Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 6, Issue 17, Pages 3177-3185Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b804907f
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Funding
- State Scholarship Foundation of Greece
- Wellcome Trust
- Fonds voor Wetenschappelijk Onderzoek Vlaanderen [G.0188.07]
- International Consortium for Antivirals
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Adamantanopyrrolidines 8, 9 and 10, adamantanopyrrolidines 16 and 18, adamantanoxazolone 20, adamantanopyrazolone 23, adamantanopyrazolothione 24 and adamantanocyclopentanamine 32 were synthesized and tested for anti-influenza A virus and trypanocidal activity, The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. Pyrrolidine 16 proved to be the most active of the compounds tested against influenza A virus, being 4-fold more active than amantadine, equipotent to rimantadine and 19-fold more potent than ribavirin. Oxazolone 20 showed significant trypanocidal activity against bloodstream forms of the African trypanosome. Trypanosoma brucei, being approximately 3 times more potent than rimantadine and almost 50-fold more active than amantadine.
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