Structureaactivity relationships of 2-arylamido-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxamide derivatives as cannabinoid receptor agonists and their analgesic action

Structureaactivity relationships of 2-arylamido-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxamide derivatives as cannabinoid receptor agonists and their analgesic action

SAR studies were performed on a series of 2-arylamido-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxamide derivatives as cannabinoid receptor agonists. Starting from a HTS hit both potency and selectivity could be improved. Modifications to the thiophene fusion and C-3 amides were studied. A representat...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2012-12, Vol.22 (24), p.7314-7321
Hauptverfasser: Thur, Yithachu, Bhalerao, Amit, Munshi, Zaki, Pansare, Nisha, Mann, Klaus, Hanauer, Guido, Kley, Hans-Peter, Nappe, Sandra, Weiss-Haljiti, Cornelia, Ostermann, Claude, Zitt, Christof, Schaefer, Michaela, Mondal, Dibyendu, Ali Siddiki, Afsar, Armugam, Velavan, Gudaghe, Vinod, Gupta, Mahendra, Rayudu, Pramila, Dautzenberg, Frank M, Das Sarma, Koushik
Format: Artikel
Sprache:eng
Schlagworte:
amides
Analgesia
Analgesics
Cannabinoid receptors
Inflammation
Pain perception
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Zusammenfassung:SAR studies were performed on a series of 2-arylamido-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxamide derivatives as cannabinoid receptor agonists. Starting from a HTS hit both potency and selectivity could be improved. Modifications to the thiophene fusion and C-3 amides were studied. A representative compound 3t produced analgesia when dosed orally in inflammatory pain models of writhing and carrageenan-induced allodynia.
ISSN:0960-894X
DOI:10.1016/j.bmcl.2012.10.087