Total Synthesis of Hinduchelins A-D, Stereochemical Revision of Hinduchelin A, and Biological Evaluation of Natural and Unnatural Analogues.

Childress, Elizabeth S; Garrison, Aaron T; Sheldon, Jessica R; Skaar, Eric P; Lindsley, Craig W

Childress, Elizabeth S; Garrison, Aaron T; Sheldon, Jessica R; Skaar, Eric P; Lindsley, Craig W.

Afiliación

Sheldon JR; Department of Pathology, Microbiology and Immunology , Vanderbilt University Medical Center , Nashville , Tennessee 37232 , United States.
Skaar EP; Department of Pathology, Microbiology and Immunology , Vanderbilt University Medical Center , Nashville , Tennessee 37232 , United States.

J Org Chem ; 84(10): 6459-6464, 2019 05 17.

Article en En | MEDLINE | ID: mdl-31039303

RESUMEN

Here, we report the first total synthesis of hinduchelins A-D, a family of nontoxic catechol derivatives from Streptoalloteichus hindustanus, possessing a druglike chemotype and modest iron-chelating ability. A concise synthesis was developed employing methyl 5-methyloxazole-4-carboxylate as a single starting material to provide hinduchelins A-D (and unnatural analogues) in only four steps and 5-15% overall yields; moreover, the stereochemistry of hinduchelin A was reassigned from ( S) to ( R). Biological evaluation confirmed that natural and unnatural hinduchelins are weak iron chelators (siderophores).

Asunto(s)

Catecoles/química; Catecoles/síntesis química; Quelantes del Hierro/química; Quelantes del Hierro/síntesis química; Actinobacteria/química; Técnicas de Química Sintética; Estereoisomerismo

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Catecoles / Quelantes del Hierro Idioma: En Revista: J Org Chem Año: 2019 Tipo del documento: Article Pais de publicación: Estados Unidos

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