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Synthesis of a Non-Symmetrical Disorazole C1-Analogue and Its Biological Activity.

ABSTRACT: The synthesis of a novel disorazole C1 analogue is described, and its biological activity as a cytotoxic compound is reported. Based on our convergent and flexible route to the disorazole core, we wish to report a robust strategy to synthesize a non-symmetrical disorazole in which we couple one half of the molecule containing the naturally occurring oxazole heterocycle and the second half of the disorazole macrocycle containing a thiazole heterocycle. This resulted in a very unusual non-symmetrical disorazole C1 analogue containing two different heterocycles, and its biological activity was studied. This provided exciting information about SAR (structure-activity-relationship) for this highly potent class of antitumor compounds.

SUBMITTER: Lizzadro L 

PROVIDER: S-EPMC10934378 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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Synthesis of a Non-Symmetrical Disorazole C<sub>1</sub>-Analogue and Its Biological Activity.

Lizzadro Luca L   Spieß Oliver O   Reinecke Silke S   Stadler Marc M   Schinzer Dieter D  

Molecules (Basel, Switzerland) 20240301 5

The synthesis of a novel disorazole C<sub>1</sub> analogue is described, and its biological activity as a cytotoxic compound is reported. Based on our convergent and flexible route to the disorazole core, we wish to report a robust strategy to synthesize a non-symmetrical disorazole in which we couple one half of the molecule containing the naturally occurring oxazole heterocycle and the second half of the disorazole macrocycle containing a thiazole heterocycle. This resulted in a very unusual n  ...[more]

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