Synthesis and evaluation of imidazolidinones as nonpeptide HIV-protease inhibitors

Imidazolidinones were synthesized from 7-membered ring cyclic ureas via a sequential series of novel ring contraction reactions proceeding first through the tetrahydropyrimidinones and finally to the 5-membered ring heterocycle. These imidazolidinones are shown to be excellent HIV-PR inhibitors. The...

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Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 7; no. 5; pp. 495 - 500
Main Author De Lucca, George V.
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 04.03.1997
Elsevier
Subjects
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Biological and medical sciences
Medical sciences
Pharmacology. Drug treatments
Imidazole derivatives
Five membered ring
RNA-directed DNA polymerase
Enzyme
Nitrogen heterocycle
Transferases
Retroviridae
Enzyme inhibitor
Non peptide compound
In vitro
Virus
Peptidases
Nucleotidyltransferases
Structure activity relation
Amidoxime
Hydrolases
Lentivirinae
Antiviral
Ring contraction
Ureas
Human immunodeficiency virus
Chemical synthesis
Seven membered ring
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Summary:Imidazolidinones were synthesized from 7-membered ring cyclic ureas via a sequential series of novel ring contraction reactions proceeding first through the tetrahydropyrimidinones and finally to the 5-membered ring heterocycle. These imidazolidinones are shown to be excellent HIV-PR inhibitors. The most potent compound 20 having a K i = 17 nM. Imidazolidinones were synthesized from 7-membered ring cyclic ureas via a sequential series of novel ring contraction reactions proceeding first through the tetrahydropyrimidinones and finally to the 5-membered ring heterocycle. These imidazolinones are shown to be excellent HIV protease inhibitors.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(97)00006-1