99651-36-2Relevant academic research and scientific papers
Allyl and propargyl substituted penam sulfones as versatile intermediates toward the syntheses of new β-lactamase inhbitors
Sandanayaka, Vincent P.,Feigelson, Gregg B.,Prashad, Amar S.,Yang, Youjun,Petersen, Peter J.
, p. 997 - 1000 (2007/10/03)
Several alkenyl derivatives were prepared using allyl penam sulfone as the key intermediate. Isomers of these derivatives having β configuration at C-6 showed potent acitivity 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.
6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases I
Bitha, Panayota,Li, Zhong,Francisco, Gerardo D.,Rasmussen, Beth A.,Lin, Yang-I
, p. 991 - 996 (2007/10/03)
Five 6-(1-hydroxyalkyl)penam sulfone derivatives and two 6- (hydroxymethyl)penams were synthesized for β-lactamase inhibitor screens. The substituent effects and stereochemical requirements of 6α-and 6β-(1- hydroxyalkyl) groups for the biological activity of penam sulfone derivatives were investigated. Of these substituents, only the 6β-hydroxymethyl group of 15 improved the activity of sulbactam against both TEM-1 and AmpC β- lactamases. The sulfone moiety is required for the enhancement of the β- lactamase inhibitory activity. 6β-Hydroxymethylsulbactam (15) was able to restore the activity of piperacillin in vitro and in vivo against various β- lactamase producing microorganisms.
STEREOSELECTIVE SYNTHESIS OF 6α-HALOPENICILLANATES BY SAMARIUM(II) IODIDE PROMOTED REDUCTION OF 6,6-DIHALOPENICILLANATES
Kang, Han-Young,Pae, Ae Nim,Cho, Yong Seo,Choi, Kyung Il,Koh, Hun Yeong,Chung, Bong Young
, p. 2337 - 2342 (2007/10/03)
A mild an efficient samarium(II) iodide promoted-reduction of 6,6-dibromopenicillanates for stereoselective synthesis of 6α-bromopenicillanates has been developed.
Functionalization of Penicillins Via Iodine Atom Transfer Chemistry
Ziegler, Carl B.,Fields, Thomas L.
, p. 3919 - 3932 (2007/10/02)
Carbon-carbon bond formation via iodine atom transfer methodology represents a novel way to fuctionalize the 6-position of the penicillin nucleus.This work explores the synthetic scope and limitations to reactions of benzhydryl 6α-bromo-6β-iodopenicillana
6-(SUBSTITUTED)METHYLENE-PENICILLANIC AND 6-(SUBSTITUTED)HYDROXYMETHYL-PENICILLANIC ACIDS AND DERIVATIVES THEREOF
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, (2008/06/13)
Beta-lactamase inhibiting compounds of the formula: or a pharmaceutically acceptable acid addition or carboxylate salt thereof; where n is zero, 1 or 2; X.3 is H or Br, R1 is H, the residue of certain carboxy-protecting groups or the residue of an ester group readily hydrolyzable in vivo; one of R12 and R13 is H and the other is vinyl, certain aryl, alkylthio, alkylsulfonyl or certain heterocyclyl, aminomethyl, thiocarboxamido or amidino groups; one or R2 and R3 is H and the other is as disclosed for the other of R12 and R13, or is Cl or CH2 OH, and R18 is H or certain acyl groups; intermediates useful in their production, methods for their preparation and use, and pharmaceutical compositions containing them
β-Bromopenicillanic acid sulfone
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, (2008/06/13)
(2S,5R,6S)-6β-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, S,S-dioxide, physiologically acceptable salts thereof and readily hydrolyzable ester thereof inhibit the action of the β-lactamase enzyme RTEM.
