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New oleandomycin 9-oximes. Synthesis, characterization and biological activity
G Lazarevski1, G Kobrehel, S Dokić
1PLIV--Pharmaceutical, Chemical, Food and Cosmetic Industry, Research Institute, Zagreb, Croatia.
The Journal of Antibiotics
|March 1, 1994
Summary
Novel oleandomycin 9-oximes were synthesized and tested for antibacterial activity. The 8(R)-isomer derivative demonstrated significant in vitro potency, advancing to further studies.
Area of Science:
- Medicinal Chemistry
- Microbiology
- Organic Synthesis
Background:
- Oleandomycin is a macrolide antibiotic with established antibacterial properties.
- Modifications of existing antibiotics can lead to compounds with improved efficacy or altered pharmacokinetic profiles.
Purpose of the Study:
- To synthesize novel oleandomycin 9-oxime derivatives.
- To evaluate the in vitro antibacterial activity of these new compounds.
- To compare the activity of novel oximes with the parent oleandomycin.
Main Methods:
- Synthesis of oleandomycin 9-oximes.
- Characterization using spectroscopic data (e.g., NMR, Mass Spectrometry) and X-ray crystallography.
- In vitro antibacterial activity assays against relevant microbial strains.
Main Results:
- A series of novel oleandomycin 9-oximes were successfully prepared and characterized.
- 8(R)-methyloleandomycin-9-oxime (compound 9) exhibited the most potent in vitro antibacterial activity among the tested derivatives.
- The 8(S)-isomer (compound 10) showed significantly lower potency.
- Preliminary pharmacokinetic data for compound 9 supported its observed activity.
Conclusions:
- The synthesis of oleandomycin 9-oximes provides a new class of potential antibacterial agents.
- Stereochemistry at the 8-position is critical for antibacterial potency, with the (R)-configuration being superior.
- Compound 9 is a promising candidate for further investigation and development as an antibacterial drug.