(1-pentyl-4-piperidyl)methylamine | 258345-25-4

• 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: (1-pentyl-4-piperidyl)methylamine
• 英文别名: 4-Aminomethyl-1-pentyl-piperidine；4-Aminomethyl-1-pentylpiperidine；(1-pentylpiperidin-4-yl)methanamine
• CAS: 258345-25-4
• 化学式: C₁₁H₂₄N₂
• 分子量: 184.325
• InChiKey: FZBOVKNUBQJHSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  5
• 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：

  甘氨熊胆酸 、 (1-pentyl-4-piperidyl)methylamine 以to give 0.210 g of the title compound as a white solid (Et2O)的产率得到(2S)-1-(9H-Carbazol-4-yloxy)-3-[(1-pentyl-piperidin-4-ylmethyl)-amino]-propan-2-ol
  参考文献：
  名称：

  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

  摘要：

  该发明提供了公式I的化合物，其结构如下：1其中A，B，Z，R和R1如前所定义，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性疾病（通常与肥胖或葡萄糖不耐症有关），动脉硬化，胃肠道疾病，神经遗传性炎症，青光眼，眼压增高和频繁排尿; 特别适用于治疗或抑制2型糖尿病。

  公开号：

  US20020037907A1
• 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 (1-pentyl-4-piperidyl)methylamine
  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 &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。
• Benzimidazole derivatives. Part 1: Synthesis and structure–activity relationships of new benzimidazole-4-carboxamides and carboxylates as potent and selective 5-HT4 receptor antagonists
  作者：Marı́a L. López-Rodrı́guez、Bellinda Benhamú、Alma Viso、M.José Morcillo、Marta Murcia、Luis Orensanz、M.José Alfaro、M.Isabel Martı́n

  DOI：10.1016/s0968-0896(99)00172-8

  日期：1999.11

  New benzimidazole-4-carboxamides 1-16 and -carboxylates 17-26 were synthesized and evaluated for binding affinity at serotonergic 5-HT4 and 5-HT3 receptors in the CNS. Most of the synthesized compounds exhibited moderate to-very high affinity tin many cases subnanomolar) for the 5-HT4 binding site and no significant affinity for the 5-HT3 receptor. SAR observations and structural analyses (molecular modeling, INSIGHT II) indicated that the presence of a voluminous substituent in the basic nitrogen atom of the amino moiety and a distance of ca. 8.0 Angstrom from this nitrogen to the aromatic ring are of great importance for high affinity and selectivity for 5-HT4 receptors. These results confirm our recently proposed model for recognition by the 5-HT4 binding site. Amides 12-15 and esters 24 and 25 bound at central 5-HT4 sites with very high affinity (K-j = 0.11-2.9 nM) and excellent selectivity over serotonin 5-HT3, 5-HT2A, and S-HT1A receptors (K-i > 1000-10,000 nM). Analogues 12 (k(i)(5-HT4) = 0.32 nM), 13 (K-i(5-HT4)= 0.11 nM), 14 (K-i(5-HT4) = 0.29 nM) and 15 (K-i(5-HT4) = 0.54 nM) were pharmacologically characterized as selective 5-HT4 antagonists in the isolated guinea pig ileum (pA(2) = 7.6, 7.9, 8.2 and 7.9, respectively), with a potency comparable to the 5-HT4 receptor antagonist RS 39604 (pA(2) = 8.2). The benzimidazoe-4-carboxylic acid derivatives described in this paper represent a novel class of potent and selective 5-HT4 receptor antagonists. In particular, compounds 12-15 could be interesting pharmacological tools for the understanding of the role of 5-HT4 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.