4-(4-羟基哌啶-1-甲基)-苯甲腈 | 887593-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-(4-羟基哌啶-1-甲基)-苯甲腈
• 中文别名: 4-[(4-羟基-1-哌啶基)甲基]苯腈；4-(4-羟基-哌啶-1-基甲基)-苯甲腈
• 英文名称: 1-(4-cyanobenzyl)piperidin-4-ol
• 英文别名: 4-((4-Hydroxypiperidin-1-yl)methyl)benzonitrile；4-[(4-hydroxypiperidin-1-yl)methyl]benzonitrile
• CAS: 887593-88-6
• 化学式: C₁₃H₁₆N₂O
• mdl: MFCD06656916
• 分子量: 216.283
• InChiKey: NYAOZPISCGYEAV-UHFFFAOYSA-N

物化性质

• 密度：
  1.17

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-羟基哌啶-1-甲基)-苯甲腈 在 吡啶 sodium hydride 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.5h， 生成 N-(4-cyanobenzyl)-3-(4-cyanobenzylidinyl)piperidine
  参考文献：
  名称：

  Trypanocidal Activity of Conformationally Restricted Pentamidine Congeners

  摘要：

  A series of conformationally restricted congeners of pentamidine in which the flexible pentyl bridge of pentamidine was replaced by trans-1,2-bismethylenecyclopropyl, phenyl, pyridinyl, piperazinyl, homopiperazinyl, and piperidinyl groups were synthesized. The compounds were evaluated for trypanocidal activity in vitro and in vivo against one drug-sensitive and three drug-resistant trypanosome isolates. The DNA binding affinity of the compounds was also studied using calf thymus DNA and poly(dA-dT). The nature of the linker influenced the DNA binding affinity as well as the trypanocidal activity of the compounds. trans-1,2-Bis(4-amidinophenoxymethylene)cyclopropane (1) was over 25-fold more potent than pentamidine against the drug-resistant isolate KETRI 243As-10-3, albeit with comparable DNA binding affinity. NN'-Bis(4-amidinophenyl)homopiperazine (8) was the most potent trypanocide in vitro against all four trypanosome isolates studied, but N,N'-bis(4-amidinophenyl)piperazine (6) was the most effective agent in vivo against both drug-sensitive and drug-resistant trypanosomes.

  DOI：

  10.1021/jm020375q
• 作为产物：
  描述：

  4-羟基哌啶 、 对氰基溴化苄 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到4-(4-羟基哌啶-1-甲基)-苯甲腈
  参考文献：
  名称：

  Trypanocidal Activity of Conformationally Restricted Pentamidine Congeners

  摘要：

  A series of conformationally restricted congeners of pentamidine in which the flexible pentyl bridge of pentamidine was replaced by trans-1,2-bismethylenecyclopropyl, phenyl, pyridinyl, piperazinyl, homopiperazinyl, and piperidinyl groups were synthesized. The compounds were evaluated for trypanocidal activity in vitro and in vivo against one drug-sensitive and three drug-resistant trypanosome isolates. The DNA binding affinity of the compounds was also studied using calf thymus DNA and poly(dA-dT). The nature of the linker influenced the DNA binding affinity as well as the trypanocidal activity of the compounds. trans-1,2-Bis(4-amidinophenoxymethylene)cyclopropane (1) was over 25-fold more potent than pentamidine against the drug-resistant isolate KETRI 243As-10-3, albeit with comparable DNA binding affinity. NN'-Bis(4-amidinophenyl)homopiperazine (8) was the most potent trypanocide in vitro against all four trypanosome isolates studied, but N,N'-bis(4-amidinophenyl)piperazine (6) was the most effective agent in vivo against both drug-sensitive and drug-resistant trypanosomes.

  DOI：

  10.1021/jm020375q

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。
• Synthesis and anti-pneumocystis carinii activity of piperidine-linked aromatic diimidazolines
  作者：Tien L. Huang、Qian Zhang、Angele T. White、Sherry F. Queener、Marilyn S. Bartlett、James W. Smith、Isaac O. Donkor

  DOI：10.1016/0960-894x(96)00373-3

  日期：1996.9

  A series of novel piperidine-linked aromatic diimidazolines (3-7) have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii drug, Pentamidine. These compounds significantly inhibited the growth of Pneumocystis carinii in culture at 1 mu g/mL. Copyright (C) 1996 Elsevier Science Ltd
• CARBOXAMIDE, SULFONAMIDE AND AMINE COMPOUNDS FOR METABOLIC DISORDERS
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：EP2231600A1

  公开（公告）日：2010-09-29