Chemical and biological properties of 5-indolones.
Indolones of the general formula 1 (Fig. 1 and 2) can act as Michael substrates, which readily add various nucleophiles. 1,4-Addition of S-nucleophiles to these indolones gives access to compounds of the general formula 2 (Fig. 2). The addition is reversible, meaning that these compounds behave as prodrugs of the (in-vitro) cytotoxic indolones. The addition products possess less cytotoxicity of their own, but can presumably release the parent indolones in-vivo. This behaviour makes them valuable compounds, allowing their use as cytotoxic agents. Furthermore, some of the addition products possess antibiotic activity, making them worth testing as agents against certain microbes. Their specificity towards certain microorganisms, which does not fit the usual scheme of activity towards gram positive or gram negative bacteria, is remarkable and needs further verification.
Weber
W
W
Institut für Pharmazie, Universität Leipzig, Germany.
Habermann
A
A
Maisch
C C
CC
Eger
K
K
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D008826:Microbial Sensitivity Tests; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D007211:Indoles; D011355:Prodrugs