Facile access to Fe(III)-complexing cyclic hydroxamic acids in a three-component format

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Facile access to Fe(III)-complexing cyclic hydroxamic acids in a three-component format. / Chupakhin, Evgeny; Bakulina, Olga ; Dar’in, Dmitry ; Krasavin, Mikhail.

In: Molecules, Vol. 24, No. 5, 864, 01.03.2019.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{830fb0d5994c47cc8db4d45945f94de2,

title = "Facile access to Fe(III)-complexing cyclic hydroxamic acids in a three-component format",

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 Fe 3+ , which makes them suitable candidates for the above-mentioned applications. ",

keywords = "Azeotropic distillation, Castagnoli–Cushman reaction, Cyclic hydroxamic acids, Cyclodehydration, Homophthalic acid, Hydroxylamine acetate, Iron complexation, Siderophores/chemistry, Hydroxamic Acids/chemistry, Coordination Complexes/chemical synthesis, Ferric Compounds/chemical synthesis, BACTERIAL SIDEROPHORES, ANALOGS, ONE-POT SYNTHESIS, cyclodehydration, cyclic hydroxamic acids, hydroxylamine acetate, homophthalic acid, Castagnoli-Cushman reaction, azeotropic distillation, iron complexation, CHEMISTRY, CASTAGNOLI-CUSHMAN REACTION",

author = "Evgeny Chupakhin and Olga Bakulina and Dmitry Dar{\textquoteright}in and Mikhail Krasavin",

year = "2019",

month = mar,

day = "1",

doi = "10.3390/molecules24050864",

language = "English",

volume = "24",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI AG",

number = "5",

}

RIS

TY - JOUR

T1 - Facile access to Fe(III)-complexing cyclic hydroxamic acids in a three-component format

AU - Chupakhin, Evgeny

AU - Bakulina, Olga

AU - Dar’in, Dmitry

AU - Krasavin, Mikhail

PY - 2019/3/1

Y1 - 2019/3/1

N2 - 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 Fe 3+ , which makes them suitable candidates for the above-mentioned applications.

AB - 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 Fe 3+ , which makes them suitable candidates for the above-mentioned applications.

KW - Azeotropic distillation

KW - Castagnoli–Cushman reaction

KW - Cyclic hydroxamic acids

KW - Cyclodehydration

KW - Homophthalic acid

KW - Hydroxylamine acetate

KW - Iron complexation

KW - Siderophores/chemistry

KW - Hydroxamic Acids/chemistry

KW - Coordination Complexes/chemical synthesis

KW - Ferric Compounds/chemical synthesis

KW - BACTERIAL SIDEROPHORES

KW - ANALOGS

KW - ONE-POT SYNTHESIS

KW - cyclodehydration

KW - cyclic hydroxamic acids

KW - hydroxylamine acetate

KW - homophthalic acid

KW - Castagnoli-Cushman reaction

KW - azeotropic distillation

KW - iron complexation

KW - CHEMISTRY

KW - CASTAGNOLI-CUSHMAN REACTION

UR - http://www.scopus.com/inward/record.url?scp=85062858420&partnerID=8YFLogxK

U2 - 10.3390/molecules24050864

DO - 10.3390/molecules24050864

M3 - Article

C2 - 30823493

AN - SCOPUS:85062858420

VL - 24

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 5

M1 - 864

ER -

ID: 39973473