(2S)-cyclohexyl(hept-6-en-1-ylamino)ethanoic acid | 1000064-14-1

• 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)-cyclohexyl(hept-6-en-1-ylamino)ethanoic acid
• 英文别名: (2S)-Cyclohexyl(hept-6-en-1-ylamino)acetic acid；(2S)-2-cyclohexyl-2-(hept-6-enylamino)acetic acid
• CAS: 1000064-14-1
• 化学式: C₁₅H₂₇NO₂
• 分子量: 253.385
• InChiKey: QCHALCKDNJBKTB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：

  (2S)-cyclohexyl(hept-6-en-1-ylamino)ethanoic acid 、 methyl (2S,4R)-4-(7-ethenyl-6-methoxyisoquinolin-1-yl)oxypyrrolidine-2-carboxylate 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到methyl (4R)-1-[(2S)-2-cyclohexyl-2-(hept-6-en-1-ylamino)acetyl]-4-[(6-methoxy-7-vinylisoquinolin-1-yl)oxy]-L-prolinate
  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
• 作为产物：
  描述：

  在 甲醇 、 lithium hydroxide monohydrate 、 水 作用下， 反应 22.0h， 生成 (2S)-cyclohexyl(hept-6-en-1-ylamino)ethanoic acid
  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

• Macrocyclic Compounds as Antiviral Agents
  申请人：Crescenzi Benedetta

  公开号：US20090312241A1

  公开（公告）日：2009-12-17

  The present invention relates to macrocyclic compounds of formula (I): wherein W, n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R a , M, Z and ring B are defined herein, and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising them, and their use for the treatment or prevention of infection by hepatitis C virus.

  本发明涉及式（I）的大环化合物：其中W、n、m、R1、R2、R3、R4、R5、Ra、M、Z和环B在此处定义，并其药用盐，包含它们的药物组合物，以及它们用于治疗或预防丙型肝炎病毒感染的用途。
• MACROCYCLIC COMPOUNDS AS ANTIVIRAL AGENTS
  申请人：Istituto di Ricerche di Biologia Molecolare P. Angeletti S.p.A.

  公开号：EP2041159B1

  公开（公告）日：2011-09-28
• US8314062B2
  申请人：——

  公开号：US8314062B2

  公开（公告）日：2012-11-20
• 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.