SYNTHESIS AND CYTOTOXIC ACTIVITY OF 6-VINYLURIDINE AND 6-ETHYNYLURIDINE AND 8-VINYLADENOSINE AND 8-ETHYNYLADENOSINE

被引:62
作者
MANFREDINI, S [1 ]
BARALDI, PG [1 ]
BAZZANINI, R [1 ]
MARANGONI, M [1 ]
SIMONI, D [1 ]
BALZARINI, J [1 ]
DECLERCQ, E [1 ]
机构
[1] CATHOLIC UNIV LEUVEN,REGA INST,B-3000 LOUVAIN,BELGIUM
关键词
D O I
10.1021/jm00001a025
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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.
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页码:199 / 203
页数:5
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