(S)-1-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-4-[1-methyl-1-(5-pyridin-4-yl-furan-2-yl)-ethyl]-piperazine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide | 342600-79-7

• 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: (S)-1-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-4-[1-methyl-1-(5-pyridin-4-yl-furan-2-yl)-ethyl]-piperazine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide
• 英文别名: (2S)-1-[(2S,4R)-4-benzyl-2-[tert-butyl(dimethyl)silyl]oxy-5-[[(3S,4S)-3-hydroxy-3,4-dihydro-2H-chromen-4-yl]amino]-5-oxopentyl]-4-[2-(5-pyridin-4-ylfuran-2-yl)propan-2-yl]-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide
• CAS: 342600-79-7
• 化学式: C₄₆H₆₀F₃N₅O₆Si
• 分子量: 864.093
• InChiKey: TXSJKCRJEMWEMF-SNWRNPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (S)-1-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-4-[1-methyl-1-(5-pyridin-4-yl-furan-2-yl)-ethyl]-piperazine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (αR,γS,2S)-N-((3S,4S)-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)-γ-hydroxy-4-[1-methyl-1-[5-(4-pyridinyl)-2-furanyl]ethyl]-α-(phenylmethyl)-2-[[(2,2,2-trifluoroethyl)amino]carbonyl]-1-piperazinepentanamide
  参考文献：
  名称：

  HIV protease inhibitors with picomolar potency against PI-Resistant HIV-1 by extension of the P3 substituent

  摘要：

  A biaryl pyridylfuran P-3 substituent on the hydroxyethylene isostere scaffold affords HIV protease inhibitors (PI's) with picomolar (IC50) potency against the protease enzymes from PI-resistant HIV-1 strains. Inclusion of a gem-dimethyl substituent afforded compound 3 with 100% oral bioavailability (dogs) and more than double the t(1/2) of indinavir. Inhibition of multiple P450 isoforms is dependent on the regiochemistry of the pyridyl nitrogen in these compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00475-x
• 作为产物：
  描述：

  4-(2-furyl)pyridine 在 lithium hydroxide 、 正丁基锂 、 tris(dibenzylideneacetone)dipalladium (0) 、 硫代水杨酸 、 水 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 乙二醇二甲醚 、 二氯甲烷 、 异丙醇 为溶剂， 生成 (S)-1-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-4-[1-methyl-1-(5-pyridin-4-yl-furan-2-yl)-ethyl]-piperazine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide
  参考文献：
  名称：

  HIV protease inhibitors with picomolar potency against PI-Resistant HIV-1 by extension of the P3 substituent

  摘要：

  A biaryl pyridylfuran P-3 substituent on the hydroxyethylene isostere scaffold affords HIV protease inhibitors (PI's) with picomolar (IC50) potency against the protease enzymes from PI-resistant HIV-1 strains. Inclusion of a gem-dimethyl substituent afforded compound 3 with 100% oral bioavailability (dogs) and more than double the t(1/2) of indinavir. Inhibition of multiple P450 isoforms is dependent on the regiochemistry of the pyridyl nitrogen in these compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00475-x

文献信息

• HIV protease inhibitors with picomolar potency against PI-Resistant HIV-1 by extension of the P3 substituent
  作者：Joseph L. Duffy、Thomas A. Rano、Nancy J. Kevin、Kevin T. Chapman、William A. Schleif、David B. Olsen、Mark Stahlhut、Carrie A. Rutkowski、Lawrence C. Kuo、Lixia Jin、Jiunn H. Lin、Emilio A. Emini、James R. Tata

  DOI：10.1016/s0960-894x(03)00475-x

  日期：2003.8

  A biaryl pyridylfuran P-3 substituent on the hydroxyethylene isostere scaffold affords HIV protease inhibitors (PI's) with picomolar (IC50) potency against the protease enzymes from PI-resistant HIV-1 strains. Inclusion of a gem-dimethyl substituent afforded compound 3 with 100% oral bioavailability (dogs) and more than double the t(1/2) of indinavir. Inhibition of multiple P450 isoforms is dependent on the regiochemistry of the pyridyl nitrogen in these compounds. (C) 2003 Elsevier Ltd. All rights reserved.