4-methoxy-N-(pyridin-4-yl)benzamide | 14547-75-2

• 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: 4-methoxy-N-(pyridin-4-yl)benzamide
• 英文别名: 4-<4-Methoxy-benzoylamino>pyridin；4-methoxy-N-pyridin-4-ylbenzamide
• CAS: 14547-75-2
• 化学式: C₁₃H₁₂N₂O₂
• mdl: MFCD00750996
• 分子量: 228.25
• InChiKey: PJCYIPIOMMKQMC-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  320.0±22.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(pyridin-4-yl)benzamide 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  通过轻松修饰C，N-二齿螯合亚吡啶基亚酰胺配体提高铱（III）配合物的催化活性。

  摘要：

  在五甲基环戊二烯基（Cp *）铱中心，将一组由于明显的两性离子和中性二烯型共振结构而具有可变的给体性质的芳基取代的吡啶基亚酰胺（PYA）配体用作电子柔性配体。这种类型的配体的直接合成使得可以容易地在C，N-二齿螯合PYA的苯环的不同位置引入供体取代基，例如甲氧基。这些修饰大大增强了配位铱中心对羰基和亚胺的需氧转移催化氢化以及苯乙炔的氢化硅烷化的催化活性。而且，这些PYA铱络合物催化醛的无碱转移氢化，并且在较小程度上也催化酮。

  DOI：

  10.1021/acs.inorgchem.7b01654
• 作为产物：
  描述：

  大茴香酸 在 草酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-methoxy-N-(pyridin-4-yl)benzamide
  参考文献：
  名称：

  Discovery of methoxy-naphthyl linked N-(1-benzylpiperidine) benzamide as a blood-brain permeable dual inhibitor of acetylcholinesterase and butyrylcholinesterase

  摘要：

  The cholinesterase enzymes play a vital role in maintaining balanced levels of the neurotransmitter acetylcholine in the central nervous system. However, the overexpression of these enzymes results in hampered neurotransmission. Both the major forms of cholinesterase enzymes viz. acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) play a crucial role in blocking neurotransmission; therefore, in recent years, a strategy of dual cholinesterase inhibition is being explored. Herein, we developed an energy-optimized e-pharmacophore hypothesis AHHPRR from AChE-donepezil complex and screened a set of 15 scaffolds that were designed imaginarily. The ligand with N-(1-benzylpyridinium) benzamide framework has shown the highest fitness and volume score, which was chosen for synthesis and validation. A series of pyridinium benzamides were synthesized and screened for cholinesterase inhibition that led to the identification of 7b, a naphthalene containing N-(1-benzylpiperidine) benzamide as a potent dual AChE and BChE inhibitor with IC₅₀ values of 0.176, and 0.47 μM, respectively. The kinetic study indicated that 7b inhibits AChE in a non-competitive manner with Ki value of 0.21 μM, and BChE in a mixed-fashion with Ki of 0.15 μM. The observed mode of inhibition was corroborated with molecular docking studies. The MD simulation studies pointed out that both AChE and BChE undergo low conformational changes in complex with 7b. The benzamide 7b displayed high BBB permeability in PAMPA assay, which indicates its potential for further exploration in preclinical studies for Alzheimer's disease.

  DOI：

  10.1016/j.ejmech.2020.112761

文献信息

• Heteroaromatic quinoline compounds
  申请人：Verhoest R. Patrick

  公开号：US20060154931A1

  公开（公告）日：2006-07-13

  The invention pertains to heteroaromatic compounds that serve as effective phosphodiesterase (PDE) inhibitors. In particular, the invention relates to said compounds which are selective inhibitors of PDE10. The invention also relates to intermediates for preparation of said compounds; pharmaceutical compositions comprising said compounds; and the use of said compounds in a method for treating certain central nervous system (CNS) or other disorders.

  该发明涉及异芳香化合物，其作为有效的磷酸二酯酶（PDE）抑制剂。具体而言，该发明涉及选择性抑制PDE10的这些化合物。该发明还涉及用于制备这些化合物的中间体；包含这些化合物的药物组合物；以及利用这些化合物治疗某些中枢神经系统（CNS）或其他疾病的方法。
• BICYCLIC HETEROARYL COMPOUNDS AS PDE10 INHIBITORS
  申请人：Verhoest R, Patrick

  公开号：US20070155779A1

  公开（公告）日：2007-07-05

  The invention pertains to bicyclic heteroaryl compounds that serve as effective phosphodiesterase (PDE) inhibitors The invention also relates to compounds which are selective inhibitors of PDE-10. The invention further relates to intermediates for preparation of such compounds; pharmaceutical compositions comprising such compounds; and the use of such compounds in methods for treating certain central nervous system (CNS) or other disorders. The invention relates also to methods for treating neurodegenerative and psychiatric disorders, for example psychosis and disorders comprising deficient cognition as a symptom.

  这项发明涉及用作有效磷酸二酯酶（PDE）抑制剂的双环杂环芳基化合物。该发明还涉及选择性抑制PDE-10的化合物。此外，该发明还涉及制备这种化合物的中间体；包含这种化合物的药物组合物；以及将这种化合物用于治疗某些中枢神经系统（CNS）或其他疾病的方法。该发明还涉及治疗神经退行性和精神障碍的方法，例如精神病和包括认知缺陷作为症状的疾病。
• HETEROAROMATIC QUINOLINE COMPOUNDS
  申请人：Verhoest Patrick R.

  公开号：US20080214607A1

  公开（公告）日：2008-09-04

  The invention pertains to heteroaromatic compounds that serve as effective phosphodiesterase (PDE) inhibitors. In particular, the invention relates to said compounds which are selective inhibitors of PDE10. The invention also relates to intermediates for preparation of said compounds; pharmaceutical compositions comprising said compounds; and the use of said compounds in a method for treating certain central nervous system (CNS) or other disorders.

  该发明涉及异杂芳烃化合物，其作为有效的磷酸二酯酶（PDE）抑制剂。特别地，该发明涉及选择性抑制PDE10的该类化合物。该发明还涉及用于制备该类化合物的中间体；含有该类化合物的药物组合物；以及使用该类化合物治疗某些中枢神经系统（CNS）或其他疾病的方法。
• AKIMOTO, KODZI;SAKAKIBARA, VASEHJ;OSAVA, TATEHSI;KATO, SINITIRO
  作者：AKIMOTO, KODZI、SAKAKIBARA, VASEHJ、OSAVA, TATEHSI、KATO, SINITIRO

  DOI：——

  日期：——
• HETEROAROMATIC QUINOLINE COMPOUNDS AND THEIR USE AS PDE10 INHIBITORS
  申请人：Pfizer Products Inc.

  公开号：EP1841757B1

  公开（公告）日：2010-06-30