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Streptonigrin and lavendamycin partial structures. Preparation of 7‐amino‐2‐(2′‐pyridyl)quinoline‐5,8‐quinone‐6′‐carboxylic acid: A probe for the minimum, potent pharmacophore of the naturally occurring antitumor‐antibiotics
Author(s) -
Yasuda Masami,
Boger Dale L.
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240504
Subject(s) - chemistry , pharmacophore , quinoline , quinone , carboxylic acid , antimicrobial , stereochemistry , combinatorial chemistry , ring (chemistry) , antibiotics , organic chemistry , biochemistry
The preparation of 7‐amino‐2‐(2′‐pyridyl)quinoline‐5,8‐quinone‐6′‐carboxylic acid (4) constituting a potential minimum, potent pharmacophore of streptonigrin (1) and lavendamycin (2) , two structurally‐related naturally‐occurring antitumor‐antibiotic, is detailed. In contrast to observations associated with streptonigrin and lavendamycin in which the C‐6′ acid potentiates the antitumor, antimicrobial, and cytotoxic activity of the naturally‐occurring, substituted 7‐aminoquinoline‐5,8‐quinone AB ring systems, the C‐6′ carboxylic acid of 4 diminishes the observed antimicrobial and cytotoxic properties of 7‐amino‐2‐(2′‐pyridyl)quinoline‐5,8‐quinone.