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Title
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Synthesis and antimicrobial activities of analogs and revision of the structure of ageloximes
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Author
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Abstract
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| (+)-N6-Hydroxyagelasine D, the enantiomer of the proposed structure of (−)-ageloxime D, as well as N6-hydroxyagelasine analogs were synthesized by selective N-7 alkylation of N6-[tert-butyl(dimethyl)silyloxy]-9-methyl-9H-purin-6-amine in order to install the terpenoid side chain, followed by fluoride mediated removal of the TBDMS-protecting group. N6-Hydroxyagelasine D and the analog carrying a geranylgeranyl side chain displayed profound antimicrobial activities against several pathogenic bacteria and protozoa and inhibited bacterial biofilm formation. However these compounds were also toxic towards mammalian fibroblast cells (MRC-5). The spectral data of N6-hydroxyagelasine D did not match those reported for ageloxime D before. Hence, a revised structure of ageloxime D was proposed. Basic hydrolysis of agelasine D gave (+)-N-[4-amino-6-(methylamino)pyrimidin-5-yl]-N-copalylformamide, a compound with spectral data in full agreement with those reported for (−)-ageloxime D. |
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Language
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English
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Source (journal)
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Bioorganic and medicinal chemistry. - Oxford
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Publication
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Oxford
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2019
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ISSN
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0968-0896
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DOI
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10.1016/J.BMC.2019.01.002
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Volume/pages
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27
:4
(2019)
, p. 620-629
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ISI
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000456835900004
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Pubmed ID
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30638761
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Full text (Publisher's DOI)
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Full text (open access)
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Full text (publisher's version - intranet only)
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