(2S)-1-[(2S,4S)-2-hydroxy-5-[[(3S,4S)-3-hydroxychroman-4-yl]amino]-5-oxo-4-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pentyl]-4-[1-[5-(5-methoxy-3-pyridyl)oxazol-2-yl]-1-methyl-ethyl]-N-(2,2,2-trifluoroethyl)piperazine-2-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: (2S)-1-[(2S,4S)-2-hydroxy-5-[[(3S,4S)-3-hydroxychroman-4-yl]amino]-5-oxo-4-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pentyl]-4-[1-[5-(5-methoxy-3-pyridyl)oxazol-2-yl]-1-methyl-ethyl]-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide
• 英文别名: (2S)-1-[(2S,4S)-2-hydroxy-5-[[(3S,4S)-3-hydroxy-3,4-dihydro-2H-chromen-4-yl]amino]-5-oxo-4-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pentyl]-4-[2-[5-(5-methoxypyridin-3-yl)-1,3-oxazol-2-yl]propan-2-yl]-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide
• 化学式: C₄₂H₄₇F₃N₈O₈
• 分子量: 848.879
• InChiKey: QAWJSYUSNVBIAR-KCMFSSCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  61
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  cis-4-amino-3-chromanol 在 咪唑 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 重铬酸吡啶 、 四丁基氟化铵 、 碳酸氢钠 、 1-羟基苯并三唑 、 对甲苯磺酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 、 lithium hexamethyldisilazane 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 2-甲基-2-丁醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (2S)-1-[(2S,4S)-2-hydroxy-5-[[(3S,4S)-3-hydroxychroman-4-yl]amino]-5-oxo-4-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pentyl]-4-[1-[5-(5-methoxy-3-pyridyl)oxazol-2-yl]-1-methyl-ethyl]-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide
  参考文献：
  名称：

  P1′ oxadiazole protease inhibitors with excellent activity against native and protease inhibitor-resistant HIV-1

  摘要：

  HIV-1 protease inhibitors (PI's) bearing 1,3,4-oxadiazoles at the P1' position were prepared by a novel method involving the diastereoselective installation of a carboxylic acid and conversion to the P1' heterocycle. The compounds are picomolar inhibitors of native HIV-1 protease, with most of the compounds maintaining excellent antiviral activity against a panel of PI-resistant strains. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.092

文献信息

• P1′ oxadiazole protease inhibitors with excellent activity against native and protease inhibitor-resistant HIV-1
  作者：Ronald M. Kim、Elizabeth A. Rouse、Kevin T. Chapman、William A. Schleif、David B. Olsen、Mark Stahlhut、Carrie A. Rutkowski、Emilio A. Emini、James R. Tata

  DOI：10.1016/j.bmcl.2004.06.092

  日期：2004.9

  HIV-1 protease inhibitors (PI's) bearing 1,3,4-oxadiazoles at the P1' position were prepared by a novel method involving the diastereoselective installation of a carboxylic acid and conversion to the P1' heterocycle. The compounds are picomolar inhibitors of native HIV-1 protease, with most of the compounds maintaining excellent antiviral activity against a panel of PI-resistant strains. (C) 2004 Elsevier Ltd. All rights reserved.