Investigation of the Anti-Methicillin-Resistant Staphylococcus aureus Activity of (+)-Tanikolide- and (+)-Malyngolide-Based Analogues Prepared by Asymmetric Synthesis |
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| Authors: | Joseph Breheny,Cian Kingston,Robert Doran,Joao Anes,Marta Martins,Sé amus Fanning,Patrick J. Guiry |
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| Affiliation: | 1.Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin D04 N2E5, Ireland; (J.B.); (R.D.);2.Synthesis and Solid State Pharmaceutical Centre, School of Chemistry, University College Dublin, Belfield, Dublin D04 N2E5, Ireland;3.UCD-Centre for Food Safety, University College Dublin, Belfield, Dublin D04 N2E5, Ireland; (J.A.); (M.M.); (S.F.) |
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| Abstract: | Herein, we report antibacterial and antifungal evaluation of a series of previously prepared (+)-tanikolide analogues. One analogue, (4S,6S)-4-methyltanikolide, displayed promising anti-methicillin-resistant Staphylococcus aureus activity with a MIC of 12.5 µg/mL. Based on the antimicrobial properties of the structurally related (−)-malyngolide, two further analogues (4S,6S)-4-methylmalyngolide and (4R,6S)-4-methylmalyngolide bearing a shortened n-nonyl alkyl side chain were prepared in the present study using a ZrCl4-catalysed deprotection/cyclisation as the key step in their asymmetric synthesis. When these were tested for activity against anti-methicillin-resistant Staphylococcus aureus, the MIC increased to 50 µg/mL. |
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| Keywords: | (+)-tanikolide, (− )-malyngolide, asymmetric synthesis, anti-methicillin-resistant Staphylococcus aureus activity |
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