GABA analogues derived from 4-aminocyclopent-1-enecarboxylic acid

Neurochemical Research

Volumn 34, Issue 10, 2009, Pages 1698-1703

  Locock, Katherine E S ^a   Johnston, Graham A R ^a   Allan, Robin D ^a  

^a University of Sydney   (Australia)

Author keywords

1 2 2L GABAA receptors; Antagonist; GABA analogues; Michael addition reaction; Oocytes; Receptor cavity; Thioethers

Indexed keywords

4 AMINO 2 (4 METHYLPHENYLTHIO)CYCLOPENTANECARBOXYLIC ACID; 4 AMINO 2 BENZYLTHIOCYCLOPENTANECARBOXYLIC ACID; 4 AMINO 2 PENTYLTHIOCYCLOPENTANECARBOXYLIC ACID; 4 AMINO 2 PROPYLTHIOCYCLOPENTANECARBOXYLIC ACID; 4 AMINOBUTYRIC ACID A RECEPTOR; 4 AMINOBUTYRIC ACID DERIVATIVE; 4 AMINOCYCLOPENT 1 ENECARBOXYLIC ACID; AMINO ACID; SULFIDE; UNCLASSIFIED DRUG;

ALPHA CHAIN; ANIMAL CELL; ARTICLE; BETA CHAIN; CHEMICAL REACTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; IC 50; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY; VOLTAGE CLAMP;

AMINO ACIDS, CYCLIC; ANIMALS; CYCLOHEXANECARBOXYLIC ACIDS; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; GAMMA-AMINOBUTYRIC ACID; HUMANS; RECEPTORS, GABA; RECEPTORS, GABA-A; RECEPTORS, GABA-B; STRUCTURE-ACTIVITY RELATIONSHIP; XENOPUS LAEVIS;

EID: 69049101035     PISSN: 03643190     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11064-009-0005-x     Document Type: Article

References (11)

1. A receptors and GABA uptake Eur J Pharmacol 122 339 348 10.1016/0014-2999(86) 90414-0
2. A agonists and partial agonists Chem Rec 2 419 430 10.1002/tcr.10040
3. A antagonists: synthesis, pharmacology and structure-activity relationships J Med Chem 50 1988 1992 10.1021/jm070038n
4. RD Allan J Fong 1986 Synthesis of analogues of GABA. XV. Preparation and resolution of some potent cyclopentene and cyclopentane derivatives Aust J Chem 39 855 864
5. C receptors Eur J Pharmacol 430 185 192 10.1016/S0014-2999(01)01390-5
6. GAR Johnston DR Curtis CJA Game RM McCulloch B Twitchin 1976 cis- and trans-3-aminocyclopentane-1-carboxylic acid as GABA analogues of restricted conformation Proc Aust Physiol Pharmacol Soc 7 32
7. H Abdel-Halim JR Hanrahan DE Hibbs GAR Johnston M Chebib 2008 A molecular basis for agonist and antagonist actions at GABA-C receptors Chem Biol Drug Des 71 306 327 10.1111/j.1747-0285.2008.00642.x
8. K Nishimura M Ono Y Nagaoka K Tomioka 1997 Steric tuning of reactivity and enantioselectivity in addition of thiophenol to enoates catalyzed by an external chiral ligand J Am Chem Soc 119 12974 12975 10.1021/ja9729950
9. SN Crane WC Black JT Palmer DE Davis E Setti J Robichaud J Paquet RM Oballa CI Bayly DJ McKay JR Somoza N Chauret C Seto J Scheigetz G Wesolowski F Masse S Desmarais M Ouellet 2006 Beta-substituted cyclohexanecarboxamide: a nonpeptidic framework for the design of potent inhibitors of cathepsin K J Med Chem 49 1066 1079 10.1021/jm051059p
10. AJ Cocuzsa GA Boawell 1985 Cyclobutanone analogues of beta-lactam antibiotics: synthesis of N-acetyldeazathienamycin Tetrahedron Lett 26 44 5363 5366 10.1016/S0040-4039(00)98208-X
11. RJ Kumar M Chebib DE Hibbs H-L Kim GAR Johnston NK Salam JR Hanrahan 2008 Novel gamma-aminobutyric acid rho1 receptor antagonists; synthesis, pharmacological activity and structure activity relationships J Med Chem 51 3825 3840 10.1021/jm7015842