The synthesis and antibacterial activity of 1,3,4-Thiadiazole phenyl oxazolidinone analogues

Replacement of the morpholine C-ring of linezolid 1 with a 1,3,4-thiadiazolyl ring leads to oxazolidinone analogues 5 having potent antibacterial activity against both gram-positive and gram-negative organisms. Conversion of the C5 acetamide group to a thioacetamide further increases the potency of...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2003-12, Vol.13 (23), p.4193-4196
Main Authors: Thomasco, Lisa M, Gadwood, Robert C, Weaver, Elizabeth A, Ochoada, Jason M, Ford, Charles W, Zurenko, Gary E, Hamel, Judith C, Stapert, Douglas, Moerman, Judy K, Schaadt, Ronda D, Yagi, Betty H
Format: Article
Language:English
Subjects:
Acetamides - chemical synthesis
Acetamides - chemistry
Acetamides - pharmacology
Animals
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Gram-Positive Bacteria - drug effects
Linezolid
Microbial Sensitivity Tests
Oxazolidinones - chemical synthesis
Oxazolidinones - chemistry
Oxazolidinones - pharmacology
Phenols - chemistry
Rats
Structure-Activity Relationship
Thiadiazoles - chemistry
Thioacetamide - chemical synthesis
Thioacetamide - chemistry
Thioacetamide - pharmacology
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Summary:Replacement of the morpholine C-ring of linezolid 1 with a 1,3,4-thiadiazolyl ring leads to oxazolidinone analogues 5 having potent antibacterial activity against both gram-positive and gram-negative organisms. Conversion of the C5 acetamide group to a thioacetamide further increases the potency of these compounds. Replacement of the morpholine C-ring of linezolid 1 with a 1,3,4-thiadiazolyl ring leads to oxazolidinone analogues 5 having potent antibacterial activity against both gram-positive and gram-negative organisms. Conversion of the C5 acetamide group to a thioacetamide further increases the potency of these compounds.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2003.07.018