((S)-1-{(2S,4R)-4-[4-(3-Hydroxy-propyl)-benzyl]-5-oxo-tetrahydro-furan-2-yl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester | 141221-99-0

• 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: ((S)-1-{(2S,4R)-4-[4-(3-Hydroxy-propyl)-benzyl]-5-oxo-tetrahydro-furan-2-yl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S)-1-[(2S,4R)-4-[[4-(3-hydroxypropyl)phenyl]methyl]-5-oxooxolan-2-yl]-2-phenylethyl]carbamate
• CAS: 141221-99-0
• 化学式: C₂₇H₃₅NO₅
• 分子量: 453.579
• InChiKey: YKDQMTHBTSEUOJ-SGNDLWITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((S)-1-{(2S,4R)-4-[4-(3-Hydroxy-propyl)-benzyl]-5-oxo-tetrahydro-furan-2-yl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester 在 咪唑 、 lithium hydroxide 、 四丁基氟化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 118.0h， 生成 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-(1,1-dimethylethoxycarbonyl)amino-4(S)-hydroxy-6-phenyl-2(R)-(4-(3-(2-methoxyethoxy)methoxypropyl)-phenyl)methylhexanamide
  参考文献：
  名称：

  HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: An investigation into the role of the P1' side chain on structure-activity

  摘要：

  A systematic investigation was undertaken to determine the role of the P1' sidechain in a series of hydroxyethylene isostere based inhibitors of HIV-1 protease. Substitution and homologation of the benzyl P1' side chain of the Phe-Phe isostere based pseudo peptides 1 (L-682,679) and 2 (L-685,434) with various heteroalkyl groups leads to a series of extremely potent inhibitors of the enzyme. Several examples of the most potent inhibitors were very effective in an ex vivo cell based viral spread assay using human H9 T-lymphocytes and the IIIb isolate of HIV-1. Compound 19 is 120 times more potent than 1 and 16 times more potent than 2 in inhibiting the spread of infection in this assay.

  DOI：

  10.1021/jm00088a004
• 作为产物：
  描述：

  (S)-5-((S)-1-tert-Butoxycarbonylamino-2-phenyl-ethyl)-3-[4-(3-hydroxy-propyl)-benzyl]-2-oxo-tetrahydro-furan-3-carboxylic acid 以 甲苯 为溶剂， 反应 24.0h， 生成 ((S)-1-{(2S,4R)-4-[4-(3-Hydroxy-propyl)-benzyl]-5-oxo-tetrahydro-furan-2-yl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: An investigation into the role of the P1' side chain on structure-activity

  摘要：

  A systematic investigation was undertaken to determine the role of the P1' sidechain in a series of hydroxyethylene isostere based inhibitors of HIV-1 protease. Substitution and homologation of the benzyl P1' side chain of the Phe-Phe isostere based pseudo peptides 1 (L-682,679) and 2 (L-685,434) with various heteroalkyl groups leads to a series of extremely potent inhibitors of the enzyme. Several examples of the most potent inhibitors were very effective in an ex vivo cell based viral spread assay using human H9 T-lymphocytes and the IIIb isolate of HIV-1. Compound 19 is 120 times more potent than 1 and 16 times more potent than 2 in inhibiting the spread of infection in this assay.

  DOI：

  10.1021/jm00088a004