Synthesis of new nebularine analogues and their inhibitory activity against adenosine deaminase.
A number of new 2,6-disubstituted-1-deazanebularine analogues as well as two structurally related pyrazole-fused tricyclic nucleosides were prepared. Their synthesis was carried out by the conversion of 6-amino-2-picoline to a suitable 1-deazapurine, followed by a Vorbrüggen type glycosylation and subsequent elaboration of the condensed pyrazole ring. The synthesized nebularine analogues proved to be weak adenosine deaminase inhibitors.
School of Health Sciences, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens.
Nikolaos
N
Lougiakis
Panagiotis
P
Marakos
Nicole
N
Pouli
Elisabeth
E
Fragopoulou
Roxane
R
Tenta
D000243:Adenosine Deaminase / Q000737:chemistry* / Q000378:metabolism; D058892:Adenosine Deaminase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D002417:Cattle; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D011485:Protein Binding; D011684:Purine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D011720:Pyrazoles / Q000737:chemistry; D012263:Ribonucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism
D058892:Adenosine Deaminase Inhibitors; D011684:Purine Nucleosides; D011720:Pyrazoles; D012263:Ribonucleosides; C031280:pyrazole; C005248:nebularine; D000243:Adenosine Deaminase