C-nucleoside analogues of furanfurin as ligands to A1 adenosine receptors.
Furanfurin (2-beta-D-ribofuranosylfuran-4-carboxamide) derivatives and analogues were synthesized and their affinity for adenosine receptors was determined. The agonistic behavior of furanfurin against A1 receptors is preserved only when the furan ring is substituted with isosteric pentatomic ring systems such as oxazole, thiazole or thiophene, and the carboxamide group is unsubstituted. Replacement of the hydrogen atoms of the carboxamide group with alkyl, cycloalkyl or arylalkyl groups generates compounds endowed with moderate antagonistic activity.
Franchetti
P
P
Dipartimento di Scienze Chimiche, Università di Camerino, Italy. frapa@camserv.unicam.it
Cappellacci
L
L
Marchetti
S
S
Martini
C
C
Costa
B
B
Varani
K
K
Borea
P A
PA
Grifantini
M
M
D000067956:Adenylyl Cyclase Inhibitors; D000262:Adenylyl Cyclases / Q000378:metabolism; D017667:Adipocytes / Q000201:enzymology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D001667:Binding, Competitive; D001792:Blood Platelets / Q000201:enzymology; D001921:Brain / Q000648:ultrastructure; D002417:Cattle; D020650:Combinatorial Chemistry Techniques; D006801:Humans; D020128:Inhibitory Concentration 50; D007700:Kinetics; D008024:Ligands; D008566:Membranes / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry / Q000494:pharmacology; D011485:Protein Binding; D051381:Rats; D018047:Receptors, Purinergic P1 / Q000378:metabolism*; D012254:Ribavirin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D012263:Ribonucleosides / Q000737:chemistry* / Q000494:pharmacology*; D012266:Ribose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000067956:Adenylyl Cyclase Inhibitors; D000970:Antineoplastic Agents; D008024:Ligands; D010080:Oxazoles; D018047:Receptors, Purinergic P1; D012263:Ribonucleosides; C095763:furanfurin; C065915:oxazofurin; D012254:Ribavirin; D012266:Ribose; D000262:Adenylyl Cyclases; C033706:tiazofurin