3-((2S,3R)-1-(benzo[b]thiophen-2-yl)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxybutan-2-ylcarbamoyl)-2-methylphenyl acetate | 1208246-96-1

• 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: 3-((2S,3R)-1-(benzo[b]thiophen-2-yl)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxybutan-2-ylcarbamoyl)-2-methylphenyl acetate
• 英文别名: [3-[[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-1-(1-benzothiophen-2-yl)-3-hydroxybutan-2-yl]carbamoyl]-2-methylphenyl] acetate
• CAS: 1208246-96-1
• 化学式: C₃₆H₄₇N₃O₅S
• 分子量: 633.852
• InChiKey: BLBBPDVQBZXYEO-WWBZPSCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-((2S,3R)-1-(benzo[b]thiophen-2-yl)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxybutan-2-ylcarbamoyl)-2-methylphenyl acetate 在 甲醇 、 sodium 作用下， 以95%的产率得到(3S,4aS,8aS)-2-((2R,3s)-4-(benzo[b]thiophen-2-yl)-2-hydroxy-3-(3-hydroxy-2-methylbenzamido)butyl)-N-tert-butyldecahydroisoquinoline-3-carboxamide
  参考文献：
  名称：

  Synthesis of New Thienyl Ring Containing HIV-1 Protease Inhibitors: Promising Preliminary Pharmacological Evaluation against Recombinant HIV-1 Proteases

  摘要：

  A series of new thienyl ring containing analogues of nelfinavir and saquinavir with different Substitution patterns were synthesized from suitable enantiopure diols. Their inhibitory activity against wild type recombinant HIV-1 protease was evaluated. In general thienyl groups spaced from the core by a methylene group gave products showing IC(50) in the nanomolar range, Irrespective of the type and the substitution pattern of the heterocycle. The range of activity of the two most active compounds is substantially maintained or even Increased against two commonly selected mutants, under drug pressure, Such as V32I and V82A.

  DOI：

  10.1021/jm900846f
• 作为产物：
  描述：

  (3S,4aS,8aS)-2-((2R,3S)-3-amino-4-(benzo[b]thiophen-2-yl)-2-hydroxybutyl)-N-tertbutyldecahydroisoquinoline-3-carboxamide 、 2-甲基-3-乙酰氧基苯甲酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到3-((2S,3R)-1-(benzo[b]thiophen-2-yl)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxybutan-2-ylcarbamoyl)-2-methylphenyl acetate
  参考文献：
  名称：

  Synthesis of New Thienyl Ring Containing HIV-1 Protease Inhibitors: Promising Preliminary Pharmacological Evaluation against Recombinant HIV-1 Proteases

  摘要：

  A series of new thienyl ring containing analogues of nelfinavir and saquinavir with different Substitution patterns were synthesized from suitable enantiopure diols. Their inhibitory activity against wild type recombinant HIV-1 protease was evaluated. In general thienyl groups spaced from the core by a methylene group gave products showing IC(50) in the nanomolar range, Irrespective of the type and the substitution pattern of the heterocycle. The range of activity of the two most active compounds is substantially maintained or even Increased against two commonly selected mutants, under drug pressure, Such as V32I and V82A.

  DOI：

  10.1021/jm900846f