2-[(S)-4-Allyl-3-(2,2,2-trifluoro-ethylcarbamoyl)-piperazin-1-yl]-2-methyl-propionic acid | 600739-77-3

• 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: 2-[(S)-4-Allyl-3-(2,2,2-trifluoro-ethylcarbamoyl)-piperazin-1-yl]-2-methyl-propionic acid
• 英文别名: 2-methyl-2-[(3S)-4-prop-2-enyl-3-(2,2,2-trifluoroethylcarbamoyl)piperazin-1-yl]propanoic acid
• CAS: 600739-77-3
• 化学式: C₁₄H₂₂F₃N₃O₃
• 分子量: 337.342
• InChiKey: YHVOSPFPHGRSMU-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(S)-4-Allyl-3-(2,2,2-trifluoro-ethylcarbamoyl)-piperazin-1-yl]-2-methyl-propionic acid 在 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 硫酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 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-[5-(5-methoxy-3-pyridinyl)-2-oxazolyl]-1-methylethyl]-α-(phenylmethyl)-2-[[(2,2,2-trifluoroethyl)amino]carbonyl]-1-piperazinepentanamide
  参考文献：
  名称：

  The design, synthesis and evaluation of novel HIV-1 protease inhibitors with high potency against PI-resistant viral strains

  摘要：

  Replacement of the pyridylmethyl moiety in indinavir with a pyridyl oxazole yielded HIV-1 protease inhibitors (PI) with greatly improved potency against PI-resistant HIV-1 strains. A meta-methoxy group on the pyridyl ring and a gem-dimethyl methyl linkage afforded compound 10 with notable in vitro antiviral activity against HIV-1 viral strains with reduced susceptibility to the clinically available PIs. Compound 10 also demonstrated favorable in vivo pharmacokinetics in animal models. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00474-8
• 作为产物：
  描述：

  (S)-4-Allyl-3-(2,2,2-trifluoro-ethylcarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester 在 TEA 、 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-[(S)-4-Allyl-3-(2,2,2-trifluoro-ethylcarbamoyl)-piperazin-1-yl]-2-methyl-propionic acid
  参考文献：
  名称：

  The design, synthesis and evaluation of novel HIV-1 protease inhibitors with high potency against PI-resistant viral strains

  摘要：

  Replacement of the pyridylmethyl moiety in indinavir with a pyridyl oxazole yielded HIV-1 protease inhibitors (PI) with greatly improved potency against PI-resistant HIV-1 strains. A meta-methoxy group on the pyridyl ring and a gem-dimethyl methyl linkage afforded compound 10 with notable in vitro antiviral activity against HIV-1 viral strains with reduced susceptibility to the clinically available PIs. Compound 10 also demonstrated favorable in vivo pharmacokinetics in animal models. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00474-8

文献信息

• The design, synthesis and evaluation of novel HIV-1 protease inhibitors with high potency against PI-resistant viral strains
  作者：Fengqi Zhang、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)00474-8

  日期：2003.8

  Replacement of the pyridylmethyl moiety in indinavir with a pyridyl oxazole yielded HIV-1 protease inhibitors (PI) with greatly improved potency against PI-resistant HIV-1 strains. A meta-methoxy group on the pyridyl ring and a gem-dimethyl methyl linkage afforded compound 10 with notable in vitro antiviral activity against HIV-1 viral strains with reduced susceptibility to the clinically available PIs. Compound 10 also demonstrated favorable in vivo pharmacokinetics in animal models. (C) 2003 Elsevier Ltd. All rights reserved.