Enols as potent antibacterial agents.
This paper describes the discovery of alpha-trifluoroketoacetamides as potent antibacterial agents against Gram-positive organisms. The initial SAR indicates that the aryl ethyl side chain is essential in maintaining antibacterial activity. The SAR observations have been utilized to design a bioisostere for the alpha-trifluoroketoacetamide with good activity against Gram-positive organisms.
Thorarensen
A
A
Department of Medicinal Chemistry, Pharmacia, 7254-209-615, Kalamazoo, MI 49007-4940, USA. atli.thorarensen@pharmacia.com
Zurenko
G E
GE
Sweeney
M T
MT
Marotti
K R
KR
Boyle
T P
TP
D000081:Acetamides / Q000138:chemical synthesis / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D005463:Fluoroacetates; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014269:Trifluoroacetic Acid / Q000737:chemistry
D000081:Acetamides; D000900:Anti-Bacterial Agents; D005463:Fluoroacetates; C030688:trifluoroacetamide; D014269:Trifluoroacetic Acid