New antibacterial tetrahydro-4(2H)-thiopyran and thiomorpholine S-oxide and S,S-dioxide phenyloxazolidinones.
Combinatorial libraries of N-acylated 5-(S)-aminomethyloxazolidinone derivatives of S-oxide and S,S-dioxide tetrahydro-4(2H)-thiopyranyl and thiomorpholine phenyloxazolidinone series have been synthesized on a solid phase and evaluated for antimicrobial activity. Several novel potent leads have been identified, including orally active oxazolidinones with enhanced activity against respiratory tract infection pathogens Haemophilus influenzae and Moraxella catarrhalis.
Singh
Upinder
U
Vicuron Pharmaceuticals Inc., 34790 Ardentech Court, Fremont, CA 94555, USA.
Raju
B
B
Lam
Stuart
S
Zhou
Joseph
J
Gadwood
Robert C
RC
Ford
Charles W
CW
Zurenko
Gary E
GE
Schaadt
Ronda D
RD
Morin
Sara E
SE
Adams
Wade J
WJ
Friis
Janice M
JM
Courtney
Maria
M
Palandra
Joe
J
Hackbarth
Corinne J
CJ
Lopez
Sara
S
Wu
Charlotte
C
Mortell
Kathleen H
KH
Trias
Joaquim
J
Yuan
Zhengyu
Z
Patel
Dinesh V
DV
Gordeev
Mikhail F
MF
D000818:Animals; D000900:Anti-Bacterial Agents / Q000008:administration & dosage / Q000493:pharmacokinetics*; D001682:Biological Availability; D020650:Combinatorial Chemistry Techniques; D006192:Haemophilus Infections / Q000382:microbiology; D006193:Haemophilus influenzae / Q000187:drug effects*; D050356:Lipid Metabolism; D008297:Male; D008826:Microbial Sensitivity Tests; D001936:Moraxella catarrhalis / Q000187:drug effects*; D045828:Moraxellaceae Infections / Q000382:microbiology; D009025:Morpholines / Q000737:chemistry*; D023303:Oxazolidinones / Q000008:administration & dosage / Q000493:pharmacokinetics*; D010087:Oxides / Q000737:chemistry*; D017601:Oxygen Compounds / Q000493:pharmacokinetics*; D051381:Rats; D017207:Rats, Sprague-Dawley; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D009025:Morpholines; D023303:Oxazolidinones; D010087:Oxides; D017601:Oxygen Compounds; C028971:thiamorpholine