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Antibacterial Mimics of Natural Products by Side-Chain Functionalization of Bicyclic Tetramic Acids.
Josa-Culleré, Laia; Pretsch, Alexander; Pretsch, Dagmar; Moloney, Mark G.
Afiliación
  • Josa-Culleré L; Department of Chemistry, Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
  • Pretsch A; Oxford Antibiotic Group , The Oxford Science Park, Magdalen Centre , Oxford OX4 4GA , U.K.
  • Pretsch D; Oxford Antibiotic Group , The Oxford Science Park, Magdalen Centre , Oxford OX4 4GA , U.K.
  • Moloney MG; Department of Chemistry, Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.
J Org Chem ; 83(17): 10303-10317, 2018 09 07.
Article en En | MEDLINE | ID: mdl-30028145
Tetramic acids with unsaturated acyl chains are widely found in natural products possessing a range of biological activities, and bicyclic tetramates represent a suitable scaffold to prepare simple mimics of such complex molecules. An efficient route to functionalize the C(6)-acyl group of a bicyclic tetramate was developed and utilized to prepare a small chemical library with a range of saturated and unsaturated side-chains. The analogues with lipophilic residues possessed highly potent antibacterial activity, which was selective for Gram-positive bacteria, and the best compound was 37-fold more potent than the cephalosporin C control and with an appropriate therapeutic window.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Pirrolidinonas / Productos Biológicos / Materiales Biomiméticos / Antibacterianos Idioma: En Revista: J Org Chem Año: 2018 Tipo del documento: Article Pais de publicación: Estados Unidos
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Pirrolidinonas / Productos Biológicos / Materiales Biomiméticos / Antibacterianos Idioma: En Revista: J Org Chem Año: 2018 Tipo del documento: Article Pais de publicación: Estados Unidos