(S)-5,5-Difluoro-3-[(S)-2-((S)-2-hydroxy-2-thiophen-2-yl-acetylamino)-4-methyl-pentanoylamino]-2-oxo-pentanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-5,5-Difluoro-3-[(S)-2-((S)-2-hydroxy-2-thiophen-2-yl-acetylamino)-4-methyl-pentanoylamino]-2-oxo-pentanoic acid
• 英文别名: (3S)-5,5-difluoro-3-[[(2S)-2-[[(2S)-2-hydroxy-2-thiophen-2-ylacetyl]amino]-4-methylpentanoyl]amino]-2-oxopentanoic acid
• 化学式: C₁₇H₂₂F₂N₂O₆S
• 分子量: 420.434
• InChiKey: QMDCNQALVITTQM-PKFCDNJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S)-2-amino-N-[1-cyano-5,5-difluoro-2-oxo-1-(triphenyl-lambda5-phosphanylidene)pentan-3-yl]-4-methylpentanamide 在 sodium hydroxide 、 1-羟基苯并三唑 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-5,5-Difluoro-3-[(S)-2-((S)-2-hydroxy-2-thiophen-2-yl-acetylamino)-4-methyl-pentanoylamino]-2-oxo-pentanoic acid
  参考文献：
  名称：

  Capped dipeptide α-Ketoacid inhibitors of the HCV NS3 protease

  摘要：

  The N-terminal aminoacid of alpha-ketotripeptide inhibitors of the hepatitis C virus NS3 protease can be replaced with an alpha-hydroxy acid, leading to capped dipeptide inhibitors such as 20 with an IC50 value of 3.0 muM. The importance of the lipophilic side chain interactions at S3 of the protease and the requirement of the capping residue with R configuration have been explained by molecular modeling studies. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00691-1

文献信息

• Capped dipeptide α-Ketoacid inhibitors of the HCV NS3 protease
  作者：Emanuela Nizi、Uwe Koch、Simona Ponzi、Victor G Matassa、Cristina Gardelli

  DOI：10.1016/s0960-894x(02)00691-1

  日期：2002.11

  The N-terminal aminoacid of alpha-ketotripeptide inhibitors of the hepatitis C virus NS3 protease can be replaced with an alpha-hydroxy acid, leading to capped dipeptide inhibitors such as 20 with an IC50 value of 3.0 muM. The importance of the lipophilic side chain interactions at S3 of the protease and the requirement of the capping residue with R configuration have been explained by molecular modeling studies. (C) 2002 Elsevier Science Ltd. All rights reserved.