The Contribution of oxazolidinone frame to The biological activity of pharmaceutical drugs and natural products

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The Contribution of oxazolidinone frame to The biological activity of pharmaceutical drugs and natural products

Tema

ANTIINFECCIOSOS
PRODUCTOS NATURALES
FARMACOCINETICA
BACTERIAS
BIBLIOGRAFIA NACIONAL QUIMICA
2007

Abstract

The development of resistance by the antibiotics in the Gram-positive pathogenic bacteria over the last twenty years and continuing today has created a need for new antibiotic classes, which may be unaffected by existing bacterial resistance. The oxazolidin-2-ones represent not only a new class with a novel mechanism of action, but also satisfy the requirement for overcoming the resistance mechanisms. Both linezolid and eperozolid, the first chemical candidates, arose from the piperazine subclass, with the first one being chosen further development because of its enhanced pharmacokinetic properties. The main attractive traits of the oxazolidinone series has encouraged further work in the area, and the patent literature reveals that extensive chemical investigation is currently being made. The unexpected early resistance development emphasizes the need for further exploration of features of the oxazolidinone to eliminate these deficiencies. Recently, several changes, involving the C5 side chain as well the N-phenyl heterocyclic ring, give promise for such improvement. Oxazolidinone antibacterial agents comprise also ketolides, derivatives of macrolides, such as erythromycin A, with a newly formed carbamate cycle, with a largely unexplored potential. The oxazolidinone nucleus does not appear only in the structures of antimicrobial drugs, but a number of biological activities are connected with frameworks including the oxazolidinone ring. A partial list of these activities comprises enzyme inhibitors, agonists and antagonists, with a particular citation for a new generation of selective monoamino oxidase inhibitors (befloxatone). The oxazolidinone moiety was found in the structure of few biologically active natural products, such as (-)-cytoxazone and streptazolin. Moreover, in some cases the oxazolidinone ring has been chosen for the preparation of isosteric aza analogues of natural compounds (podophyllotoxin, pilocarpine) that can be more easily synthesised and more hardly inactivated. Finally, the participation of oxazolidinone chiral auxiliaries to several syntheses of natural products must be acknowledged.

Autor

Zappia, Giovanni
Delle Monache, Giuliano
Misiti, Domenico
Nevola, Laura
Botta, Bruno

Fuente

Mini Reviews in Medicinal Chemistry  v. 7, no. 4, 2007. -- p. 389-409

Editor

Bentham Science Publishers Ltd.

Fecha

2007

Derechos

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PDF

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Inglés

Tipo

Artículo

Identificador

ISSN 1389-5575
Fecha de agregación
December 30, 2014
Colección
Bibliografía Nacional Química
Tipo de Elemento
Document
Etiquetas
,
Citación
Zappia, Giovanni, “The Contribution of oxazolidinone frame to The biological activity of pharmaceutical drugs and natural products,” RIQUIM - Repositorio Institucional de la Facultad de Química - UdelaR, accessed June 27, 2022, http://riquim.fq.edu.uy/items/show/2369.
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