Synthesis and antimicrobial activity of pyranobenzoquinones related to the pyranonaphthoquinone antibiotics.
The synthesis and antimicrobial activity of isochromane-type analogs of the pyranonaphthoquinone antibiotics are reported. Isochromane derivatives with (17a, b) and without (22a, b) a C-4 hydroxyl moiety and their corresponding quinones (19a and 23), were prepared. Both quinones exhibited antimicrobial activity against Staphylococcus aureus, Bacillus atrophaeus and Streptococcus agalactiae, while the related isochromanes were inactive. The results suggest that the quinone moiety is important for biological activity while the C-4 hydroxyl may not be essential.
Lagorio
S H
SH
Instituto de Química Orgánica de Síntesis (CONICET-UNR) and Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, Rosario, Argentina.
Bianchi
D A
DA
Sutich
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EG
Kaufman
T S
TS
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared
D000900:Anti-Bacterial Agents; D016227:Benzoquinones; D002839:Chromans