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Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions.

ABSTRACT: A series of 10,13-disubstituted 16-membered macrolides was synthesized using nitroso Diels-Alder reactions of leucomycin A7. Despite the extensive constituent functionalities in leucomycin, the hetero cycloaddition reactions proceeded in a highly regio- and stereoselective fashion. Subsequent chemical modifications of the nitroso cycloadducts, including N-O bond reduction, were also conducted. Most leucomycin derivatives retained antibiotic profiles similar to leucomycin A7, and, in contrast to leucomycin itself, several exhibited moderate antiproliferative and cytotoxic activity.

SUBMITTER: Yang B

PROVIDER: S-EPMC4058769 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions.

Yang Baiyuan B Zöllner Tina T Gebhardt Peter P Möllmann Ute U Miller Marvin J MJ

Organic & biomolecular chemistry 20091211 3

A series of 10,13-disubstituted 16-membered macrolides was synthesized using nitroso Diels-Alder reactions of leucomycin A7. Despite the extensive constituent functionalities in leucomycin, the hetero cycloaddition reactions proceeded in a highly regio- and stereoselective fashion. Subsequent chemical modifications of the nitroso cycloadducts, including N-O bond reduction, were also conducted. Most leucomycin derivatives retained antibiotic profiles similar to leucomycin A7, and, in contrast to ...[more]

PMID: 20090988

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