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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.

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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.

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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.