New type of interaction of 5-iodopyrimidine nucleosides with alkynes

Searching for anti-glioma activity. Ribonucleoside analogues with modifications in nucleobase and sugar moieties.

“…Specifically, 7-(β-dribofuranosyl)adenine (2) and 1-(β-d-ribofuranosyl) adenine (7) were obtained as kinetic products in the ribosylation of adenine (Framski et al, 2006); 6-methyl-9-(β-d-ribofuranosyl)purine (4) and 7-(β-d-ribofuranosyl) guanine (5), via transglycosylation of inosine (Boryski, 1998) and guanosine (Boryski, 2008), respectively; 1-(β-ribofuranosyl)indazole (8) and 2-(β-d-ribofuranosyl) indazole (9) via direct ribosylation of indazole (Boryski, 1995); 5-azacytidine (11), via coupling of the silylated 5-azacytosine with peracetylated ribofuranose accord-ing to the Vorbrüggen method (Vorbrüggen & Bennua, 1978); 1-(β-d-ribofuranosyl)cyanuric acid (12), from silylated cyanuric acid and 1-O-acetyl-2,3,5-tri-O-benzoyld-ribofuranose (Khaled et al, 2004); 6-methyluridine (13), by Lewis acid catalyzed condensation of a silylated 6-methyl-4-methylthiouracyl with suitably protected ribofuranose (Felczak et al, 1996); 2'-C-β-methyl-d-cytidine (14), 5-aza-2'-C-β-methyl-d-cytidine (15), 5-fluoro-2'-Cβ-methyl-d-cytidine (16), and 2'-C-β-methyl-d-guanosine (17), were obtained by ribosylation of cytosine, its analogues, or guanine with 1,2,3,5-tetra-O-benzoyl-2'-Cmethyl-β-d-ribofuranose (Fogt et al, 2008). The series of furano[2,3-d]pyrimidine ribonucleoside derivatives (18, 19, and 20) were synthesized by the Pd-catalyzed crosscoupling of 5-iodouridine with appropriate alkyne derivatives (Jahnz-Wechmann et al, 2015;McGuigan et al, 2001;Tolstikov et al, 1993), and the pyrollo[2,3-d]pyrimidine ribonucleoside derivatives (21-26), by the ammonia treatment of the corresponding furanopyrimidine nucleoside precursors (Diez-Torrubia et al, 2011;Januszczyk et al, 2009) Biological assays. Cell line and culture conditions.…”