The synthesis of new adenosine A3 selective ligands containing bioisosteric isoxazoles

被引:22
|
作者
Mogensen, JP
Roberts, SM
Bowler, AN
Thomsen, C
Knutsen, LJS
机构
[1] Novo Nordisk AS, Hlth Care Discovery, DK-2760 Malov, Denmark
[2] Univ Liverpool, Dept Chem, Liverpool L69 3BX, Merseyside, England
关键词
D O I
10.1016/S0960-894X(98)00302-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis and purinergic receptor binding of novel adenosine A, ligands is described. Many selective A, receptor agonists e.g. N-(3-iodobenzyl)adenosine-5'-methyluronamide (IB-MECA) contain a 4'-ribosylalkylamide moiety. We found that this amide and other 4'-functional groups could be replaced with an isosteric isoxazole, and the target molecules retained potent binding to the recombinant human A, receptor. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1767 / 1770
页数:4
相关论文
共 50 条
  • [41] LIGANDS FOR BRAIN CHOLINERGIC CHANNEL RECEPTORS - SYNTHESIS AND IN-VITRO CHARACTERIZATION OF NOVEL ISOXAZOLES AND ISOTHIAZOLES AS BIOISOSTERIC REPLACEMENTS FOR THE PYRIDINE RING IN NICOTINE
    GARVEY, DS
    WASICAK, JT
    ELLIOTT, RL
    LEBOLD, SA
    HETTINGER, AM
    CARRERA, GM
    LIN, NH
    HE, Y
    HOLLADAY, MW
    ANDERSON, DJ
    CADMAN, ED
    RASZKIEWICZ, JL
    SULLIVAN, JP
    ARNERIC, SP
    JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (26) : 4455 - 4463
  • [42] Erratum to: Molecular modelling study of 2-phenylethynyladenosine (PEAdo) derivatives as highly selective A3 adenosine receptor ligands
    Diego Dal Ben
    Catia Lambertucci
    Sara Taffi
    Sauro Vittori
    Rosaria Volpini
    Karl-Norbert Klotz
    Gloria Cristalli
    Purinergic Signalling, 2007, 3 (1-2) : 181 - 181
  • [43] N6-methoxy-2-alkynyladenosine derivatives as highly potent and selective ligands at the human A3 adenosine receptor
    Volpini, Rosaria
    Dal Ben, Diego
    Lambertucci, Catia
    Taffi, Sara
    Vittori, Sauro
    Klotz, Karl-Norbert
    Cristalli, Gloria
    JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (06) : 1222 - 1230
  • [44] Selective A3 adenosine receptor antagonists derived from nucleosides containing a bicyclo[3.1.0]hexane ring system
    Melman, Artem
    Wang, Ben
    Joshi, Bhalchandra V.
    Gao, Zhan-Guo
    de Castro, Sonia
    Heller, Cara L.
    Kim, Soo-Kyung
    Jeong, Lak Shin
    Jacobson, Kenneth A.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (18) : 8546 - 8556
  • [45] Functionalized Congeners of A3 Adenosine Receptor-Selective Nucleosides Containing a Bicyclo[3.1.0]hexane Ring System
    Tosh, Dilip K.
    Chinn, Moshe
    Ivanov, Andrei A.
    Klutz, Athena M.
    Gao, Zhan-Guo
    Jacobson, Kenneth A.
    JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (23) : 7580 - 7592
  • [46] Progress in the development of small molecules as new human A3 adenosine receptor ligands based on the 3-thiophenylcoumarin core
    Matos, M. J.
    Vilar, S.
    Kachler, S.
    Vazquez-Rodriguez, S.
    Varela, C.
    Delogu, G.
    Hripcsak, G.
    Santana, L.
    Uriarte, E.
    Klotz, K. -N.
    Borges, F.
    MEDCHEMCOMM, 2016, 7 (05) : 845 - 852
  • [47] New high affinity agonists at A3 adenosine receptors
    Klotz, KN
    Volpini, R
    Vittori, S
    Cristalli, G
    NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1998, 357 (04) : R32 - R32
  • [48] A new role for adenosine A3 receptors in chronic neuroinflammation
    van der Putten, Celine
    Ella, Zuiderwijk-Sick A.
    van Straalen, Linda
    Eveline, de Geus D.
    Leonie, Boven A.
    Ivanela, Kondova
    Ad, Ijzerman P.
    Jeffrey, Bajramovic J.
    JOURNAL OF NEUROIMMUNOLOGY, 2010, 228 (1-2) : 163 - 163
  • [49] A NEW ROLE FOR ADENOSINE A3 RECEPTORS IN CHRONIC NEUROINFLAMMATION
    Bajramovic, J. J.
    van der Putten, C.
    Zuiderwijk-Sick, E. A.
    van Straalen, L.
    de Geus, E. D.
    Boven, L. A.
    Kondova, I
    Ijzerman, A. P.
    GLIA, 2011, 59 : S151 - S152
  • [50] Engineering of A3 adenosine and P2Y nucleotide receptors and their ligands
    Jacobson, KA
    Kim, HS
    Ravi, G
    Kim, SKY
    Lee, K
    Chen, AS
    Chen, WZ
    Kim, SG
    Barak, D
    Liang, BT
    Gao, ZG
    DRUG DEVELOPMENT RESEARCH, 2003, 58 (04) : 330 - 339