Synthesis and SAR evaluation of oxadiazolopyrazines as selective Haemophilus influenzae antibacterial agents.
The parallel synthesis and antibacterial activity of 5-hydroxy[1,2,5] oxadiazolo[3,4-b]pyrazines is reported. The compounds were synthesized by condensing diaminofurazan with alpha-keto acids to give a variety of aryl-substituted analogues. Halogenated phenyl groups at C-6 give rise to the greatest Haemophilus influenzae antibacterial activity.
Beebe
Xenia
X
Infectious Disease Research, Abbott Laboratories, Abbott Park, IL 60064, USA. xenia.b.searle@abbott.com
Nilius
Angela M
AM
Merta
Philip J
PJ
Soni
Niru B
NB
Bui
Mai H
MH
Wagner
Rolf
R
Beutel
Bruce A
BA
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006193:Haemophilus influenzae / Q000187:drug effects* / Q000254:growth & development; D006801:Humans; D008826:Microbial Sensitivity Tests / Q000379:methods; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000494:pharmacology*; D011719:Pyrazines / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D010069:Oxadiazoles; D011719:Pyrazines