Design, synthesis, and SAR analysis of novel selective σ1 ligands

被引：30
作者：
Collina, Siniona
Loddo, Guya
Urbano, Mariangela
Linati, Laura
Callegari, Athos
Ortuso, Francesco
Alcaro, Stefano
Laggner, Christian
Langer, Thierry
Prezzavento, Orazio
Ronsisvalle, Giuseppe
Azzolina, Ornella
机构：
[1] Univ Pavia, Dipartimento Chim Farmaceut, I-27100 Pavia, Italy
[2] Univ Pavia, Ctr Grandi Strumenti, I-27100 Pavia, Italy
[3] Univ Pavia, Dipartimento Sci Terra, I-27100 Pavia, Italy
[4] Univ Catanzaro Magna Graecia, Dipartimento Sci Farmacol Compleso Nini Barbieri, I-88021 Roccelletta Di Borgia, CZ, Italy
[5] Univ Innsbruck, Dept Pharmaceut Chem, A-6020 Innsbruck, Austria
[6] Univ Innsbruck, Ctr Mol Biosci CMBI, A-6020 Innsbruck, Austria
[7] Univ Catania, Dipartimento Sci Farmaceut, I-95125 Catania, Italy
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 02期
关键词：
arylalkylamines; sigma receptors; molecular modeling; SAR studies;
D O I：
10.1016/j.bmc.2006.10.048
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A new series of arylalkyl- and alkenylamines was designed, synthesized, and evaluated for binding to sigma(1) and sigma(2) receptors. Many compounds exhibited nanomolar affinity for sigma(1) subtype receptor with good selectivity over sigma(2). A molecular modeling study was conducted in order to rationalize the experimental data, and the structure-receptor affinities are discussed. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：771 / 783
页数：13
相关论文
共 34 条
  • [1] Chemical and biological profile of racemic and optically active dialkylaminoalkylnaphthalenes with analgesic activity
    Azzolina, O
    Collina, S
    Brusotti, G
    Rossi, D
    Callegari, A
    Linati, L
    Barbieri, A
    Ghislandi, V
    [J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (10) : 1073 - 1081
  • [2] AZZOLINA O, 2001, 1 MAGN GREC MED CHEM
  • [3] Microwave-induced organic reaction enhancement (MORE) chemistry. Part 13. Microwave-assisted rapid and simplified hydrogenation
    Banik, BK
    Barakat, KJ
    Wagle, DR
    Manhas, MS
    Bose, AK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) : 5746 - 5753
  • [4] Bowen W D, 2000, Pharm Acta Helv, V74, P211
  • [5] AN INTERNAL COORDINATE MONTE-CARLO METHOD FOR SEARCHING CONFORMATIONAL SPACE
    CHANG, G
    GUIDA, WC
    STILL, WC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4379 - 4386
  • [6] CHIEN CC, 1994, J PHARMACOL EXP THER, V271, P1583
  • [7] Microwave assisted synthesis of chiral pyrrolines with biological activity
    Collina, S
    Loddo, G
    Barbieri, A
    Linati, L
    Alcaro, S
    Chimenti, P
    Azzolina, O
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (22) : 3601 - 3608
  • [8] CHARACTERIZATION OF THE BINDING OF [H-3] (+)-PENTAZOCINE TO SIGMA-RECOGNITION SITES IN GUINEA-PIG BRAIN
    DEHAVENHUDKINS, DL
    FLEISSNER, LC
    FORDRICE, FY
    [J]. EUROPEAN JOURNAL OF PHARMACOLOGY-MOLECULAR PHARMACOLOGY SECTION, 1992, 227 (04): : 371 - 378
  • [9] Farrugia L.J., 1997, J APPL CRYSTALLOGR, V30, P565
  • [10] STRUCTURAL FEATURES IMPORTANT FOR SIGMA(1) RECEPTOR-BINDING
    GLENNON, RA
    ABLORDEPPEY, SY
    ISMAIEL, AM
    ELASHMAWY, MB
    FISCHER, JB
    HOWIE, KB
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (08) : 1214 - 1219
1234