2-(Dimethoxy-phosphoryl)-3-naphthalen-2-yl-propionic acid | 208169-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(Dimethoxy-phosphoryl)-3-naphthalen-2-yl-propionic acid
• CAS: 208169-58-8
• 化学式: C₁₅H₁₇O₅P
• 分子量: 308.271
• InChiKey: BJHSJOJXMKEMMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(Dimethoxy-phosphoryl)-3-naphthalen-2-yl-propionic acid 在 palladium on activated charcoal 二苯基磷酸 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 生成 [(R)-1-((S)-2-Formylamino-3-methyl-butyrylamino)-2-naphthalen-2-yl-ethyl]-phosphonic acid dimethyl ester
  参考文献：
  名称：

  Macrocyclic Inhibitors of Penicillopepsin. 1. Design, Synthesis, and Evaluation of an Inhibitor Bridged between P1 and P3

  摘要：

  The macrocyclic peptidyl phosphonate 1-L was designed on the basis of the conformation of an acyclic analogue (4) bound to the aspartic protease penicillopepsin. This material and the two acyclic comparison compounds 2-L and 3 were synthesized and evaluated as inhibitors; their binding affinity was found to be inversely related to the degree of conformational flexibility across the series: 3 (K-i = 110 mu M), 2-L (K-i = 7.6 mu M), 1-L (K-i = 0.80 mu M). NMR methods in conjunction with molecular modeling were used to assign the stereochemical configurations of the precursor 16-L and its diastereomer 16-D and to determine the solution conformations of the macrocyclic ring systems. The conformation of the peptide backbone in 1-L closely approximates that desired for a mimic of the lead inhibitor 4, and it appears that the low-energy conformation of 1-L can be accommodated in the pencillopepsin active site without significant distortion.

  DOI：

  10.1021/ja973715j
• 作为产物：
  描述：

  Tert-butyl 2-dimethoxyphosphoryl-3-naphthalen-2-ylpropanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-(Dimethoxy-phosphoryl)-3-naphthalen-2-yl-propionic acid
  参考文献：
  名称：

  Macrocyclic Inhibitors of Penicillopepsin. 1. Design, Synthesis, and Evaluation of an Inhibitor Bridged between P1 and P3

  摘要：

  The macrocyclic peptidyl phosphonate 1-L was designed on the basis of the conformation of an acyclic analogue (4) bound to the aspartic protease penicillopepsin. This material and the two acyclic comparison compounds 2-L and 3 were synthesized and evaluated as inhibitors; their binding affinity was found to be inversely related to the degree of conformational flexibility across the series: 3 (K-i = 110 mu M), 2-L (K-i = 7.6 mu M), 1-L (K-i = 0.80 mu M). NMR methods in conjunction with molecular modeling were used to assign the stereochemical configurations of the precursor 16-L and its diastereomer 16-D and to determine the solution conformations of the macrocyclic ring systems. The conformation of the peptide backbone in 1-L closely approximates that desired for a mimic of the lead inhibitor 4, and it appears that the low-energy conformation of 1-L can be accommodated in the pencillopepsin active site without significant distortion.

  DOI：

  10.1021/ja973715j