Synthesis of N2-modified 7-methylguanosine 5′-monophosphates as nematode translation inhibitors

Preparative scale synthesis of 14 new N-2-modified mononucleotide 5' mRNA cap analogues was achieved. The key step involved use of an SNAr reaction with protected 2-fluoro inosine and various primary and secondary amines. The derivatives were tested in a parasitic nematode, Ascaris suum, cell-free system as translation inhibitors. The most effective compound with IC50 similar to 0.9 mu M was a N-2-p-metoxybenzyl-7-methylguanosine-5'-monophosphate 35. (C) 2012 Elsevier Ltd. All rights reserved.