(S)-2-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 1234318-00-3

• 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: (S)-2-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[(5-tert-butyl-1,2-oxazol-3-yl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 1234318-00-3
• 化学式: C₁₇H₂₇N₃O₄
• 分子量: 337.419
• InChiKey: XUUCZASNEYQANB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 (S)-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide
  参考文献：
  名称：

  Selective CB2 receptor agonists. Part 2: Structure–activity relationship studies and optimization of proline-based compounds

  摘要：

  Through a ligand-based pharmacophore model (S)-proline based compounds were identified as potent cannabinoid receptor 2 (CB2) agonists with high selectivity over the cannabinoid receptor 1 (CB1). Structure-activity relationship investigations for this compound class lead to oxo-proline compounds 21 and 22 which combine an impressive CB1 selectivity profile with good pharmacokinetic properties. In a streptozotocin induced diabetic neuropathy model, 22 demonstrated a dose-dependent reversal of mechanical hyperalgesia. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.019
• 作为产物：
  描述：

  3-氨基-5-叔丁基异唑 、 BOC-L-脯氨酸 在 吡啶 、 三氯氧磷 作用下， 生成 (S)-2-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Selective CB2 receptor agonists. Part 2: Structure–activity relationship studies and optimization of proline-based compounds

  摘要：

  Through a ligand-based pharmacophore model (S)-proline based compounds were identified as potent cannabinoid receptor 2 (CB2) agonists with high selectivity over the cannabinoid receptor 1 (CB1). Structure-activity relationship investigations for this compound class lead to oxo-proline compounds 21 and 22 which combine an impressive CB1 selectivity profile with good pharmacokinetic properties. In a streptozotocin induced diabetic neuropathy model, 22 demonstrated a dose-dependent reversal of mechanical hyperalgesia. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.019

文献信息

• Pyrrolidine Compounds Which Modulate The CB2 Receptor
  申请人：Berry Angela

  公开号：US20120142677A1

  公开（公告）日：2012-06-07

  Compounds which modulate the CB2 receptor are disclosed. Compounds according to the invention bind to and are agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain. (I)

  本发明揭示了调节CB2受体的化合物。本发明的化合物结合并激动CB2受体，并且可用于治疗炎症。那些是激动剂的化合物还可用于治疗疼痛。 (I)
• [EN] PYRROLIDINE COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR<br/>[FR] COMPOSÉS PYRROLIDINES QUI MODULENT LE RÉCEPTEUR CB2
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010077836A3

  公开（公告）日：2010-09-16
• PYRROLIDINE COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2384320A2

  公开（公告）日：2011-11-09
• US8629157B2
  申请人：——

  公开号：US8629157B2

  公开（公告）日：2014-01-14