tert-butyl (1R,5S)-3-(aminomethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate | 273207-53-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: tert-butyl (1R,5S)-3-(aminomethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate
• 英文别名: tert-butyl (endo)-3-aminomethyl-8-azabicyclo[3.2.1]octane-8-carboxylate
• CAS: 273207-53-7
• 化学式: C₁₃H₂₄N₂O₂
• 分子量: 240.346
• InChiKey: JYURWVQSNWVJSV-RTCCRHLQSA-N

物化性质

• 沸点：
  333.9±15.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,5S)-3-(aminomethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 水 、 异丙醇 、 正丁醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2,4-disubstituted quinazoline analogues as GPR119 agonists

  摘要：

  GPR119 agonist has emerged as a promising target for the treatment of type 2 diabetes. A series of novel 2,4-disubstituted quinazoline analogues was prepared and evaluated their agonistic activity against human GPR119. The analogues bearing azabicyclic amine substituents (12a, 12c and 12g) exhibited better EC50 values than that of OEA though they appeared to be partial agonists. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.013
• 作为产物：
  描述：

  methyl [(endo)-8-tert-butoxycarbonyl-8-azabicyclo[3.2.1]octan-3-yl]acetate 在 盐酸 、 叠氮磷酸二苯酯 、 5%-palladium/activated carbon 、 氢气 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 tert-butyl (1R,5S)-3-(aminomethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate
  参考文献：
  名称：

  SUBSTITUTED TROPANE DERIVATIVES

  摘要：

  公开号：

  EP3150598B1

文献信息

• Optimisation of novel 4, 8-disubstituted dihydropyrimido[5,4-<i>b</i>][1,4]oxazine derivatives as potent GPR 119 agonists
  作者：Yuanying Fang、Shaokun Zhang、Min Li、Lijuan Xiong、Liangxing Tu、Saisai Xie、Yi Jin、Yanhua Liu、Zunhua Yang、Ronghua Liu

  DOI：10.1080/14756366.2019.1681988

  日期：2020.1.1

  GPR119 is a promising target for discovery of anti-type 2 diabetes mellitus agents. We described the optimisation of a novel series of pyrimido[5,4-b][1,4]oxazine derivatives as GPR119 agonists. Most designed compounds exhibited good agonistic activities. Among them, compound 10 and 15 demonstrated the potent EC50 values (13 and 12 nM, respectively) and strong inherent activities. Moreover, significant

  GPR119是发现抗2型糖尿病药物的有希望的靶标。我们描述了作为GPR119激动剂的一系列新的嘧啶并[5,4-b] [1,4]恶嗪衍生物的优化。大多数设计的化合物表现出良好的激动活性。其中，化合物10和15表现出有效的EC50值（分别为13和12 nM）和强大的固有活性。此外，通过以30 mg / kg的剂量降低血糖AUC0-2h，观察到化合物15的显着降血糖作用，这比维格列汀强（降幅23.4％对降幅17.9％）。
• Synthesis and biological evaluation of 5-nitropyrimidine analogs with azabicyclic substituents as GPR119 agonists
  作者：Zunhua Yang、Yuanying Fang、Tuan-Anh N. Pham、Jongkook Lee、Haeil Park

  DOI：10.1016/j.bmcl.2012.12.011

  日期：2013.3

  5-Nitropyrimidine analogs substituted with conformationally restricted azabicyclic amines and alcohols were prepared and evaluated their agonistic activity against human GPR119. The analogs bearing endo-azabicyclic amines and alcohols (7, 8, 11, and 12) exhibited full agonistic activities while the analogs with exo-azabicyclic amines and alcohols were proved as partial agonists (9, 10, 13, and 14) regardless of their EC50 values. 5-Nitropyrimidine analogs with (2-fluoro-4-methylsulfonyl)phenylamino group (8, 10, 12, 14) showed more potent GPR119 activation activities than the analogs without fluorine in all cases (7, 9, 11, 13). (c) 2012 Elsevier Ltd. All rights reserved.
• SUBSTITUTED TROPANE DERIVATIVES
  申请人：TOA Eiyo Ltd.

  公开号：EP3150598B1

  公开（公告）日：2019-02-13
• Synthesis and biological evaluation of novel 2,4-disubstituted quinazoline analogues as GPR119 agonists
  作者：Tuan-Anh N. Pham、Zunhua Yang、Yuanying Fang、Jun Luo、Jongkook Lee、Haeil Park

  DOI：10.1016/j.bmc.2012.12.013

  日期：2013.3

  GPR119 agonist has emerged as a promising target for the treatment of type 2 diabetes. A series of novel 2,4-disubstituted quinazoline analogues was prepared and evaluated their agonistic activity against human GPR119. The analogues bearing azabicyclic amine substituents (12a, 12c and 12g) exhibited better EC50 values than that of OEA though they appeared to be partial agonists. (C) 2012 Elsevier Ltd. All rights reserved.