{7-[2-Benzyloxycarbonylamino-2-(dimethoxy-phosphoryl)-ethyl]-naphthalen-1-yl}-acetic acid methyl ester | 208169-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: {7-[2-Benzyloxycarbonylamino-2-(dimethoxy-phosphoryl)-ethyl]-naphthalen-1-yl}-acetic acid methyl ester
• CAS: 208169-41-9
• 化学式: C₂₅H₂₈NO₇P
• 分子量: 485.474
• InChiKey: BTRYJHUBXOGNLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  {7-[2-Benzyloxycarbonylamino-2-(dimethoxy-phosphoryl)-ethyl]-naphthalen-1-yl}-acetic acid methyl ester 在 palladium on activated charcoal 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 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 {7-[2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-2-(dimethoxy-phosphoryl)-ethyl]-naphthalen-1-yl}-acetic acid methyl 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：

  (7-Bromo-3,4-dihydro-naphthalen-1-yl)-acetic acid ethyl ester 在 sodium periodate 、 四氧化锇 、 四(三苯基膦)钯 、 溴 、 potassium carbonate 、 溶剂黄146 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 水 、 丙酮 、 苯 为溶剂， 反应 51.5h， 生成 {7-[2-Benzyloxycarbonylamino-2-(dimethoxy-phosphoryl)-ethyl]-naphthalen-1-yl}-acetic acid methyl 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