1,3,4-Oxadiazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 2: SAR of the C5 position

1,3,4-Oxadiazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 2: SAR of the C5 position

The use of a 1,3,4-oxadiazole in combination with an 8-hydroxy-1,6-naphthyridine ring system has been shown to deliver potent enzyme and antiviral activity through inhibition of viral DNA integration. This report presents a detailed structure–activity investigation of the C5 position resulting in lo...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2009-03, Vol.19 (6), p.1807-1810
Hauptverfasser: Johns, Brian A., Weatherhead, Jason G., Allen, Scott H., Thompson, James B., Garvey, Edward P., Foster, Scott A., Jeffrey, Jerry L., Miller, Wayne H.
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acid Motifs
Anti-HIV Agents - chemical synthesis
Anti-HIV Agents - pharmacology
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Biological and medical sciences
Chelating Agents - pharmacology
Chemistry, Pharmaceutical - methods
Drug Design
HIV Infections - drug therapy
HIV Integrase Inhibitors - chemical synthesis
HIV Integrase Inhibitors - pharmacology
HIV-1 integrase
Human immunodeficiency virus 1
Humans
Integration
Medical sciences
Metals - chemistry
Models, Chemical
Molecular Structure
Naphthyridines - chemical synthesis
Naphthyridines - pharmacology
Oxadiazoles - chemistry
Pharmacology. Drug treatments
Structure-Activity Relationship
Triazoles - chemistry
Two-metal chelation
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Zusammenfassung:The use of a 1,3,4-oxadiazole in combination with an 8-hydroxy-1,6-naphthyridine ring system has been shown to deliver potent enzyme and antiviral activity through inhibition of viral DNA integration. This report presents a detailed structure–activity investigation of the C5 position resulting in low nM potency for several analogs with an excellent therapeutic index.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2009.01.089