N-tert-butyl-decahydro-2-[2-(R)-hydroxy-3(S)-[[N-[3-(4-hydroxyphenyl)-propionyl]-L-asparaginyl]amino]-4-phenylbutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-tert-butyl-decahydro-2-[2-(R)-hydroxy-3(S)-[[N-[3-(4-hydroxyphenyl)-propionyl]-L-asparaginyl]amino]-4-phenylbutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide
• 英文别名: (2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[3-(4-hydroxyphenyl)propanoylamino]butanediamide
• 化学式: C₃₇H₅₃N₅O₆
• 分子量: 663.858
• InChiKey: DPGDQNYVROQXOW-AOGLXMCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-decahydro-2-[2-(R)-hydroxy-3(S)-[[N-[3-(4-hydroxyphenyl)-propionyl]-L-asparaginyl]amino]-4-phenylbutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide 在 sodium iodide 、 chloroamine-T 作用下， 以 sodium hydroxide 、 phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.02h， 以21%的产率得到N-tert.butyl-decahydro-2-[2-(R)-hydroxy-3(S)-[[N-[3-(3-125I-iodo-4-hydroxyphenyl)-propionyl]-L-asparaginyl]amino]-4-phenylbutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide
  参考文献：
  名称：

  The synthesis of labelled forms of saquinavir

  摘要：

  The development of the HIV-protease inhibitor, saquinavir (Ro 31-8959), required a range of analytical methods for the measurement of the parent drug and drug-related material in biological fluids. This paper describes the synthesis of 14-carbon and tritium labelled compounds used for in vivo and in vitro investigations of the absorption and disposition of saquinavir in animals and man. It also discusses the preparation of saquinavir labelled with deuterium and stable isotopes of carbon and nitrogen. These forms of the drug were needed for bioequivalence studies in which HPLC/MS/MS was employed for the measurement of plasma concentrations. Finally, the synthesis of a 125-iodine labelled tracer used in a radioimmunoassay for saquinavir is described.

  DOI：

  10.1002/(sici)1099-1344(199812)41:12<1103::aid-jlcr157>3.0.co;2-m
• 作为产物：
  描述：

  2-<3(S)-<amino>-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide 在 palladium on activated charcoal N-乙基吗啉 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 75.5h， 生成 N-tert-butyl-decahydro-2-[2-(R)-hydroxy-3(S)-[[N-[3-(4-hydroxyphenyl)-propionyl]-L-asparaginyl]amino]-4-phenylbutyl]-(4aS,8aS)-isoquinoline-3(S)-carboxamide
  参考文献：
  名称：

  The synthesis of labelled forms of saquinavir

  摘要：

  The development of the HIV-protease inhibitor, saquinavir (Ro 31-8959), required a range of analytical methods for the measurement of the parent drug and drug-related material in biological fluids. This paper describes the synthesis of 14-carbon and tritium labelled compounds used for in vivo and in vitro investigations of the absorption and disposition of saquinavir in animals and man. It also discusses the preparation of saquinavir labelled with deuterium and stable isotopes of carbon and nitrogen. These forms of the drug were needed for bioequivalence studies in which HPLC/MS/MS was employed for the measurement of plasma concentrations. Finally, the synthesis of a 125-iodine labelled tracer used in a radioimmunoassay for saquinavir is described.

  DOI：

  10.1002/(sici)1099-1344(199812)41:12<1103::aid-jlcr157>3.0.co;2-m

文献信息

• The synthesis of labelled forms of saquinavir
  作者：H. R. Wiltshire、K. J. Prior、J. Dhesi、F. Trach、M. Schlageter、H. Schönenberger

  DOI：10.1002/(sici)1099-1344(199812)41:12<1103::aid-jlcr157>3.0.co;2-m

  日期：1998.12

  The development of the HIV-protease inhibitor, saquinavir (Ro 31-8959), required a range of analytical methods for the measurement of the parent drug and drug-related material in biological fluids. This paper describes the synthesis of 14-carbon and tritium labelled compounds used for in vivo and in vitro investigations of the absorption and disposition of saquinavir in animals and man. It also discusses the preparation of saquinavir labelled with deuterium and stable isotopes of carbon and nitrogen. These forms of the drug were needed for bioequivalence studies in which HPLC/MS/MS was employed for the measurement of plasma concentrations. Finally, the synthesis of a 125-iodine labelled tracer used in a radioimmunoassay for saquinavir is described.