Allyl and propargyl substituted penam sulfones as versatile intermediates toward the syntheses of new beta-lactamase inhibitors

V P Sandanayaka; G B Feigelson; A S Prashad; Y Yang; P J Petersen

doi:10.1016/s0960-894x(01)00148-2

Allyl and propargyl substituted penam sulfones as versatile intermediates toward the syntheses of new beta-lactamase inhibitors

Bioorg Med Chem Lett. 2001 Apr 23;11(8):997-1000. doi: 10.1016/s0960-894x(01)00148-2.

Authors

V P Sandanayaka¹, G B Feigelson, A S Prashad, Y Yang, P J Petersen

Affiliation

¹ Chemical Sciences and Infectious Diseases, Wyeth-Ayerst Research, Pearl River, NY 10965, USA. sandanv@war.wyeth.com

PMID: 11327608
DOI: 10.1016/s0960-894x(01)00148-2

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.

MeSH terms

Alkenes / chemical synthesis
Alkynes / chemical synthesis
Bacterial Proteins*
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / pharmacology*
Escherichia coli
Inhibitory Concentration 50
Molecular Conformation
Penicillanic Acid / analogs & derivatives
Penicillanic Acid / pharmacology
Sulfones / chemical synthesis
Sulfones / pharmacology*
Tazobactam
Triazoles / chemical synthesis
Triazoles / pharmacology*
beta-Lactamase Inhibitors*
beta-Lactamases

Substances

Alkenes
Alkynes
Bacterial Proteins
Enzyme Inhibitors
Sulfones
Triazoles
beta-Lactamase Inhibitors
methylacetylene
Penicillanic Acid
propylene
AmpC beta-lactamases
beta-Lactamases
beta-lactamase TEM-1
carbapenemase
Tazobactam