Design and synthesis of bioactive adamantane spiro heterocycles.


Kolocouris, N; Zoidis, G; Foscolos, GB; Fytas, G; Prathalingham, SR; Kelly, JM; Naesens, L; De Clercq, E; (2007) Design and synthesis of bioactive adamantane spiro heterocycles. Bioorganic & medicinal chemistry letters, 17 (15). pp. 4358-62. ISSN 0960-894X DOI: https://doi.org/10.1016/j.bmcl.2007.04.108

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Abstract

Spiro[aziridine-2,2'-adamantanes] 1 and 2, spiro[azetidine-2,2'-adamantanes] 3 and 5, spiro[azetidine-3,2'-adamantane] 13, spiro[piperidine-4,2'-adamantanes] 25 and 27, and spiro barbituric analog 18 were synthesized and tested for their anti-influenza A virus properties and for trypanocidal activity. The effect of ring size on potency was investigated. Piperidine 25 showed significant anti-influenza A virus activity, being 12-fold more active than amantadine, about 2-fold more active than rimantadine, and 54-fold more potent than ribavirin. It also proved to be the most active of the compounds tested against bloodstream forms of the African trypanosome, Trypanosoma brucei, being 1.5 times more potent than rimantadine and at least 25 times more active than amantadine.

Item Type: Article
Faculty and Department: Faculty of Infectious and Tropical Diseases > Dept of Pathogen Molecular Biology
PubMed ID: 17588747
Web of Science ID: 248462300053
URI: http://researchonline.lshtm.ac.uk/id/eprint/9429

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