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- Title
Facile Access to Fe(III)-Complexing Cyclic Hydroxamic Acids in a Three-Component Format.
- Authors
Chupakhin, Evgeny; Bakulina, Olga; Dar'in, Dmitry; Krasavin, Mikhail; Bunce, Richard A.; Belmont, Philippe; Dehaen, Wim; Babaev, Eugene
- Abstract
Cyclic hydroxamic acids can be viewed as effective binders of soluble iron and can therefore be useful moieties for employing in compounds to treat iron overload disease. Alternatively, they are analogs of bacterial siderophores (iron-scavenging metabolites) and can find utility in designing antibiotic constructs for targeted delivery. An earlier described three-component variant of the Castagnoli—Cushman reaction of homophthalic acid (via in situ cyclodehydration to the respective anhydride) was extended to involve hydroxylamine in lieu of the amine component of the reaction. Using hydroxylamine acetate and O-benzylhydroxylamine was key to the success of this transformation due to greater solubility of the reagents in refluxing toluene (compared to hydrochloride salt). The developed protocol was found suitable for multigram-scale syntheses of N-hydroxy- and N-(benzyloxy)tetrahydroisoquinolonic acids. The cyclic hydroxamic acids synthesized in the newly developed format have been tested and shown to be efficient ligands for Fe3+, which makes them suitable candidates for the above-mentioned applications.
- Subjects
HYDROXAMIC acids; COMPLEXATION reactions; IRON compounds; HYDROXYLAMINE; AZEOTROPIC distillation
- Publication
Molecules, 2019, Vol 24, Issue 5, p864
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules24050864