5-Substituted 2-aminothiophenes as A1 adenosine receptor allosteric enhancers

Bioorg Med Chem. 2008 Feb 1;16(3):1319-27. doi: 10.1016/j.bmc.2007.10.065.

Luigi Aurelio ¹, Heidi Figler, Bernard L Flynn, Joel Linden, Peter J Scammells

Affiliations

Affiliation

1 Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville VIC 3052, Australia.

PMID: 17980606 DOI: 10.1016/j.bmc.2007.10.065

Abstract

Two series of 5-substituted 2-amino-4-(3-trifluoromethylphenyl)thiophenes were prepared and evaluated as allosteric enhancers at the A(1) Adenosine Receptor (A(1)AR). In the 3-benzoyl series, a 5-phenyl group was found to confer the greatest potency (9a: ED(50)=2.1 microM, AE score=18%). However, the analogue with no 5-substituent (6b: ED(50)=15.8 microM, AE score=77%) proved to be the most efficacious. In the 3-ethoxycarbonyl series, the 5-(4-chlorophenyl) analogue was clearly the most potent and efficacious (9l: ED(50)=6.6 microM, AE score=57%). The antagonist activity of all compounds was measured using a [(3)H]CPX competitive binding assay.

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