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3- and 6-Substituted 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines as A1 adenosine receptor allosteric modulators and antagonists.

Abstract：

:A series of 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines were prepared and evaluated as potential allosteric modulators at the A(1) adenosine receptor. The structure-activity relationships of the 3- and 6-positions of a series of 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines were explored. Despite finding that 3- and 6-substituted 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines possess the ability to recognize an allosteric site on the agonist-occupied A(1)AR at relatively high concentrations, the structural modifications we have performed on this scaffold favor the expression of orthosteric antagonist properties over allosteric properties. This research has identified 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines as novel class of orthosteric antagonist of the A(1)AR and highlighted the close relationship between structural elements governing allosteric modulation and orthosteric antagonism of agonist function at the A(1)AR.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Aurelio L,Valant C,Figler H,Flynn BL,Linden J,Sexton PM,Christopoulos A,Scammells PJ

doi

10.1016/j.bmc.2009.08.024

subject

Has Abstract

pub_date

2009-10-15 00:00:00

pages

7353-61

issue

20

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(09)00796-2

journal_volume

17

pub_type

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