Fructose-fused γ-butyrolactones and lactams, synthesis and biological evaluation as GABA receptor ligands

被引：22
作者：
Araujo, Ana C. [2 ,3 ]
Nicotra, Francesco [1 ]
Costa, Barbara [1 ]
Giagnoni, Gabriella [1 ]
Cipolla, Laura [1 ]
机构：
[1] Univ Milano Bicocca, Dept Biosci & Biotechnol, I-20126 Milan, Italy
[2] Univ Lisbon, Dept Quim & Bioquim, P-1749016 Lisbon, Portugal
[3] CQB, P-1749016 Lisbon, Portugal
来源：
CARBOHYDRATE RESEARCH | 2008年 / 343卷 / 10-11期
关键词：
C-glycosides; fructose; gamma-butyrolactones; gamma-butyrolactams; GABA receptors;
D O I：
10.1016/j.carres.2008.03.013
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：
We describe the synthesis of sugar-fused beta-disubstituted gamma-butyrolactones, gamma-butyrolactams and a lipophilic beta-disubstituted GABA analogue as potential GABA receptor ligands, where the pharmacophore is engineered into the carbohydrate scaffold in the form of a C-fructoside. The products were characterized for receptor binding studies of GABA(A) receptors. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1840 / 1848
页数：9
相关论文
共 63 条
  • [1] The psychobiology of anxiolytic drugs - Part 2: pharmacological treatments of anxiety
    Argyropoulos, SV
    Sandford, JJ
    Nutt, DJ
    [J]. PHARMACOLOGY & THERAPEUTICS, 2000, 88 (03) : 213 - 227
  • [2] Anxioselective Compounds Acting at the GABAA Receptor Benzodiazepine Binding Site
    Atack, John R.
    [J]. CNS & NEUROLOGICAL DISORDERS-DRUG TARGETS, 2003, 2 (04) : 213 - 232
  • [3] The benzodiazepine binding site of GABAA receptors as a target for the development of novel anxiolytics
    Atack, JR
    [J]. EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2005, 14 (05) : 601 - 618
  • [4] PEPTIDES AND THE BLOOD-BRAIN-BARRIER - LIPOPHILICITY AS A PREDICTOR OF PERMEABILITY
    BANKS, WA
    KASTIN, AJ
    [J]. BRAIN RESEARCH BULLETIN, 1985, 15 (03) : 287 - 292
  • [5] What is GABAergic inhibition? How is it modified in epilepsy?
    Bernard, C
    Cossart, R
    Hirsch, JC
    Esclapez, M
    Ben-Ari, Y
    [J]. EPILEPSIA, 2000, 41 : S90 - S95
  • [6] Bryans JS, 1999, MED RES REV, V19, P149, DOI 10.1002/(SICI)1098-1128(199903)19:2<149::AID-MED3>3.0.CO
  • [7] 2-B
  • [8] Structure-activity studies of fluoroalkyl-substituted γ-butyrolactone and γ-thiobutyrolactone modulators of GABAA receptor function
    Canney, DJ
    Lu, HF
    McKeon, AC
    Yoon, KW
    Xu, K
    Holland, KD
    Rothman, SM
    Ferrendelli, JA
    Covey, DF
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (01) : 43 - 55
  • [9] The 'ABC' of GABA receptors: A brief review
    Chebib, M
    Johnston, GAR
    [J]. CLINICAL AND EXPERIMENTAL PHARMACOLOGY AND PHYSIOLOGY, 1999, 26 (11) : 937 - 940
  • [10] GABA-activated ligand gated ion channels: Medicinal chemistry and molecular biology
    Chebib, M
    Johnston, GAR
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (08) : 1427 - 1447
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