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

Preparative scale synthesis of 14 new N2-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 ∼0.9 μM was a N2-p-metoxybenzyl-7-methylguanosine-5′-monophosphate 35.

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