Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones

Darío A Bianchi; Emma G Sutich; Teodoro S Kaufman

doi:10.1016/j.bmcl.2003.11.015

Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones

Bioorg Med Chem Lett. 2004 Feb 9;14(3):757-60. doi: 10.1016/j.bmcl.2003.11.015.

Authors

Darío A Bianchi¹, Emma G Sutich, Teodoro S Kaufman

Affiliation

¹ Instituto de Química Orgánica de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, República, Suipacha 531, S2002LRK Rosario, Argentina.

PMID: 14741284
DOI: 10.1016/j.bmcl.2003.11.015

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / pharmacology*
Bacillus subtilis / drug effects*
Heterocyclic Compounds / chemistry*
Microbial Sensitivity Tests
Molecular Structure
Naphthoquinones / chemical synthesis*
Naphthoquinones / pharmacology*
Staphylococcus aureus / drug effects*
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Heterocyclic Compounds
Naphthoquinones