1-(4-cyanobenzyl)piperidine-4-carboxamide | 945298-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(4-cyanobenzyl)piperidine-4-carboxamide
• 英文别名: 1-[(4-cyanophenyl)methyl]piperidine-4-carboxamide
• CAS: 945298-47-5
• 化学式: C₁₄H₁₇N₃O
• mdl: MFCD09455284
• 分子量: 243.308
• InChiKey: CYLJLXZDKVEGCU-UHFFFAOYSA-N

物化性质

• 沸点：
  463.5±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-cyanobenzyl)piperidine-4-carboxamide 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Benzylpiperidine-Linked Diarylthiazoles as Potential Anti-Alzheimer’s Agents: Synthesis and Biological Evaluation

  摘要：

  A novel series of hybrid molecules were designed and synthesized by fusing the pharmacophoric features of cholinesterase inhibitor donepezil and diarylthiazole as potential multitarget-directed ligands for the treatment of Alzheimer's disease (AD). The compounds showed significant in vitro anticholinesterase (anti-ChE) activity, the most potent compound (44) among them showing the highest activity (IC50 value of 0.30 +/- 0.01 mu M) for AChE and (1.84 +/- 0.03 mu M) for BuChE. Compound 44 showed mixed inhibition of AChE in the enzyme kinetic studies. Some compounds exhibited moderate to high inhibition of AChE-induced A beta(1-42) aggregation and noticeable in vitro antioxidant and antiapoptotic properties. Compound 44 showed significant in vivo anti-ChE and antioxidant activities. Furthermore, compound 44 demonstrated in vivo neuroprotection by decreasing A beta(1-42)-induced toxicity by attenuating abnormal levels of A beta(1-42), p-Tau, cleaved caspase-3, and cleaved PARP proteins. Compound 44 exhibited good oral absorption and was well tolerated up to 2000 mg/kg, po, dose without showing toxic effects.

  DOI：

  10.1021/acs.jmedchem.6b00426
• 作为产物：
  描述：

  哌啶-4-甲酰胺 、 对氰基溴化苄 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以85%的产率得到1-(4-cyanobenzyl)piperidine-4-carboxamide
  参考文献：
  名称：

  Benzylpiperidine-Linked Diarylthiazoles as Potential Anti-Alzheimer’s Agents: Synthesis and Biological Evaluation

  摘要：

  A novel series of hybrid molecules were designed and synthesized by fusing the pharmacophoric features of cholinesterase inhibitor donepezil and diarylthiazole as potential multitarget-directed ligands for the treatment of Alzheimer's disease (AD). The compounds showed significant in vitro anticholinesterase (anti-ChE) activity, the most potent compound (44) among them showing the highest activity (IC50 value of 0.30 +/- 0.01 mu M) for AChE and (1.84 +/- 0.03 mu M) for BuChE. Compound 44 showed mixed inhibition of AChE in the enzyme kinetic studies. Some compounds exhibited moderate to high inhibition of AChE-induced A beta(1-42) aggregation and noticeable in vitro antioxidant and antiapoptotic properties. Compound 44 showed significant in vivo anti-ChE and antioxidant activities. Furthermore, compound 44 demonstrated in vivo neuroprotection by decreasing A beta(1-42)-induced toxicity by attenuating abnormal levels of A beta(1-42), p-Tau, cleaved caspase-3, and cleaved PARP proteins. Compound 44 exhibited good oral absorption and was well tolerated up to 2000 mg/kg, po, dose without showing toxic effects.

  DOI：

  10.1021/acs.jmedchem.6b00426

文献信息

• Substituted Pyridine, Pyridazine, Pyrazine And Pyrimidine Compounds And Methods For Using The Same
  申请人：Goff Dane

  公开号：US20120028954A1

  公开（公告）日：2012-02-02

  Disclosed are substituted pyridine compounds as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure wherein E, J, T, the ring system denoted by “B”, T, R 3 , R 4 , w and x are as described herein. In certain embodiments, a compound disclosed herein activates the AMPK pathway, and can be used to treat metabolism-related disorders and conditions.

  本发明涉及取代吡啶化合物以及其药物组合物和使用方法。其中一种实施例是一种具有以下结构的化合物，其中E、J、T、用“B”表示的环系统、T、R3、R4、w和x如本文所述。在某些实施例中，本文所披露的化合物可以激活AMPK途径，并可用于治疗与新陈代谢有关的疾病和症状。
• AMPK-ACTIVATING HETEROCYCLIC COMPOUNDS AND METHODS FOR USING THE SAME
  申请人：RIGEL PHARMACEUTICALS, INC.

  公开号：US20130267701A1

  公开（公告）日：2013-10-10

  Disclosed are substituted pyridine compounds as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure wherein E, J, T, the ring system denoted by “B”, T, R 3 , R 4 , w and x are as described herein. In certain embodiments, a compound disclosed herein activates the AMPK pathway, and can be used to treat metabolism-related disorders and conditions.

  本发明涉及取代吡啶化合物、药物组合物和使用方法。其中一种实施方式是具有以下结构的化合物，其中E、J、T、由“B”表示的环系统、T、R3、R4、w和x如所述。在某些实施方式中，本文所披露的化合物可以激活AMPK通路，并可用于治疗与代谢有关的疾病和病症。
• Substituted pyridine, pyridazine, pyrazine and pyrimidine compounds and methods for using the same
  申请人：Goff Dane

  公开号：US08791136B2

  公开（公告）日：2014-07-29

  Disclosed are substituted pyridine compounds as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure wherein E, J, T, the ring system denoted by “B”, T, R3, R4, w and x are as described herein. In certain embodiments, a compound disclosed herein activates the AMPK pathway, and can be used to treat metabolism-related disorders and conditions.

  本发明涉及取代吡啶化合物、药物组合物和使用方法。其中一种实施例为具有以下结构的化合物，其中E、J、T、用“B”表示的环系统、T、R3、R4、w和x如本文所述。在某些实施例中，本文所披露的化合物可以激活AMPK途径，并可用于治疗与代谢有关的疾病和病况。
• AMPK-activating heterocyclic compounds and methods for using the same
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：US08809370B2

  公开（公告）日：2014-08-19

  Disclosed are substituted pyridine compounds as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure wherein E, J, T, the ring system denoted by “B”, T, R3, R4, w and x are as described herein. In certain embodiments, a compound disclosed herein activates the AMPK pathway, and can be used to treat metabolism-related disorders and conditions.

  本发明涉及取代的吡啶化合物，以及其制药组合物和使用方法。其中一种实施例是具有以下结构的化合物，其中E，J，T，被标记为“B”的环系统，T，R3，R4，w和x如本文所述。在某些实施例中，本文所披露的化合物可以激活AMPK通路，并可用于治疗与代谢有关的疾病和病况。
• AMPK—activating heterocyclic compounds and methods for using the same
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：US09266856B2

  公开（公告）日：2016-02-23

  Disclosed are substituted pyridine compounds as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure wherein E, J, T, the ring system denoted by “B”, T, R3, R4, w and x are as described herein. In certain embodiments, a compound disclosed herein activates the AMPK pathway, and can be used to treat metabolism-related disorders and conditions.

  本发明涉及取代吡啶化合物，以及其制备的药物组合物和使用方法。其中一种实施例是具有以下结构的化合物，其中E、J、T、表示为“B”的环系统、R3、R4、w和x如本文所述。在某些实施例中，本文所披露的化合物可以激活AMPK通路，并可用于治疗代谢相关的疾病和病状。