249509-38-4

Upstream product

• 78097-08-2 1-<(2-acetoxyethoxy)methyl>-5-iodouracil 
• 139416-71-0 1-(o-tolyl)prop-2-yn-1-ol 
• 1027588-01-7 Acetic acid 2-[5-(3-hydroxy-3-o-tolyl-prop-1-ynyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy]-ethyl ester 

Relevant academic research and scientific papers

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

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-(2hydroxyethoxy-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.

Unusual cytotoxicities of 5-(acylethynyl)-1-(2- hydroxyethoxy)methyluracils

5-(Acylethynyl)-1-(2-hydroxyethoxy)methyl uracils (2)-(6) were synthesised in excellent yields from 1-(2-acetoxyethoxy)methyl-5-iodouracil (7) utilising palladium-copper catalysed reactions. Compounds (2)-(5) were shown to be highly active against CCRF-CEM (IC50 0.6-1.6 μM) and L1210/0 cells (IC50 0.7-2.2 μM) in culture, and thus exhibit greater activity than their parent bases.