(S)-tetrahydrofuran-3-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)butan-2-yl)carbamate | 1335386-86-1

• 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)-tetrahydrofuran-3-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)butan-2-yl)carbamate
• 英文别名: Yan-PI11；[(3S)-oxolan-3-yl] N-[(2S,3R)-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]-1-[4-[4-(trifluoromethoxy)phenyl]phenyl]butan-2-yl]carbamate
• CAS: 1335386-86-1
• 化学式: C₃₃H₃₉F₃N₂O₈S
• 分子量: 680.742
• InChiKey: WNFSFBAZUGMYBX-LHGWWSMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  4-iodo-L-phenylalanine 在 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 三光气 、 palladium 10% on activated carbon 、 diisopropylaminomagnesium bromide 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 magnesium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 (S)-tetrahydrofuran-3-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)butan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors

  摘要：

  A series of P1-substituted biaryl amprenavir derivatives was designed and synthesized. These compounds were evaluated for enzyme inhibition and antiviral activity in vitro. Several compounds showed highly efficient antiviral activity with EC50 values down to 0.10 nM, which are more potent than marketed HIV-1 protease inhibitors. Docking study indicated that 12c has similar binding mode to amprenavir with full occupancy in P1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.037

文献信息

• Synthesis and biological evaluation of novel amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors
  作者：Jianwei Yan、Ning Huang、Shukun Li、Liu-Meng Yang、Weiqiang Xing、Yong-Tang Zheng、Youhong Hu

  DOI：10.1016/j.bmcl.2012.01.037

  日期：2012.3

  A series of P1-substituted biaryl amprenavir derivatives was designed and synthesized. These compounds were evaluated for enzyme inhibition and antiviral activity in vitro. Several compounds showed highly efficient antiviral activity with EC50 values down to 0.10 nM, which are more potent than marketed HIV-1 protease inhibitors. Docking study indicated that 12c has similar binding mode to amprenavir with full occupancy in P1. (C) 2012 Elsevier Ltd. All rights reserved.