5-(4-benzylpiperidin-1-yl)pentan-1-amine | 763907-77-3

• 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: 5-(4-benzylpiperidin-1-yl)pentan-1-amine
• CAS: 763907-77-3
• 化学式: C₁₇H₂₈N₂
• 分子量: 260.423
• InChiKey: XIPKUTGYFWQYJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  异氰酸间氰基苯酯 、 5-(4-benzylpiperidin-1-yl)pentan-1-amine 以 四氢呋喃 为溶剂， 生成 1-[5-(4-Benzyl-piperidin-1-yl)-pentyl]-3-(3-cyano-phenyl)-urea
  参考文献：
  名称：

  CCR3 antagonists: a potential new therapy for the treatment of asthma. Discovery and structure–activity relationships

  摘要：

  CCR3 antagonist leads with IC50 values in the muM range were converted into low nM binding compounds that displayed in vitro inhibition of human eosinophil chemotaxis induced by human eotaxin. In particular, 4-benzylpiperidin-1-yl-n-propylureas and erythro-3-(4-benzyl-2-(alpha-hydroxyalkyl)piperidin-1-yl)-n-propylureas (obtained via Beak reaction of N-BOC-4-benzylpiperidine) exhibited single digit nanomolar IC50 values for CCR3. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00206-8
• 作为产物：
  描述：

  5-溴戊腈 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 20.0h， 生成 5-(4-benzylpiperidin-1-yl)pentan-1-amine
  参考文献：
  名称：

  [EN] N-ACYLETHANOLAMINE HYDROLYZING ACID AMIDASE (NAAA) INHIBITORS AND THEIR USE THEREOF
  [FR] INHIBITEURS D'AMIDASE ACIDE (NAAA) HYDROLYSANT LA N-ACYLÉTHANOLAMINE ET LEUR UTILISATION

  摘要：

  一种化合物被表示为化学式I，其互变异构体、立体异构体或其药学上可接受的盐。化学式I的化合物是N-酰乙醇胺水解酸酰胺酶（NAAA）的抑制剂。本技术涉及到抑制N-酰乙醇胺水解酸酰胺酶的化合物、组合物和方法，以及治疗受试者中的N-酰乙醇胺水解酸酰胺酶介导的疾病。

  公开号：

  WO2015179190A1

文献信息

• N-acylethanolamine hydrolyzing acid amidase (NAAA) inhibitors and their use thereof
  申请人：Northeastern University

  公开号：US10640494B2

  公开（公告）日：2020-05-05

  A compound is represented as Formula I, a tautomer thereof, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof: Compounds of Formula I are inhibitors of N-acylethanolamine hydrolyzing acid amidase (NAAA).

  一种化合物表示为式 I、其同分异构体、立体异构体或其药学上可接受的盐： 式 I 的化合物是 N-酰乙醇胺水解酸酰胺酶（NAAA）的抑制剂。
• Sigma Receptor Ligands Carrying a Nitric Oxide Donor Nitrate Moiety: Synthesis, In Silico, and Biological Evaluation
  作者：Emanuele Amata、Maria Dichiara、Davide Gentile、Agostino Marrazzo、Rita Turnaturi、Emanuela Arena、Alfonsina La Mantia、Barbara Rita Tomasello、Rosaria Acquaviva、Claudia Di Giacomo、Antonio Rescifina、Orazio Prezzavento

  DOI：10.1021/acsmedchemlett.9b00661

  日期：2020.5.14

  We report the development of molecular hybrids in which a nitrate group serving as nitric oxide (NO) donor is covalently joined to sigma receptor ligands to give candidates for double-targeted cancer therapy. The compounds have been evaluated in radioligand binding assay at both sigma receptors and selected compounds tested for NO release. Compounds 9, 15, 18, 19, and 21 were subjected to MTT test. Compound 15 produced a significant reduction of MCF-7 and Caco-2 cellular viability with comparable IC50 as doxorubicin, being also not toxic for fibroblast HFF-1 cells. Compound 15 has shown a sigma(1), receptor antagonist/sigma(2) receptor agonist profile. Two derivatives of compound 15 lacking the nitrate group did not induce a reduction of MCF-7 cellular viability, suggesting a potential synergistic effect between the sigma receptors and the NO-mediated events. Overall, the combination of NO donor and sigma receptors ligands provided compounds with beneficial effects for the treatment of cancer.
• N-Acylethanolamine Hydrolyzing Acid Amidase (NAAA) Inhibitors And Their Use Thereof
  申请人：NORTHEASTERN UNIVERSITY

  公开号：US20170114050A1

  公开（公告）日：2017-04-27

  A compound is represented as Formula I, a tautomer thereof, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. Compounds of Formula I are inhibitors of N-acylethanolamine hydrolyzing acid amidase (NAAA). The present technology is directed to compounds, compositions, and methods to inhibit N-acylethanolamine hydrolyzing acid amidase and to treat N-acylethanolamine hydrolyzing acid amidase mediated conditions in a subject.
• US9963444B2
  申请人：——

  公开号：US9963444B2

  公开（公告）日：2018-05-08