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-vinyland -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 (MoW4F and MT-4) versus murine (L1210 and FM3A) tumor cell lines.

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. © 1995, American Chemical Society. All rights reserved.

Synthesis and cytotoxic activity of 6-vinyl- and 6-ethynyluridine and 8-vinyl- and 8-ethynyladenosine

MANFREDINI, Stefano;BARALDI, Pier Giovanni;SIMONI, Daniele;
1995

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. © 1995, American Chemical Society. All rights reserved.
1995
Manfredini, Stefano; Baraldi, Pier Giovanni; Bazzanini, Rita; Marangoni, Mirella; Simoni, Daniele; Balzarini, Jan; DE CLERCQ, Erik
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/460430
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