71171-58-9Relevant academic research and scientific papers
Rapid and selective reduction of amide group by borane-amine complexes in acyl protected nucleosides
Sergueeva, Zinaida A.,Sergueev, Dmitri S.,Shaw, Barbara Ramsay
, p. 275 - 282 (2000)
Borane-amine complexes provide an unusually fast and selective reduction of a deoxynucleoside N-acyl group to a corresponding N-alkyl group. Three different nucleosides (dG, dA, and dC) each having one of three N-protecting groups (benzoyl, isobutyryl, or acetyl) were used to prepare N-alkylated nucleosides in good yields under mild conditions. Deoxyribose O-acyl protecting groups remain intact at the conditions of N-acyl group reduction.
Synthesis of N2-modified 7-methylguanosine 5′- monophosphates as nematode translation inhibitors
Piecyk, Karolina,Davis, Richard E.,Jankowska-Anyszka, Marzena
experimental part, p. 4781 - 4789 (2012/08/29)
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.
Reactivity Effects on Site Selectivity in Nucleoside Aralkylation: A Model for the Factors Influencing the Sites of Carcinogen-Nucleic Acid Interactions
Moschel, Robert C.,Hudgins, W. Robert,Dipple, Anthony
, p. 4180 - 4185 (2007/10/02)
Product distributions are described for 15 reactions between guanosine (1) and a series of p-Y-benzyl bromides (2a-e), p-Y-benzoyl chlorides (3a-e), and N-nitroso-N-(p-Y-benzyl)ureas (4a-e) where Y = a, O2N; b, Cl; c, H; d, CH3; e, CH3O.The yields of products from reaction at the 7-position of guanosine to produce 7-(p-Y-benzyl)guanosines (5a-e), at N2 to produce N2-(p-Y-benzyl)guanosines (6a-e), at the O6-position to produce O6-(p-Y-benzyl)guanosines (7a-e), and at the 5-position to produce 4-(p-Y-benzyl)-5-guanidino-1-β-D-ribofuranosylimidazoles (8a-e) arecorrelated with the mechanism of the reaction (i.e., the SN2 or SN1 character) imposed by the para substituent and/or leaving group and the nature of the incipient charge density (i.e., the "hardness" or "softness") at the reaction center.These observations, coupled with the literature on sites of reaction of carcinogens with nucleic acid components, are used to rationalize the site selectivity differences exhibited by the alkylating and aralkylating classes of carcinogens in their nucleic acid reactions.
