5-(Acylethynyl)uracils, 5-(Acylethynyl)-2'-deoxyuridines and 5-(Acylethynyl)-1-(2-hydroxyethoxy)methyluracils. Their synthesis, antiviral and cytotoxic activities1

Add time:08/13/2019    Source:sciencedirect.com

5-(acylethynyl)uracils 4 were synthesized from 5-iodo-2,4-dimethoxypyrimidine 1 through a palladium-catalyzed reaction with acetylenic carbinols 5, subsequent oxidation with manganese dioxide in dichloromethane, demethylation with 6 N hydrochloric acid, followed by treatment with sodium hydroxide in 95% ethanol. The corresponding 5-acylethynyl-2'-deoxyuridines 9 and 5-acylethynyl-1-(2-hydroxyethoxy-methyl)uracils 13 were synthesized following a similar procedure. The 5-acylethynyluracils 4 were cytotoxic against murine L1210 and human T-lymphocyte (Molt 4/C8, CEM) cells. The 2'-deoxyuridine derivatives 9 were less cytotoxic; however the acyclonucleosides 13 were as active as the free bases 4. The compounds did not have antiviral activities at subtoxic concentrations.

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