3-(4-benzylpiperidine-1-carbonyl)-1-methyl-3H-imidazol-1-ium iodide

• 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: 3-(4-benzylpiperidine-1-carbonyl)-1-methyl-3H-imidazol-1-ium iodide
• 英文别名: 1-[(4-benzylpiperidin-1-yl)carbonyl]-3-methyl-1H-imidazol-3-ium iodide；1-methyl-3-(4-benzyl-piperidine-1-carbonyl)-3H-imidazol-1-ium iodide；(4-benzylpiperidin-1-yl)-(3-methylimidazol-3-ium-1-yl)methanone;iodide
• 化学式: C₁₇H₂₂N₃O*I
• 分子量: 411.286
• InChiKey: BPICCHMVXSJDRK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.76
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-benzylpiperidine-1-carbonyl)-1-methyl-3H-imidazol-1-ium iodide 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 异丙醇 为溶剂， 反应 27.0h， 生成 (1R,5S)-3,7-diazabicyclo[3.3.1]nonan-3-yl(4-benzylpiperidin-1-yl)methanone fumarate
  参考文献：
  名称：

  The 3,7-diazabicyclo[3.3.1]nonane scaffold for subtype selective nicotinic acetylcholine receptor (nAChR) ligands. Part 1: The influence of different hydrogen bond acceptor systems on alkyl and (hetero)aryl substituents

  摘要：

  3,7-Diazabicyclo[3.3.1]nonane is a naturally occurring scaffold interacting with nicotinic acetylcholine receptors (nAChRs). When one nitrogen of the 3,7-diazabicyclo[3.3.1]nonane scaffold was implemented in a carboxamide motif displaying a hydrogen bond acceptor (HBA) functionality, compounds with higher affinities and subtype selectivity for alpha 4 beta 2* were obtained. The nature of the HBA system (carboxamide, sulfonamide, urea) had a strong impact on nAChR interaction. High affinity ligands for alpha 4 beta 2* possessed small alkyl chains, small un-substituted hetero-aryl groups or para-substituted phenyl ring systems along with a carboxamide group. Electrophysiological responses of selected 3,7-diazabicyclo[3.3.1]nonane derivatives to Xenopus oocytes expressing various nAChR subtypes showed diverse activation profiles. Compounds with strongest agonistic profiles were obtained with small alkyl groups whereas a shift to partial agonism/antagonism was observed for aryl substituents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.059
• 作为产物：
  描述：

  (4-benzylpiperidin-1-yl)(1H-imidazol-1-yl)methanone 生成 3-(4-benzylpiperidine-1-carbonyl)-1-methyl-3H-imidazol-1-ium iodide
  参考文献：
  名称：

  Compounds and uses thereof for decreasing activity of hormone-sensitive lipase

  摘要：

  使用化合物抑制激素敏感性脂肪酶，包括这些化合物的药物组合物，使用这些化合物和组合物的治疗方法，以及新化合物。目前的化合物是激素敏感性脂肪酶的抑制剂，可能在治疗和/或预防需要降低激素敏感性脂肪酶活性的医学疾病中有用。

  公开号：

  US20030166644A1

文献信息

• [EN] PROTEASE ACTIVATED RECEPTOR 2 (PAR2) ANTAGONISTS<br/>[FR] ANTAGONISTES DU RÉCEPTEUR 2 ACTIVÉ PAR DES PROTÉASES (PAR2)
  申请人：PROXIMAGEN LTD

  公开号：WO2012101453A1

  公开（公告）日：2012-08-02

  A compound of formula (I) or a pharmaceutically acceptable salt, solvate, hydrate thereof (I) Wherein Y, Z, R3, U, R4, m and n are as defined in the claims.

  式(I)的化合物或其药学上可接受的盐、溶剂化物、水合物，其中Y、Z、R3、U、R4、m和n如权利要求中所定义。
• Synthesis and Structure−Activity Relationship for a Novel Class of Potent and Selective Carbamate-Based Inhibitors of Hormone Selective Lipase with Acute In Vivo Antilipolytic Effects
  作者：Søren Ebdrup、Hanne Hoffmann Frølund Refsgaard、Christian Fledelius、Poul Jacobsen

  DOI：10.1021/jm0607653

  日期：2007.11.1

  inhibitors 4-hydroxymethyl-piperidine-1-carboxylic acid 4-(5-trifluoromethylpyridin-2-yloxy)-phenyl ester (13f) and 4-hydroxy-piperidine-1-carboxylic acid 4-(5-trifluoromethylpyridin-2-yloxy)-phenyl ester (13g), with IC50 values of 110 and 500 nM, respectively. Both inhibitors were active in acute antilipolytic experiments in vivo and none of the inhibitors inhibited the cytochrome P450 (CYP) isoforms 2D6,

  激素敏感性脂肪酶（HSL）是一种细胞内酶，在脂肪酸代谢的调节中具有重要作用。因此，该酶是用于治疗胰岛素抵抗和血脂异常的潜在的潜在药理靶标。基于高通量筛选，鉴定出了基于氨基甲酸酯的HSL抑制剂，并将其优化为选择性HSL抑制剂4-羟甲基-哌啶-1-甲酸4-（5-三氟甲基吡啶-2-基氧基）-苯基酯（13f）和4 -羟基-哌啶-1-羧酸4-（5-三氟甲基吡啶-2-基氧基）-苯基酯（13g），IC50值分别为110和500 nM。两种抑制剂在体内急性抗脂解实验中均具有活性，并且没有一种抑制剂可抑制细胞色素P450（CYP）同工型2D6、3A4和1A2。
• Use of compounds for decreasing activity of hormone-sensitive
  申请人：——

  公开号：US20030166690A1

  公开（公告）日：2003-09-04

  Use of compounds to inhibit hormone-sensitive lipase, pharmaceutical compositions comprising the compounds, methods of treatment employing these compounds and compositions, and novel compounds. The present compounds are inhibitors of hormone-sensitive lipase and may be useful in the treatment and/or prevention of medical disorders where a decreased activity of hormone-sensitive lipase is desirable.

  使用化合物来抑制激素敏感性脂肪酶，包括这些化合物的制药组合物，使用这些化合物和组合物的治疗方法，以及新颖的化合物。这些化合物是激素敏感性脂肪酶的抑制剂，可用于治疗和/或预防需要降低激素敏感性脂肪酶活性的医学疾病。
• Use of compounds for decreasing activity of hormone-sensitive lipase
  申请人：Nero Nordisk A/S

  公开号：US07067517B2

  公开（公告）日：2006-06-27

  Use of compounds to inhibit hormone-sensitive lipase, pharmaceutical compositions comprising the compounds, methods of treatment employing these compounds and compositions, and novel compounds. The present compounds are inhibitors of hormone-sensitive lipase and may be useful in the treatment and/or prevention of medical disorders where a decreased activity of hormone-sensitive lipase is desirable.

  使用化合物抑制荷尔蒙敏感性脂肪酶，包括这些化合物的制药组合物，使用这些化合物和组合物的治疗方法，以及新型化合物。这些化合物是荷尔蒙敏感性脂肪酶的抑制剂，可能在需要降低荷尔蒙敏感性脂肪酶活性的医疗障碍的治疗和/或预防中有用。
• Ureas with histamine H3-antagonist receptor activity—A new scaffold discovered by lead-hopping from cinnamic acid amides
  作者：Jesper F. Lau、Claus Bekker Jeppesen、Karin Rimvall、Rolf Hohlweg

  DOI：10.1016/j.bmcl.2006.07.093

  日期：2006.10

  A group of tri and tetrasubstituted urea derivatives have been found to be hH(3)-antagonists. The most potent compounds were found in the class of (piperazine-1-yl)-(piperidine-1-yl)-methanones which in addition showed negligible hERG inhibition. (c) 2006 Elsevier Ltd. All rights reserved.