69139-25-9Relevant academic research and scientific papers
Facile access to Fe(III)-complexing cyclic hydroxamic acids in a three-component format
Chupakhin, Evgeny,Bakulina, Olga,Dar’in, Dmitry,Krasavin, Mikhail
, (2019)
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.
One-pot synthesis and radical scavenging activity of novel polyhydroxylated 3-arylcoumarins
Svinyarov, Ivan,Bogdanov, Milen G.
, p. 198 - 206 (2014/04/17)
An unexpected domino rearrangement brought about the development of a novel one-pot procedure for synthesis of coumarins. This protocol allowed the gram-scale synthesis of a variety of polyhydroxylated derivatives 3a-p, from readily available starting materials at a low cost. Based on two proven intermediates, a probable mechanism consisting of boron tribromide induced demethylation/lactone ring opening/elimination/isomerization/lactone ring closure reaction sequence of in situ formed 3-aryl-3,4-dihydroisocoumarin-4- carboxylic acids was deduced. Compared to the common methods, used for the synthesis of coumarins, the proposed herein possesses great advantages, such as mild conditions, good yields for short reaction time, simple work-up procedure and easy isolation of the final products. The structure of the newly synthesized compounds 3a-p was established by spectroscopic methods (1H NMR, 13C NMR, IR, MS and HRMS) and their radical scavenging activity was evaluated in vitro against 1,1-diphenyl-2-picrylhydrazyl free radical (DPPH). The results obtained show that compounds 3g-p posses higher radical scavenging activity (3.16 SC;bsubesub[μM] ; 6.82) than well-known antioxidants such as trolox, protocatechuic acid, caffeic acid and gallic acid (SC50 [μM] = 9.34, 8.83, 9.48, 5.33, respectively), which is a precondition for promising antioxidant activity of these compounds to be expected.
