ISSN:
1434-193X
Keywords:
Nucleosides
;
Acyclic analogues
;
Purines
;
Alkylations
;
15N NMR
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
N7- and N9-regioisomers of cyanomethyl and trifluoroethyl-N6-[(dimethylamino)methylene]adenine (1, 2, 6, 7) were prepared regioselectively, the former by the direct alkylation of N6-[(dimethylamino)methylene]adenine, the latter by the alkylation of adenine followed by protection of the amino group. These derivatives, which bear an active methylene group, were submitted to reactions with allyl bromide, aldehydes or tert-butoxybis(dimethylamino)methane in order to modify their side chain. In this way, several new α-branched acyclic adenosine analogues (8, 10-16) were prepared; the regioselectivity of the alkylation and the product structures were determined by 1H- and 13C-NMR spectroscopy. 15N-NMR parameters for selected compounds were studied by gradient-enhanced inverse-detected techniques. In addition, X-ray data of derivatives 1, 2 and 7 are reported.Supporting information for this article is available on the WWW under /http://www.wiley-vch.de/contents/jc_2046/1999/99113_s.pdf or from the author.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
