinic MMP Inhibitor RXP03 Diluted in Selected Solvents

  摘要：

  Structure-activity relationship studies, regarding the influence of side chains of phosphinic pseudotripeptidic inhibitors on matrix metalloproteinases (MMPs), provided potent and selective inhibitors for this family of structurally and functionally related proteases. Among them, phosphinic pseudopeptide CbzPhe psi [P(O)(OH)CH2] phenylpropyl TrpNH(2), known as RXP03, has been extensively used for in vivo and in vitro studies so far. The large quantities of RXP03 required for in vivo studies, as well as the necessity for diastereoisomeric purity, motivated us to further explore and develop an efficient synthetic methodology, which allows separation of the four diastereoisomers of RXP03 based on the astonishing observed differences in solubility of the four isomers In Various solvents. This fact prompted us to examine theoretically the conformational differences of these four isomers via computer simulations in the solvents used experimentally. Given the fact that the four examined diastereoisomeric forms of the phosphinic peptides exhibit different behavior in terms of potency and selectivity profiles toward zinc-metalloproteases, this theoretical study provides valuable information on the conformation of phosphinic inhibitors and therefore improves the design and synthesis of active Structures. The differences ill Solubility of RXP03 diastereoisomers in the used solvents were examined in terms of intra- and intermolecular Structure. It is Found that the different solubility of the RRS and RSS diastereoisomers in EtOH is a result of the different number of hydrogen bonds formed by each isomer with EtOH molecules. In the case of SRS and SSS in Et2O, their different Solubility might be attributed to the different intramolecular hydrogen bonds formed on these diastereoisomers.

  DOI：

  10.1021/jp903830v
• 作为产物：
  描述：

  ((R)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)(2-(ethoxycarbonyl)-5-phenylpentyl)phosphinic acid 以98%的产率得到
  参考文献：
  名称：

  Conformational and Solvation Studies via Computer Simulation of the Novel Large Scale Diastereoselectively Synthesized Phosphinic MMP Inhibitor RXP03 Diluted in Selected Solvents

  摘要：

  Structure-activity relationship studies, regarding the influence of side chains of phosphinic pseudotripeptidic inhibitors on matrix metalloproteinases (MMPs), provided potent and selective inhibitors for this family of structurally and functionally related proteases. Among them, phosphinic pseudopeptide CbzPhe psi [P(O)(OH)CH2] phenylpropyl TrpNH(2), known as RXP03, has been extensively used for in vivo and in vitro studies so far. The large quantities of RXP03 required for in vivo studies, as well as the necessity for diastereoisomeric purity, motivated us to further explore and develop an efficient synthetic methodology, which allows separation of the four diastereoisomers of RXP03 based on the astonishing observed differences in solubility of the four isomers In Various solvents. This fact prompted us to examine theoretically the conformational differences of these four isomers via computer simulations in the solvents used experimentally. Given the fact that the four examined diastereoisomeric forms of the phosphinic peptides exhibit different behavior in terms of potency and selectivity profiles toward zinc-metalloproteases, this theoretical study provides valuable information on the conformation of phosphinic inhibitors and therefore improves the design and synthesis of active Structures. The differences ill Solubility of RXP03 diastereoisomers in the used solvents were examined in terms of intra- and intermolecular Structure. It is Found that the different solubility of the RRS and RSS diastereoisomers in EtOH is a result of the different number of hydrogen bonds formed by each isomer with EtOH molecules. In the case of SRS and SSS in Et2O, their different Solubility might be attributed to the different intramolecular hydrogen bonds formed on these diastereoisomers.

  DOI：

  10.1021/jp903830v