4-Aminomethyl-1-hexyl-piperidine | 246544-68-3

• 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: 4-Aminomethyl-1-hexyl-piperidine
• 英文别名: (1-hexylpiperidin-4-yl)methanamine
• CAS: 246544-68-3
• 化学式: C₁₂H₂₆N₂
• 分子量: 198.352
• InChiKey: QUXYQVPKJMGNJS-UHFFFAOYSA-N

物化性质

• 沸点：
  258.3±8.0 °C(Predicted)
• 密度：
  0.878±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氨基-5-氯-2-甲氧基苯甲酸 、 4-Aminomethyl-1-hexyl-piperidine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到4-amino-5-chloro-N-[(1-hexyl-4-piperidinyl)methyl]-2-methoxybenzamide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of carboxamide derivatives as selective serotoninergic 5-HT4 receptor agonists

  摘要：

  A number of new carboxamide derivatives were synthesized. The affinity of these compounds for the serotoninergic 5-HT4 receptor was evaluated by use of radioligand-binding techniques. The agonistic activity was evaluated as the contractile effect of the ascending colon isolated from guinea-pigs. Among these compounds, 4-amino-5-chloro-2-methoxy-N-[1-[2-[(methylsulfonyl)amino]ethly]-4-piperidinylmethyl]benzamide (24) showed a high affinity for the 5-HT4 receptor (Ki = 9.6 nM). Compound 24 displayed a higher affinity for 5-HT4 receptors than the other receptors, including, 5-HT3 and dopamine D-2 receptors. In addition, compound 24 was confirmed to be a potent 5-HT4 receptor agonist (ED50 - 7.0 nM). An interaction model between compound 24 and 5-HT4 receptor was proposed. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80083-x
• 作为产物：
  描述：

  4-Boc-氨甲基哌啶 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 4-Aminomethyl-1-hexyl-piperidine
  参考文献：
  名称：

  Novel substituted 4-aminomethylpiperidines as potent and selective human β3-agonists. Part 1: aryloxypropanolaminomethylpiperidines

  摘要：

  The synthesis and SAR of a series of human beta(3) adrenoreceptor agonists based on a template derived from a common pharmacophore coupled with 4-aminomethylpiperidine is described. Potent and selective agents were identified such as 26 that was in vitro active in CHO cells expressing human beta(3)-AR (EC50 = 49 nNl, IA = 1.1), and in vivo active in a transgenic mouse model. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00607-8

文献信息

• Substituted 2- (S) -hydroxy-3- (piperidin-4-yl-methylamino) -propyl ethers and substituted 2-aryl-2- (R) - hydroxy-1- (piperidin-4-yl-methyl) -ethylamine beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020037907A1

  公开（公告）日：2002-03-28

  This invention provides compounds of Formula I having the structure 1 wherein A, B, Z, R and R 1 are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  这项发明提供了具有结构式1的化合物，其中A、B、Z、R和R1如前文所定义，或其药学上可接受的盐，用于治疗或抑制与胰岛素抵抗或高血糖相关的代谢紊乱（通常与肥胖或葡萄糖不耐受有关）、动脉粥样硬化、胃肠道疾病、神经炎症、青光眼、眼压增高和频繁排尿；特别适用于治疗或抑制2型糖尿病。
• Substituted 2-(S)-hydroxy-3-(piperidin-4-yl-methylamino)-propyl ethers and substituted 2-aryl-2-(R)-hydroxy-1-(piperidin-4-yl-methyl)-ethylamine &bgr;-3 adrenergic receptor agonists
  申请人：Wyeth

  公开号：US06506901B2

  公开（公告）日：2003-01-14

  This invention provides compounds of Formula I having the structure wherein A, B, Z, R and R1 are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  本发明提供具有式I的化合物，其结构中A、B、Z、R和R1如前所定义，或其药学上可接受的盐，这些化合物在治疗或抑制与胰岛素抵抗或高血糖相关的代谢紊乱（通常与肥胖或葡萄糖耐受性不良有关）、动脉粥样硬化、胃肠道疾病、神经遗传性炎症、青光眼、眼压增高和频繁排尿方面非常有用；并且在治疗或抑制II型糖尿病方面特别有用。
• Design, synthesis, and pharmacological evaluation of 2-(1-(1,3,4-thiadiazol-2-yl)piperidin-4-yl)ethan-1-ol analogs as novel glutaminase 1 inhibitors
  作者：Tao Yang、Yang Tian、Yingxue Yang、Minghai Tang、Mingsong Shi、Yong Chen、Zhuang Yang、Lijuan Chen

  DOI：10.1016/j.ejmech.2022.114686

  日期：2022.12

  In this study, we described a series of 2-(1-(1,3,4-thiadiazol-2-yl)piperidin-4-yl)ethan-1-ol analogs as selective GLS1 inhibitors. Systematic exploration of the structure-activity relationship through introducing the hydrophilic skeleton and different chains based on BPTES led to the discovery of the superior derivative compound 24y. Compound 24y showed excellent potency on GLS1 kinase with an IC50

  在这项研究中，我们描述了一系列 2-(1-(1,3,4-thiadiazol-2-yl)piperidin-4-yl)ethan-1-ol 类似物作为选择性 GLS1 抑制剂。通过引入基于BPTES的亲水骨架和不同链系统探索构效关系，发现了优越的衍生化合物24y。化合物24y对 GLS1 激酶表现出优异的效力，IC 50值为 68 nM，对 GLS2 的选择性高出 220 倍以上。此外，体外研究表明，化合物24y在线粒体 GLS1 通路上发挥作用，即上调 ROS 水平。复合24y还表现出相对良好的代谢稳定性，生物利用度为 12.4%。此外，化合物24y在 A549 和 HCT116 异种移植肿瘤模型中显示出抗肿瘤活性，口服管饲 100 mg/kg 的肿瘤生长抑制率分别为 40.9% 和 42.0%。总之，这些发现表明化合物24y是一种有效的 GLS1 抑制剂，为开发新型 GLS1 抑制剂提供了新策略。
• US6506901B2
  申请人：——

  公开号：US6506901B2

  公开（公告）日：2003-01-14
• [EN] SUBSTITUTED 2-(S)-HYDROXY-3-(PIPERIDIN-4-YL-METHYLAMINO)-PROPYL ETHERS AND SUBSTITUTED 2-ARYL-2-(R)-HYDROXY-1-(PIPERIDIN-4-YL-METHYL)-ETHYLAMINE BETA-3 ADRENERGIC RECEPTOR AGONISTS<br/>[FR] AGONISTES VIS-A-VIS DE RECEPTEUR ADRENERGIQUE BETA 3 DE 2-(S)-HYDROXY-3-(PIPERIDINE-4-YL-METHYLAMINO)-PROPYL ETHERS SUBSTITUES ET DE 2-ARYL-2-(R)-HYDROXY-1-(PIPERIDINE-4-YL-METHYL)-ETHYLAMINE SUBSTITUEE
  申请人：AMERICAN HOME PROD

  公开号：WO2002006255A2

  公开（公告）日：2002-01-24

  The invention provides compounds of Formula (I) having the structure wherein A, B, Z, R and R1 are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.