(3S)-3-[(2S)-2-[(6-chloro-1,3-benzoxazol-2-yl)amino]-3-cyclohexylpropanamido]-4-(5-fluoro-2,3-dihydro-1H-indol-1-yl)butanoic acid | 819075-95-1

• 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: (3S)-3-[(2S)-2-[(6-chloro-1,3-benzoxazol-2-yl)amino]-3-cyclohexylpropanamido]-4-(5-fluoro-2,3-dihydro-1H-indol-1-yl)butanoic acid
• 英文别名: (3S)-3-[[(2S)-2-[(6-chloro-1,3-benzoxazol-2-yl)amino]-3-cyclohexylpropanoyl]amino]-4-(5-fluoro-2,3-dihydroindol-1-yl)butanoic acid
• CAS: 819075-95-1
• 化学式: C₂₈H₃₂ClFN₄O₄
• 分子量: 543.038
• InChiKey: ICWNTBUEKRQPME-GMAHTHKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S)-3-[(2S)-2-[(6-chloro-1,3-benzoxazol-2-yl)amino]-3-cyclohexylpropanamido]-4-(5-fluoro-2,3-dihydro-1H-indol-1-yl)butanoic acid 、 乙醇 在 对甲苯磺酸 、 原甲酸三乙酯 作用下， 生成 ethyl (3S)-3-[(2S)-2-[(6-chloro-1,3-benzoxazol-2-yl)amino]-3-cyclohexylpropanamido]-4-(5-fluoro-2,3-dihydro-1H-indol-1-yl)butanoate
  参考文献：
  名称：

  Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3

  摘要：

  A series of N-alpha-2-benzoxazolyl-alpha-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure-activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound 3 bound to the active site of cathepsin S is also reported. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.095
• 作为产物：
  描述：

  2-氨基-5-氯苯酚 在 lithium hydroxide 、 五氯化磷 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S)-3-[(2S)-2-[(6-chloro-1,3-benzoxazol-2-yl)amino]-3-cyclohexylpropanamido]-4-(5-fluoro-2,3-dihydro-1H-indol-1-yl)butanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3

  摘要：

  A series of N-alpha-2-benzoxazolyl-alpha-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure-activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound 3 bound to the active site of cathepsin S is also reported. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.095

文献信息

• US7307095B2
  申请人：——

  公开号：US7307095B2

  公开（公告）日：2007-12-11
• Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3
  作者：David C. Tully、Hong Liu、Phil B. Alper、Arnab K. Chatterjee、Robert Epple、Michael J. Roberts、Jennifer A. Williams、KhanhLinh T. Nguyen、David H. Woodmansee、Christine Tumanut、Jun Li、Glen Spraggon、Jonathan Chang、Tove Tuntland、Jennifer L. Harris、Donald S. Karanewsky

  DOI：10.1016/j.bmcl.2005.12.095

  日期：2006.4

  A series of N-alpha-2-benzoxazolyl-alpha-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure-activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound 3 bound to the active site of cathepsin S is also reported. (C) 2006 Elsevier Ltd. All rights reserved.