N-[(4-cyanophenyl)methyl]piperidine-4-carboxamide | 1105111-56-5

• 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: N-[(4-cyanophenyl)methyl]piperidine-4-carboxamide
• CAS: 1105111-56-5
• 化学式: C₁₄H₁₇N₃O
• 分子量: 243.308
• InChiKey: NSGRUXXVGCEYPI-UHFFFAOYSA-N

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：
  0.43
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(3-chloropropyl)aniline 、 N-[(4-cyanophenyl)methyl]piperidine-4-carboxamide 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 1-acetyl-N-(3-chlorophenyl)-N-(3-(4-(4-cyanobenzylcarbamoyl)piperidin-1-yl)propyl)piperidine-4-carboxamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel piperidine-4-carboxamide derivatives as potent CCR5 inhibitors

  摘要：

  Based on a putative 'Y shape' pharmacophore model of CCR5 inhibitors, a series of novel piperidine-4-carboxamide derivatives were designed and synthesized using a group-reverse strategy. Among synthesized target compounds, 16g (IC50 = 25.73 nM) and 16i (IC50 = 25.53 nM) showed equivalent inhibitory activity against CCR5 to that of the positive control maraviroc (IC50 = 25.43 nM) in calcium mobilization assay. Selected compounds were further tested for their antiviral activity in HIV-1 single cycle assay. Two compounds, 16g and 16i, displayed antiviral activity with IC50 values of 73.01 nM and 94.10 nM, respectively. Additionally, the pharmacokinetic properties and inhibitory potency against hERG of 16g were evaluated, providing a foundation for ongoing optimization. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.013
• 作为产物：
  描述：

  tert-butyl 4-(4-cyanobenzylcarbamoyl)piperidine-1-carboxylate 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 N-[(4-cyanophenyl)methyl]piperidine-4-carboxamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel piperidine-4-carboxamide derivatives as potent CCR5 inhibitors

  摘要：

  Based on a putative 'Y shape' pharmacophore model of CCR5 inhibitors, a series of novel piperidine-4-carboxamide derivatives were designed and synthesized using a group-reverse strategy. Among synthesized target compounds, 16g (IC50 = 25.73 nM) and 16i (IC50 = 25.53 nM) showed equivalent inhibitory activity against CCR5 to that of the positive control maraviroc (IC50 = 25.43 nM) in calcium mobilization assay. Selected compounds were further tested for their antiviral activity in HIV-1 single cycle assay. Two compounds, 16g and 16i, displayed antiviral activity with IC50 values of 73.01 nM and 94.10 nM, respectively. Additionally, the pharmacokinetic properties and inhibitory potency against hERG of 16g were evaluated, providing a foundation for ongoing optimization. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.013

文献信息

• [EN] 1-{2-[(DIPHENYL)AMINO]-ETHYL}-PIPERIDINE-4-CARBOXYLIC ACID BENZYLAMIDE DERIVATIVES AND RELATED COMPOUNDS AS CCR5 AGONISTS FOR THE TREATMENT OF IMMUNE AND INFLAMMATORY DISEASES<br/>[FR] DÉRIVÉS DE BENZYLAMIDE DE L'ACIDE 1-{2-[(DIPHÉNYL)AMINO]-ÉTHYL}-PIPÉRIDINE-4-CARBOXYLIQUE ET COMPOSÉS ASSOCIÉS COMME AGONISTES DE CCR5 POUR LE TRAITEMENT DE MALADIES IMMUNES ET INFLAMMATOIRES
  申请人：EUROSCREEN SA

  公开号：WO2009010480A1

  公开（公告）日：2009-01-22

  The present invention relates to pharmaceutically active piperidine derivatives and their use as agonists of CC chemokine receptor activity, more specifically of CCR5 activity. Chemokines are chemotactic cytokines which play an important role in immune and inflammatory responses.

  本发明涉及具有药理活性的哌啶衍生物，以及它们作为CC趋化因子受体活性激动剂的用途，更具体地是CCR5活性的激动剂。趋化因子是趋化细胞因子，在免疫和炎症反应中发挥重要作用。
• AMPK-ACTIVATING HETEROCYCLIC COMPOUNDS AND METHODS FOR USING THE SAME
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：EP2598483A1

  公开（公告）日：2013-06-05
• [EN] AMPK-ACTIVATING HETEROCYCLIC COMPOUNDS AND METHODS FOR USING THE SAME<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES D'ACTIVATION DE L'AMPK ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：RIGEL PHARMACEUTICALS INC

  公开号：WO2012016217A1

  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, 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.