methyl (2S)-2-[[(2S,3S)-2-[(2-bromoacetyl)amino]-3-methylpentanoyl]amino]-3-phenylpropanoate | 215512-40-6

• 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: methyl (2S)-2-[[(2S,3S)-2-[(2-bromoacetyl)amino]-3-methylpentanoyl]amino]-3-phenylpropanoate
• CAS: 215512-40-6
• 化学式: C₁₈H₂₅BrN₂O₄
• 分子量: 413.311
• InChiKey: FGRSKWRPCBLUFE-NOLJZWGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(2S,3S)-2-[(2-bromoacetyl)amino]-3-methylpentanoyl]amino]-3-phenylpropanoate 在 碳酸氢钠 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-Phe-N(OBn)Gly-Ile-Phe-OMe
  参考文献：
  名称：

  Synthesis and activity of HIV protease inhibitors

  摘要：

  We report here the synthesis and activity of HIV protease inhibitors. Ln the first stage hydrophobic compounds incorporating a 'carba' bond surrogate or a beta-homologated residue were synthesized. Secondly, we synthesized cyclic compounds in which we incorporated 2-quinoline carboxylic acid in the P3 position and the amino-hydroxyindane moiety in the P'3. The last part of this work was dedicated to a structure/activity study of a peptide substrate. These modifications allowed us to work up the synthesis of new pseudopeptide bonds: amino-amide and hydroxy-amide, Compounds with activity in the micromolar range were actually a starting point for the synthesis of new protease inhibitors. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80043-3
• 作为产物：
  描述：

  BOC-L-异亮氨酸 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 methyl (2S)-2-[[(2S,3S)-2-[(2-bromoacetyl)amino]-3-methylpentanoyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis and activity of HIV protease inhibitors

  摘要：

  We report here the synthesis and activity of HIV protease inhibitors. Ln the first stage hydrophobic compounds incorporating a 'carba' bond surrogate or a beta-homologated residue were synthesized. Secondly, we synthesized cyclic compounds in which we incorporated 2-quinoline carboxylic acid in the P3 position and the amino-hydroxyindane moiety in the P'3. The last part of this work was dedicated to a structure/activity study of a peptide substrate. These modifications allowed us to work up the synthesis of new pseudopeptide bonds: amino-amide and hydroxy-amide, Compounds with activity in the micromolar range were actually a starting point for the synthesis of new protease inhibitors. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80043-3

文献信息

• Synthesis and activity of HIV protease inhibitors
  作者：Patrick Garrouste、Macek Pawlowski、Thierry Tonnaire、Sames Sicsic、Pascal Dumy、Eve de Rosny、Michèle Reboud-Ravaux、Pierre Fulcrand、Jean Martinez

  DOI：10.1016/s0223-5234(98)80043-3

  日期：1998.6

  We report here the synthesis and activity of HIV protease inhibitors. Ln the first stage hydrophobic compounds incorporating a 'carba' bond surrogate or a beta-homologated residue were synthesized. Secondly, we synthesized cyclic compounds in which we incorporated 2-quinoline carboxylic acid in the P3 position and the amino-hydroxyindane moiety in the P'3. The last part of this work was dedicated to a structure/activity study of a peptide substrate. These modifications allowed us to work up the synthesis of new pseudopeptide bonds: amino-amide and hydroxy-amide, Compounds with activity in the micromolar range were actually a starting point for the synthesis of new protease inhibitors. (C) Elsevier, Paris.