Precursor-directed syntheses and biological evaluation of new elansolid derivatives.
The antibiotic elansolid C1 (8) was isolated from Chitinophaga sancti strain FxGBF13 after fermentation in the presence of anthranilic acid. Remarkably, 8 was also obtained by addition of anthranilic acid to a crude fermentation extract containing the macrolide elansolid A2 (1*). This Michael-type conjugate addition allowed us to generate 21 new derivatives of elansolid C1 (9-29) by using various nucleophiles. Biological activities of all derivatives were evaluated against Staphylococcus aureus, Micrococcus luteus, and the mouse cell line L929.
Helmholtz Centre for Infection Research, Research Group Microbial Drugs, Inhoffenstrasse 7, 38124 Braunschweig, Germany.
Heinrich
H
Steinmetz
Wiebke
W
Zander
Muftah A M
MA
Shushni
Rolf
R
Jansen
Klaus
K
Gerth
Richard
R
Dehn
Gerald
G
Dräger
Andreas
A
Kirschning
Rolf
R
Müller
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001419:Bacteria / Q000737:chemistry; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D045424:Complex Mixtures / Q000737:chemistry; D004353:Drug Evaluation, Preclinical; D005285:Fermentation; D005347:Fibroblasts / Q000187:drug effects*; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects* / Q000254:growth & development; D013211:Staphylococcus aureus / Q000187:drug effects* / Q000254:growth & development; D062367:ortho-Aminobenzoates / Q000737:chemistry
D000900:Anti-Bacterial Agents; D045424:Complex Mixtures; D018942:Macrolides; C576575:elansolid C1; D062367:ortho-Aminobenzoates; C031385:anthranilic acid