Discovery of isoxazolinone antibacterial agents. Nitrogen as a replacement for the stereogenic center found in oxazolidinone antibacterials

[Display omitted] A series of potential antimicrobial derivatives possessing bioisosteric replacements for the central oxazolidinone ring found in oxazolidinone antibacterials have been prepared. The design concept involved replacement of the requisite sp 3-hybridized stereogenic center found at the...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2004-09, Vol.14 (18), p.4735-4739
Main Authors: Snyder, Lawrence B., Meng, Zhaoxing, Mate, Robert, D’Andrea, Stanley V., Marinier, Anne, Quesnelle, Claude A., Gill, Patrice, DenBleyker, Kenneth L., Fung-Tomc, Joan C., Frosco, MaryBeth, Martel, Alain, Barrett, John F., Bronson, Joanne J.
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibacterial
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Bioisostere
Biological and medical sciences
Gram-Negative Bacteria - drug effects
Gram-Positive Bacteria - drug effects
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Isoxazoles - pharmacology
Isoxazolinone
Medical sciences
Microbial Sensitivity Tests
Models, Molecular
Nitrogen - chemistry
Oxazolidinone
Oxazolidinones - chemistry
Oxazolone - analogs & derivatives
Oxazolone - chemical synthesis
Oxazolone - chemistry
Oxazolone - pharmacology
Pharmacology. Drug treatments
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrroles - pharmacology
Stereoisomerism
Structure-Activity Relationship
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Summary:[Display omitted] A series of potential antimicrobial derivatives possessing bioisosteric replacements for the central oxazolidinone ring found in oxazolidinone antibacterials have been prepared. The design concept involved replacement of the requisite sp 3-hybridized stereogenic center found at the 5-position of the oxazolidinone with a nitrogen atom. The synthesis and antibacterial activity of three such ring systems, the benzisoxazolinones, pyrroles, and isoxazolinones is described.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2004.06.076