Benzyl 1-aminocyclohexane-1-carboxylate;hydrochloride | 101114-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzyl 1-aminocyclohexane-1-carboxylate;hydrochloride
• CAS: 101114-29-8
• 化学式: C₁₄H₁₉NO₂*ClH
• 分子量: 269.771
• InChiKey: VHAHGTVJRPFLLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzyl 1-aminocyclohexane-1-carboxylate;hydrochloride 、 4-三氟甲氧基苯甲酸 在 二乙基异丙基胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Benzyl 1-[[4-(trifluoromethoxy)benzoyl]amino]cyclohexane-1-carboxylate
  参考文献：
  名称：

  Keto-1,3,4-oxadiazoles as cathepsin K inhibitors

  摘要：

  We have prepared a series of cathepsin K inhibitors bearing the keto-1,3,4-oxadiazole warhead capable of forming a hemithioketal complex with the target enzyme. By modifying binding moieties at the P-1, P-2, and prime side positions of the inhibitors, we have achieved selectivity over cathepsins B, L, and S, and have achieved sub-nanomolar potency against cathepsin K. This series thus represents a promising chemotype that could be used in diseases implicated by imbalances in cathepsin K activity such as osteoporosis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.001
• 作为产物：
  描述：

  benzyl 1-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 Benzyl 1-aminocyclohexane-1-carboxylate;hydrochloride
  参考文献：
  名称：

  Keto-1,3,4-oxadiazoles as cathepsin K inhibitors

  摘要：

  We have prepared a series of cathepsin K inhibitors bearing the keto-1,3,4-oxadiazole warhead capable of forming a hemithioketal complex with the target enzyme. By modifying binding moieties at the P-1, P-2, and prime side positions of the inhibitors, we have achieved selectivity over cathepsins B, L, and S, and have achieved sub-nanomolar potency against cathepsin K. This series thus represents a promising chemotype that could be used in diseases implicated by imbalances in cathepsin K activity such as osteoporosis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.001

文献信息

• [EN] CYSTEINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA CYSTEINE PROTEASE
  申请人：AXYS PHARM INC

  公开号：WO2002023784A2

  公开（公告）日：2002-03-21

  The present invention relates to compounds, compositions and methods for treating diseases associated with cysteine protease activity, particularly diseases associated with activity of cathepsins B, K, L or S.The present invention thus provides compounds of Formula (I): pharmaceutical compositions comprising compounds of Formula (I) and methods of treating diseases associated with cysteine protease activity using pharmaceutical compositions comprising compounds of Formula (I).
• Keto-1,3,4-oxadiazoles as cathepsin K inhibitors
  作者：James T. Palmer、Bernard L. Hirschbein、Harry Cheung、John McCarter、James W. Janc、Z. Walter Yu、Gregg Wesolowski

  DOI：10.1016/j.bmcl.2006.03.001

  日期：2006.6

  We have prepared a series of cathepsin K inhibitors bearing the keto-1,3,4-oxadiazole warhead capable of forming a hemithioketal complex with the target enzyme. By modifying binding moieties at the P-1, P-2, and prime side positions of the inhibitors, we have achieved selectivity over cathepsins B, L, and S, and have achieved sub-nanomolar potency against cathepsin K. This series thus represents a promising chemotype that could be used in diseases implicated by imbalances in cathepsin K activity such as osteoporosis. (c) 2006 Elsevier Ltd. All rights reserved.
• Toward the Back-Up of Boceprevir (SCH 503034): Discovery of New Extended P₄-Capped Ketoamide Inhibitors of Hepatitis C Virus NS3 Serine Protease with Improved Potency and Pharmacokinetic Profiles
  作者：Stéphane L. Bogen、Weidong Pan、Sumei Ruan、Latha G. Nair、Ashok Arasappan、Frank Bennett、Kevin X. Chen、Edwin Jao、Srikanth Venkatraman、Bancha Vibulbhan、Rong Liu、Kuo-Chi Cheng、Zhuyan Guo、Xiao Tong、Anil K. Saksena、Viyyoor Girijavallabhan、F. George Njoroge

  DOI：10.1021/jm801632a

  日期：2009.6.25

  Hepatitis C is the most prevalent liver disease. Viral hepatitis C (HCV), a small (+)-RNA virus, infects chronically an estimated 300 million people worldwide. Results of Phase I clinical studies with our first generation HCV inhibitor Boceprevir, SCH 503034 (1), presented at the 56th Annual Meeting of the American Association for the Study of Liver Diseases (AASLD) were encouraging, and thus, additional human clinical studies are underway. In view of the positive data from our first generation compound, further work aimed at optimizing its overall profile was undertaken. Herein, we report that extension of our earlier inhibitor to the P-4 pocket and optimization of the P-1' capping led to the discovery of new ketoamide inhibitors of the HCV NS3 serine protease with improved in vitro potency. In addition to being potent inhibitors of HCV subgenomic RNA replication, some of the new P-4-capped inhibitors were also found to have improved PK profile.