%0 Journal Article
%T Current Updates on Oxazolidinone and Its Significance
%A Neha Pandit
%A Rajeev K. Singla
%A Birendra Shrivastava
%J International Journal of Medicinal Chemistry
%D 2012
%I Hindawi Publishing Corporation
%R 10.1155/2012/159285
%X Oxazolidinone is a five-member heterocyclic ring exhibiting potential medicinal properties with preferential antibacterial activity. Scientists reported various synthetic procedures for this heterocyclic structure. Current review articles tried to cover each and every potential aspect of oxazolidinone like synthetic routes, pharmacological mechanism of action, medicinal properties, and current research activities. 1. Introduction The oxazolidinones are a new class of antimicrobial agents which have a unique structure and good activity against gram-positive pathogenic bacteria. Oxazolidinones are a class of compounds containing 2-oxazolidine in the structure. Oxazolidinones represent a new class of synthetic antibacterial agents active against multiple-resistant gram-positive pathogens, including methicillin-resistant Staphylococcus aureus (MRSA), penicillin-resistant streptococci, and vancomycin-resistant enterococci [1]. 1.1. Chemical Structure [2] Oxazolidinones are a class of azoles, oxazolidines with the carbon between the nitrogen and oxygen oxidized to a ketone, hence oxazolidinone (Figure 1). Figure 1: General Structure of oxazolidinone. 1.2. Nomenclature The antibacterial oxazolidinone template has a common nomenclature specially for aryl-5-(substituted) methyl-2-oxazolidinone. Throughout the paper, a consistent numbering system has been employed for description of the various oxazolidinone examined [3]. 2. Synthetic Schemes Earlier reviews have comprehensively covered the many synthetic approaches available for construction of the oxazolidinone ring. The most recent literature is replete with accounts of oxazolidinone templates that have seen extensive use as chiral auxiliaries. (1) Chiral Resolution Method. Early work relied upon chiral resolution as a means to optically active oxazolidinone. The amino-diol resulting from reaction of an aniline with glycidol was resolved using (R)-mandelic acid. Diethylcarbonate effected cyclization to the 5-(R)-hydroxymethyl-3-phenyl-2-oxazolidinone. Numerous approaches had been employed for converting the 5-(R)-methylalcohol moiety to the 5-(S)-acetamidomethyl group. Here tosylation of the alcohol was followed by azide displacement, reduction, and acylation of the amine [4] (Figure 2). Figure 2: Chiral resolution method. (2) Iodocyclocarbamation. Many of the Upjohn SAR studies were carried out with racemic oxazolidinone, synthesized by iodocyclocarbamation. A key modification was the addition of pyridine, crucial for circumventing untoward alkylative side reaction [5] (Figure 3). Figure 3:
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