53458-40-5Relevant academic research and scientific papers
Evaluation of the quantitative contribution of an aryl group on C(2) of 8-azaadenines to binding with adenosine deaminase: A new synthesis of 8-azaadenosine. XI
Biagi,Giorgi,Livi,Scartoni,Lucacchini
, p. 1457 - 1476 (2007/10/02)
The introduction of a phenyl group on C(2) of 8-azaadenosine increases binding to the adenosine deaminase enzyme (ADA). This stability increment has been quantitatively evaluated in both 8-azaadenosines and 9-(2',3'-dihydroxypropyl)-8-azaadenines; it resulted nearly equivalent in the two series. 8-Azaadenosine has been synthesized through a new route employing fully protected β-D-ribofuranosyl-1-azide. Instead, the stability difference in 9-(n-alkyl)-8-azaadenines, owing to the inactivity of the C(2) unsubstituted compounds, could not be evaluated. Consideration of the enantioselectivity of the ADA enzyme toward chiral 9-(2',3'-dihydroxypropyl)-8-azaadenines and 9-(2',3'-dihydroxypropyl)-8-azahypoxanthines allowed the exclusion of an appreciable structural modification in the enzyme-inhibitor complex when hydrogen on C(2) is substituted by an aryl group.
Synthesis and Biological Evaluation of 2-Fluoro-8-azaadenosine and Related Compounds
Montgomery, John A.,Shortnacy, Anita T.,Secrist, John A.
, p. 1483 - 1489 (2007/10/02)
The synthesis of 2-fluoro-8-azaadenosine (6e) and 2-amino-8-azaadenosine (6d) is described.Condensation of 9H-2,6-bis(methylthio)-8-azapurine (4) with 2,3,5-tri-O-acetyl-D-ribofuranosyl chloride (5) produces a mixture of 6a (9-β-D-ribofuranosyl) and 7a (8-β-D-ribofuranosyl).Standard functional group manipulation, including a modified Schiemann reaction to introduce the fluorine, allows preparation of 6d and 6e from the major isomer 6a.By a similar series of reactions the minor component 7a was converted to 7d and 7e, with the ribose ring attached at N-8 of the 8-azapurine ring system.Structure proofs utilized UV and 1H and 13C NMR data.Compounds 6b-e,g and 7b-f were evaluated in the H.Ep.-2 cell culture screen, and compounds 6c-e and 7d were evaluated in the P388 mouse leukemia screen.Adenosine deaminase data are also presented for some compounds.
