Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones.
Bioorg Med Chem Lett
; 14(3): 757-60, 2004 Feb 09.
Article
em En
| MEDLINE
| ID: mdl-14741284
ABSTRACT
The elaboration and biological activity of 15, containing the proposed pharmacophore for the antibiotic activity of the pyranonaphthoquinones, are reported. The synthetic strategy involved acid-catalyzed lactonization of mandelate 17 for isochroman ring formation, in combination with a Wittig-oxa-Michael functionalization of isochroman-3-ol derivative 20, a lactonization involving configurational inversion of a benzylic alcohol and a final AgO oxidation. Compound 15 showed activity against Staphylococcus aureus and Bacillus subtilis with MIC of 64 and 32 microg/mL, respectively.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Staphylococcus aureus
/
Bacillus subtilis
/
Naftoquinonas
/
Compostos Heterocíclicos
/
Antibacterianos
Idioma:
En
Ano de publicação:
2004
Tipo de documento:
Article