title: Allyl and propargyl substituted penam sulfones as versatile intermediates toward the syntheses of new beta-lactamase inhibitors.
abstract: Several alkenyl derivatives were prepared using allyl penam sulfone as the key intermediate. Isomers of these derivatives having beta configuration at C-6 showed potent activity against CcrA enzyme. A new method was developed to prepare propargyl penam sulfone. The majority of the triazoles prepared by this route exhibited good activity against all three representative enzymes used for the inhibition assay.
authors.affiliation: Chemical Sciences and Infectious Diseases, Wyeth-Ayerst Research, Pearl River, NY 10965, USA. sandanv@war.wyeth.com
authors.forename: V P
authors.initials: VP
authors.lastname: Sandanayaka
authors.forename: G B
authors.initials: GB
authors.lastname: Feigelson
authors.forename: A S
authors.initials: AS
authors.lastname: Prashad
authors.forename: Y
authors.initials: Y
authors.lastname: Yang
authors.forename: P J
authors.initials: PJ
authors.lastname: Petersen
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis; D000480:Alkynes / Q000138:chemical synthesis; D001426:Bacterial Proteins; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D004926:Escherichia coli; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D010397:Penicillanic Acid / Q000031:analogs & derivatives / Q000494:pharmacology; D013450:Sulfones / Q000138:chemical synthesis / Q000494:pharmacology*; D000078142:Tazobactam; D014230:Triazoles / Q000138:chemical synthesis / Q000494:pharmacology*; D065093:beta-Lactamase Inhibitors; D001618:beta-Lactamases
chemical_list: D000475:Alkenes; D000480:Alkynes; D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D013450:Sulfones; D014230:Triazoles; D065093:beta-Lactamase Inhibitors; C022030:methylacetylene; D010397:Penicillanic Acid; C013658:propylene; C048795:AmpC beta-lactamases; D001618:beta-Lactamases; C034413:beta-lactamase TEM-1; C063912:carbapenemase; D000078142:Tazobactam