title: Synthesis of N²-modified 7-methylguanosine 5'-monophosphates as nematode translation inhibitors.
abstract: Preparative scale synthesis of 14 new N(2)-modified mononucleotide 5' mRNA cap analogues was achieved. The key step involved use of an S(N)Ar 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 IC(50) ∼0.9μM was a N(2)-p-metoxybenzyl-7-methylguanosine-5'-monophosphate 35.
authors: Faculty of Chemistry, University of Warsaw, 02-093 Warsaw, Poland.
authors: Karolina
authors: K
authors: Piecyk
authors: Richard E
authors: RE
authors: Davis
authors: Marzena
authors: M
authors: Jankowska-Anyszka
mesh_terms: D000818:Animals; D017165:Ascaris suum / Q000196:embryology / Q000201:enzymology / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D049410:Luciferases, Renilla / Q000037:antagonists & inhibitors* / Q000378:metabolism; D015394:Molecular Structure; D011500:Protein Synthesis Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012314:RNA Cap Analogs / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012333:RNA, Messenger / Q000037:antagonists & inhibitors / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D011500:Protein Synthesis Inhibitors; D012314:RNA Cap Analogs; D012333:RNA, Messenger; C011925:7-methylguanosine-5'-monophosphate; D049410:Luciferases, Renilla