Palladium-catalyzed synthesis of [E]-6-(2-acylvinyl)uracils and [E]-6-(2-acylvinyl)-1-[(2-hydroxyethoxy)methyl]uracils--their antiviral and cytotoxic activities.
[E]-6-(2-Acylvinyl)uracils and their corresponding 1-(2-hydroxyethoxy)methyl derivatives were synthesized through palladium-catalyzed reactions which involved an interesting rearrangement. Some of the acylvinyl uracils (3, 4, and 5) and the acyclonucleosides (8 and 10) showed pronounced activity against human T-lymphocyte Molt 4/C8 and CEM cells. However, they were less toxic to murine L1210 and FM3A cells. The compounds did not have any marked antiviral activity.
Kundu
N G
NG
Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta. ocngk@iacs.ernet.in
Das
P
P
Balzarini
J
J
De Clercq
E
E
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D002384:Catalysis; D006801:Humans; D007939:Leukemia L1210 / Q000188:drug therapy; D008325:Mammary Neoplasms, Experimental / Q000188:drug therapy; D051379:Mice; D010165:Palladium / Q000737:chemistry*; D014407:Tumor Cells, Cultured; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D014498:Uracil; D010165:Palladium