Document Report Card

ID: ALA1128337

Journal: J Med Chem

Title: Synthesis and cytotoxic activity of 6-vinyl- and 6-ethynyluridine and 8-vinyl-and 8-ethynyladenosine.

Authors: Manfredini S, Baraldi PG, Bazzanini R, Marangoni M, Simoni D, Balzarini J, De Clercq E.

Abstract: It is well-known that the introduction of vinyl and ethynyl moieties into nucleosides is of crucial importance for cytostatic, antiviral, or other biological activities. In this study 6- and 8-vinyl-and -ethynyluridine and -adenosine were prepared by a general procedure involving the palladium-catalyzed cross-coupling of trimethylsilylacetylene or vinyltributyltin. The introduction of a vinyl group at C-6 of uridine or an ethynyl group at C-8 of adenosine resulted in nucleoside derivatives showing cytostatic activity against several murine and/or human tumor cell lines. Interestingly, 8-vinyladenosine had pronounced selective inhibitory effects on human (Molt/4F and MT-4) versus murine (L1210 and FM3A) tumor cell lines.

CiteXplore: 7837231

DOI: 10.1021/jm00001a025