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Synthesis and anti-HIV activity of HEPT and S-DABO-analogues with 5-Benzyl and 5-Phenyl substituents

✍ Scribed by Janus S. Larsen; Mohammed Taha Abdel Aal; Erik B. Pedersen; Claus Nielsen

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
57 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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).

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