tert-butyl (1-(pyridin-4-ylmethyl) piperidin-4-yl)carbamate | 1152424-96-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-butyl (1-(pyridin-4-ylmethyl) piperidin-4-yl)carbamate
• 英文别名: t-butyl [1-(pyridin-4-ylmethyl)piperidin-4-yl]carbamate；tert-Butyl 1-(pyridin-4-ylmethyl)piperidin-4-ylcarbamate；tert-butyl N-[1-(pyridin-4-ylmethyl)piperidin-4-yl]carbamate
• CAS: 1152424-96-8
• 化学式: C₁₆H₂₅N₃O₂
• mdl: MFCD17014360
• 分子量: 291.393
• InChiKey: CMMQYMDKULOWNG-UHFFFAOYSA-N

物化性质

• 沸点：
  421.5±40.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (1-(pyridin-4-ylmethyl) piperidin-4-yl)carbamate 在 盐酸 、 copper(l) iodide 、 (1R,2R)-1,2-diaminocyclohexane 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 5-(1H-pyrazol-1-yl)-N-(1-(pyridin-4-ylmethyl)piperidin-4-yl)pyridine-2-sulfonamide
  参考文献：
  名称：

  2-Phenylindole and Arylsulphonamide: Novel Scaffolds Bactericidal against Mycobacterium tuberculosis

  摘要：

  A cellular activity-based screen on Mycobacterium tuberculosis (Mtb) H37Rv using a focused library from the AstraZeneca corporate collection led to the identification of 2-phenylindoles and arylsulphonamides, novel antimycobacterial scaffolds. Both the series were bactericidal in vitro and in an intracellular macrophage infection model, active against drug sensitive and drug resistant Mtb clinical isolates, and specific to mycobacteria. The scaffolds showed promising structure-activity relationships; compounds with submicromolar cellular potency were identified during the hit to lead exploration. Furthermore, compounds from both scaffolds were tested for inhibition of known target enzymes or pathways of antimycobacterial drugs including InhA, RNA polymerase, DprE1, topoisomerases, protein synthesis, and oxidative-phosphorylation. Compounds did not inhibit any of the targets suggesting the potential of a possible novel mode of action(s). Hence, both scaffolds provide the opportunity to be developed further as leads and tool compounds to uncover novel mechanisms for tuberculosis drug discovery.

  DOI：

  10.1021/ml5001933
• 作为产物：
  描述：

  4-氯甲基吡啶盐酸盐 、 4-叔丁氧羰基氨基哌啶 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以42%的产率得到tert-butyl (1-(pyridin-4-ylmethyl) piperidin-4-yl)carbamate
  参考文献：
  名称：

  2-Phenylindole and Arylsulphonamide: Novel Scaffolds Bactericidal against Mycobacterium tuberculosis

  摘要：

  A cellular activity-based screen on Mycobacterium tuberculosis (Mtb) H37Rv using a focused library from the AstraZeneca corporate collection led to the identification of 2-phenylindoles and arylsulphonamides, novel antimycobacterial scaffolds. Both the series were bactericidal in vitro and in an intracellular macrophage infection model, active against drug sensitive and drug resistant Mtb clinical isolates, and specific to mycobacteria. The scaffolds showed promising structure-activity relationships; compounds with submicromolar cellular potency were identified during the hit to lead exploration. Furthermore, compounds from both scaffolds were tested for inhibition of known target enzymes or pathways of antimycobacterial drugs including InhA, RNA polymerase, DprE1, topoisomerases, protein synthesis, and oxidative-phosphorylation. Compounds did not inhibit any of the targets suggesting the potential of a possible novel mode of action(s). Hence, both scaffolds provide the opportunity to be developed further as leads and tool compounds to uncover novel mechanisms for tuberculosis drug discovery.

  DOI：

  10.1021/ml5001933

文献信息

• [EN] CARBOXAMIDE, SULFONAMIDE AND AMINE COMPOUNDS FOR METABOLIC DISORDERS<br/>[FR] COMPOSÉS DE CARBOXAMIDE, DE SULFONAMIDE ET D'AMINE POUR DES TROUBLES MÉTABOLIQUES
  申请人：RIGEL PHARMACEUTICALS INC

  公开号：WO2009065131A1

  公开（公告）日：2009-05-22

  Disclosed are carboxamide, sulfonamide and amine compounds, as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure in which R1, R2, R4, E, T, n 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.

  揭示了羧酰胺、磺胺酰胺和胺化合物，以及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R1、R2、R4、E、T、n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症状。
• AMPK-Activating Heterocycloalkyloxy(Hetero)Aryl Carboxamide, Sulfonamide And Amine Compounds And Methods For Using The Same
  申请人：Hong Hui

  公开号：US20120115838A1

  公开（公告）日：2012-05-10

  Disclosed are carboxamide, sulfonamide and amine compounds, as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure in which R 1 , R 2 , R 4 , E, T, n 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.

  本发明涉及羧酰胺、磺酰胺和胺类化合物，以及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R1、R2、R4、E、T、n和x如本文所述。在某些实施方式中，本文所披露的化合物可以激活AMPK通路，并可用于治疗代谢相关的疾病和症状。
• Carboxamide, Sulfonamide and Amine Compounds and Methods for Using The Same
  申请人：Hong Hui

  公开号：US20090170829A1

  公开（公告）日：2009-07-02

  Disclosed are carboxamide, sulfonamide and amine compounds, as well as pharmaceutical compositions and methods of use. One embodiment is a compound having the structure in which R 1 , R 2 , R 4 , E, T, n 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.

  本发明涉及羧酰胺、磺酰胺和胺化合物，以及制备药物组合物和使用方法。其中一种实施方式是具有下列结构的化合物： 其中R1、R2、R4、E、T、n和x的定义如本文所述。在某些实施方式中，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症状。
• CARBOXAMIDE, SULFONAMIDE AND AMINE COMPOUNDS FOR METABOLIC DISORDERS
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：EP2231600B1

  公开（公告）日：2015-07-29
• US8119809B2
  申请人：——

  公开号：US8119809B2

  公开（公告）日：2012-02-21