(2S)-cyclopentyl[oct-7-en-2-ylamino]ethanoic acid | 1179842-27-3

• 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: (2S)-cyclopentyl[oct-7-en-2-ylamino]ethanoic acid
• 英文别名: (2S)-2-cyclopentyl-2-(oct-7-en-2-ylamino)acetic acid
• CAS: 1179842-27-3
• 化学式: C₁₅H₂₇NO₂
• 分子量: 253.385
• InChiKey: SNPIAOGLXJOSHS-PYMCNQPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Vinyl-1,3-dihydro-isoindole-2-carboxylic acid 5-methoxycarbonyl-pyrrolidin-3-yl ester 、 (2S)-cyclopentyl[oct-7-en-2-ylamino]ethanoic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,5S)-1-{(2S)-2-cyclopentyl-2-[(2R)-oct-7-en-2-ylamino]acetyl}-5-(methoxycarbonyl)pyrrolidin-3-yl 4-ethenyl-1,3-dihydro-2H-isoindole-2-carboxylate 、 (3R,5S)-1-{(2R)-2-cyclopentyl-2-[(2R)-oct-7-en-2-ylamino]acetyl}-5-(methoxycarbonyl)pyrrolidin-3-yl 4-ethenyl-1,3-dihydro-2H-isoindole-2-carboxylate
  参考文献：
  名称：

  Inhibitors of the Hepatitis C Virus NS3 Protease with Basic Amine Functionality at the P3-Amino Acid N-Terminus: Discovery and Optimization of a New Series of P2−P4 Macrocycles

  摘要：

  In a follow-Lip to our recent disclosure of P2-P4 macrocyclic inhibitors of the hepatitis C virus (HCV) NS3 protease (e.g., 1, Chart 1), we report a new but related compound series featuring a basic amine at the N-terminus of the P3-amino acid residue. Replacement of the electroneutral P3-amino acid capping group (which is a feature of almost all tripeptide-like inhibitors of NS3 reported to date) with a basic group is not only tolerated but can result in advantageous cell based potency. Optimization of this new class of P3-amine based inhibitors gave compounds such as 25 and 26 that combine excellent cell based activity with pharmacokinetic properties that are attractive for an antiviral targeting HCV.

  DOI：

  10.1021/jm900372w

文献信息

• Inhibitors of the Hepatitis C Virus NS3 Protease with Basic Amine Functionality at the P3-Amino Acid N-Terminus: Discovery and Optimization of a New Series of P2−P4 Macrocycles
  作者：Steven Harper、Marco Ferrara、Benedetta Crescenzi、Marco Pompei、Maria Cecilia Palumbi、Jillian M. DiMuzio、Monica Donghi、Fabrizio Fiore、Uwe Koch、Nigel J. Liverton、Silvia Pesci、Alessia Petrocchi、Michael Rowley、Vincenzo Summa、Cristina Gardelli

  DOI：10.1021/jm900372w

  日期：2009.8.13

  In a follow-Lip to our recent disclosure of P2-P4 macrocyclic inhibitors of the hepatitis C virus (HCV) NS3 protease (e.g., 1, Chart 1), we report a new but related compound series featuring a basic amine at the N-terminus of the P3-amino acid residue. Replacement of the electroneutral P3-amino acid capping group (which is a feature of almost all tripeptide-like inhibitors of NS3 reported to date) with a basic group is not only tolerated but can result in advantageous cell based potency. Optimization of this new class of P3-amine based inhibitors gave compounds such as 25 and 26 that combine excellent cell based activity with pharmacokinetic properties that are attractive for an antiviral targeting HCV.