28485-19-0Relevant articles and documents
Novel 5-(N -alkylaminouracil) acyclic nucleosides
Boncel, Sawomir,Gondela, Andrzej,McZka, MacIej,Tuszkiewicz-Kuznik, Magdalena,Grec, Przemysaw,Hefczyc, Barbara,Walczak, Krzysztof
experimental part, p. 603 - 610 (2011/04/12)
Protocols for the two-step syntheses of new 5-(N-hydroxyalkyl- and 5-N-benzylamino)uracil acyclic nucleosides bearing various functional groups (alkoxy/hydroxy and cyano/ester) are presented. Two groups of the title compounds were synthesised via aminolysis of 5-bromouracil and, subsequently, either coupling with an alkylating agent (2-chloromethoxyethyl acetate), or Michael-type addition to acrylonitrile/methyl acrylate. The reverse sequences for both syntheses were also studied. The target molecules were designed as non-nucleoside reverse transcriptase inhibitors (NNRTI) and are analogues of 1-(hydroxyethoxymethyl)-6-thiophenylthymine (HEPT) and 3-benzyl-1- cyanomethyluracils. The obtained compounds will be used in screening tests for anti-HIV-1 activity. Georg Thieme Verlag Stuttgart New York.
Synthesis of substituted uracils by the reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles under focused microwave irradiation
Fang, Woei-Ping,Cheng, Yuh-Tsyr,Cheng, Yann-Ru,Cherng, Yie-Jia
, p. 3107 - 3113 (2007/10/03)
Under microwave irradiation, the nucleophilic substitution reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to th
Synthesis of 1-(aryloxyalkyl)-5-(arylamino)uracils
Ozerov,Novikov,Brel',Solodunova
, p. 611 - 616 (2007/10/03)
In an attempt to obtain new non-nucleoside inhibitors of the reverse transcriptase HIV-1, we have carried out the synthesis of 1-(benzyloxymethyl)- and 1-[2-(4-R-phenoxy)ethyl]-5-(arylamino)uracils. Indirect alkylation of trimethylsilyl derivatives of 5-(arylamino)uracils with benzyl chloromethyl ether by the Gilbert-Jones method did not affect the exocyclic amino group and gave the corresponding 1-(benzyloxymethyl) derivatives in 58-74% yield. Alkylation of 5-(arylamino)uracils with 1-bromo-2-(4-R-phenoxy)ethane in anhydrous DMF in the presence of potassium carbonate gave a mixture of N1-mono- and N1,N1-disubstituted products with an overall yield of 46-55%. 1998 Plenum Publishing Corporation.