<3(S),4(S)>-2,4,5-trideoxy-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-difluoro-5-<4-(2-methoxy-2-oxoethoxy)phenyl>-N-(phenylmethyl)-L-glycero-pentonamide | 158268-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <3(S),4(S)>-2,4,5-trideoxy-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-difluoro-5-<4-(2-methoxy-2-oxoethoxy)phenyl>-N-(phenylmethyl)-L-glycero-pentonamide
• CAS: 158268-38-3
• 化学式: C₂₆H₃₂F₂N₂O₇
• 分子量: 522.546
• InChiKey: WZDWZCREHUUVKC-UNMCSNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  123.19
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  <3(S),4(S)>-2,4,5-trideoxy-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-difluoro-5-<4-(2-methoxy-2-oxoethoxy)phenyl>-N-(phenylmethyl)-L-glycero-pentonamide 、 三氟乙酸 反应 2.0h， 生成 [4-((S)-2-Amino-4-benzylcarbamoyl-4,4-difluoro-3-hydroxy-butyl)-phenoxy]-acetic acid methyl ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Design, Synthesis, and Conformational Analysis of a Novel Macrocyclic HIV-Protease Inhibitor

  摘要：

  Design modifications to the lead HnT-PR inhibitor 1 (MDL 73,669, K-i = 5 nM) have been postulated based on a computational model of the 1/HIV-PR complex. A novel macrocyclic inhibitor 8 (MDL 104,168) wherein the P-1 and P-3 Side chains of the original acyclic inhibitor have been joined retains good biological activity (K-i = 20 nM). NMR analysis of the precursor alcohol (S)-7 shows the conformation of the cyclic region to be very similar to that observed in the enzyme-bound 8 as determined by the computational model. Consistency of the computational model with NMR data and in vacuo molecular dynamics simulations provide the basis for postulating further modifications of the cyclic inhibitor expected to optimize its interactions with HIV-PR.

  DOI：

  10.1021/jm00048a004
• 作为产物：
  描述：

  [(1S,2S)-3-Benzylcarbamoyl-1-(4-benzyloxy-benzyl)-3,3-difluoro-2-hydroxy-propyl]-carbamic acid tert-butyl ester 在 钯 甲酸 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 78.25h， 生成 <3(S),4(S)>-2,4,5-trideoxy-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-difluoro-5-<4-(2-methoxy-2-oxoethoxy)phenyl>-N-(phenylmethyl)-L-glycero-pentonamide
  参考文献：
  名称：

  Design, Synthesis, and Conformational Analysis of a Novel Macrocyclic HIV-Protease Inhibitor

  摘要：

  Design modifications to the lead HnT-PR inhibitor 1 (MDL 73,669, K-i = 5 nM) have been postulated based on a computational model of the 1/HIV-PR complex. A novel macrocyclic inhibitor 8 (MDL 104,168) wherein the P-1 and P-3 Side chains of the original acyclic inhibitor have been joined retains good biological activity (K-i = 20 nM). NMR analysis of the precursor alcohol (S)-7 shows the conformation of the cyclic region to be very similar to that observed in the enzyme-bound 8 as determined by the computational model. Consistency of the computational model with NMR data and in vacuo molecular dynamics simulations provide the basis for postulating further modifications of the cyclic inhibitor expected to optimize its interactions with HIV-PR.

  DOI：

  10.1021/jm00048a004