(S)-4-[Cyano-methyl-(5-pyridin-4-yl-furan-2-yl)-methyl]-piperazine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide | 342600-77-5

• 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)-4-[Cyano-methyl-(5-pyridin-4-yl-furan-2-yl)-methyl]-piperazine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide
• CAS: 342600-77-5
• 化学式: C₁₉H₂₀F₃N₅O₂
• 分子量: 407.395
• InChiKey: UGMWJLLJSTZDGX-PIVQAISJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  94.19
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-4-[Cyano-methyl-(5-pyridin-4-yl-furan-2-yl)-methyl]-piperazine-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide 在 lithium hydroxide 、 四丁基氟化铵 、 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 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 (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：

  1-(5-pyridin-4-yl-furan-2-yl)-ethanone 在 tris(dibenzylideneacetone)dipalladium (0) 、 硫代水杨酸 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-4-[Cyano-methyl-(5-pyridin-4-yl-furan-2-yl)-methyl]-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