2-Amino-5-aryl-pyridines as selective CB2 agonists: Synthesis and investigation of structure-activity relationships

被引:11
|
作者
Gleave, Robert J. [1 ]
Beswick, Paul J. [1 ]
Brown, Andrew J. [1 ]
Giblin, Gerard M. P. [1 ]
Haslam, Carl P. [1 ]
Livermore, David [1 ]
Moses, Andrew [1 ]
Nicholson, Neville H. [1 ]
Page, Lee W. [1 ]
Slingsby, Brian [1 ]
Swarbrick, Martin E. [1 ]
机构
[1] GlaxoSmithKline, Neurosci Ctr Excellence Drug Discovery, Pain & Neuroexcitabil Discovery Performance Unit, Harlow CM19 5AW, Essex, England
关键词
Cannabinoid; CB2; CB1; SAR; CANNABINOID RECEPTOR; PHARMACOLOGY;
D O I
10.1016/j.bmcl.2009.10.041
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
2-Amino-5-aryl-pyridines, exemplified by compound 1, had been identified as a synthetically tractable series of CB2 agonists from a high-throughput screen of the GlaxoSmithKline compound collection. Described herein are the results of an investigation of the structure-activity relationships (SAR) which led to the identification a number of potent and selective agonists. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6578 / 6581
页数:4
相关论文
共 50 条
  • [31] Variously substituted 2-oxopyridine derivatives: Extending the structure-activity relationships for allosteric modulation of the cannabinoid CB2 receptor
    Gado, Francesca
    Mohamed, Kawthar A.
    Meini, Serena
    Ferrisi, Rebecca
    Bertini, Simone
    Digiacomo, Maria
    D'Andrea, Felicia
    Stevenson, Lesley A.
    Laprairie, Robert B.
    Pertwee, Roger G.
    Manera, Clementina
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2021, 211
  • [32] Therapeutic Utility of Cannabinoid Receptor Type 2 (CB2) Selective Agonists
    Han, Sangdon
    Thatte, Jayant
    Buzard, Daniel J.
    Jones, Robert M.
    JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (21) : 8224 - 8256
  • [33] Synthesis and structure-activity relationships of a series of benzazepine derivatives as 5-HT2C receptor agonists
    Shimada, Itsuro
    Maeno, Kyoichi
    Kondoh, Yutaka
    Kaku, Hidetaka
    Sugasawa, Keizo
    Kimura, Yasuharu
    Hatanaka, Ken-Ichi
    Naitou, Yuki
    Wanibuchi, Furnikazu
    Sakamoto, Shuichi
    Tsukamoto, Shin-ichi
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (06) : 3309 - 3320
  • [34] Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2c Agonists
    Hansen, Martin
    Phonekeo, Karina
    Paine, James S.
    Leth-Petersen, Sebastian
    Begtrup, Mikael
    Braeuner-Osborne, Hans
    Kristensen, Jesper L.
    ACS CHEMICAL NEUROSCIENCE, 2014, 5 (03): : 243 - 249
  • [35] Structure-activity relationships of dinucleotides: Potent and selective agonists of P2Y receptors
    Shaver S.R.
    Rideout J.L.
    Pendergast W.
    Douglass J.G.
    Brown E.G.
    Boyer J.L.
    Patel R.I.
    Redick C.C.
    Jones A.C.
    Picher M.
    Yerxa B.R.
    Purinergic Signalling, 2005, 1 (2) : 183 - 191
  • [36] The SAR studies of novel CB2 selective agonists, benzimidazolone derivatives
    Omura, Hirofumi
    Kawai, Makoto
    Shima, Akiko
    Iwata, Yasuhiro
    Ito, Fumitaka
    Masuda, Tsutomu
    Ohta, Atsuko
    Makita, Naoya
    Omoto, Kiyoyuki
    Sugimoto, Hiromi
    Kikuchi, Akira
    Iwata, Hiroshi
    Ando, Kazuo
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (11) : 3310 - 3314
  • [37] Optimisation of a novel series of selective CNS penetrant CB2 agonists
    Watson, Christine
    Owen, Dafydd R.
    Harding, Denise
    Kon-I, Kana
    Lewis, Mark L.
    Mason, Helen J.
    Matsumizu, Miyako
    Mukaiyama, Takasuke
    Rodriguez-Lens, Margarita
    Shima, Akiko
    Takeuchi, Mifune
    Tran, Isabelle
    Young, Tim
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (14) : 4284 - 4287
  • [38] Discovery and optimization of novel purines as potent and selective CB2 agonists
    Hollinshead, Sean P.
    Astles, Peter C.
    Chambers, Mark G.
    Johnson, Michael P.
    Palmer, John
    Tidwell, Michael W.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (15) : 4962 - 4966
  • [39] Novel azoles as potent and selective cannabinoid CB2 receptor agonists
    Harnett, Jeremiah J.
    Dolo, Christine
    Viossat, Isabelle
    Auger, Florence
    Ferrandis, Eric
    Bigg, Dennis
    Auguet, Michel
    Auvin, Serge
    Chabrier, Pierre-E.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (01) : 88 - 91
  • [40] Synthesis, Pharmacological Characterization, and Structure-Activity Relationships of Noncanonical Selective Agonists for α7 nAChRs
    Camacho-Hernandez, Gisela Andrea
    Stokes, Clare
    Duggan, Brendan M.
    Kaczanowska, Katarzyna
    Brandao-Araiza, Stefania
    Doan, Lisa
    Papke, Roger L.
    Taylor, Palmer
    JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (22) : 10376 - 10390