Premium
Synthesis and anti‐HIV activity of HEPT and S‐DABO‐analogues with 5‐Benzyl and 5‐Phenyl substituents
Author(s) -
Larsen Janus S.,
Aal Mohammed Taha Abdel,
Pedersen Erik B.,
Nielsen Claus
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380323
Subject(s) - chemistry , alkylation , acetone , human immunodeficiency virus (hiv) , sulfur , yield (engineering) , stereochemistry , organic chemistry , catalysis , virology , materials science , metallurgy , biology
6‐Benzyl‐5‐phenyluracil (4) and 5,6‐dibenzyluracil (9) were synthesised from diphenyl acetone (1) and ethyl 3‐oxo‐4‐phenylbutyrate (6) , respectively. The uracils were alkylated to afford the 1‐alkoxymethyl‐uracils 5, 10 and 11 . Furthermore, S‐alkylated dihydroalkoxybenzyloxopyrimidine (S‐DABO) analogues were prepared by alkylating 5,6‐dibenzyl‐2‐thiouracil (8) on sulfur to yield compounds 12a ‐f. All compounds were tested for their inhibition of HIV‐1 reverse transcriptase, and moderate activity was found for 6‐benzyl‐1‐(ethoxymethyl)‐5‐phenyluracil (5) .