title: Synthesis and structure-activity relationships in the cefpirome series. II. Analogues of cefpirome with different 7-heteroarylacetamido and 3'-ammonium substituents.
abstract: The synthesis and antibacterial activity in vitro of 7-(2-heteroarylacetamido)-3-[(2,3- cyclopentenopyridinium)methyl]cephalosporins and of some related compounds with different ammonium functions in 3'-position are described. The 7-[5-amino-1,2,4-thiadiazol-3-yl] and the 7-[4-aminopyrimidin-2-yl] analogues of cefpirome and compounds with 3-aliphatic ammoniummethyl functions have excellent antibacterial activity. Cephalosporins with different N-heterocycles other than pyridine in 3'-position are less active than their 3-pyridiniummethyl analogues. Attachment of a pyridinium group to a cephem at C-3 via a thiomethyl or an aminomethyl bridge causes reduction of antibacterial activity.
authors.affiliation: Hoechst AG, Pharma Forschung, Frankfurt/Main, FRG.
authors.forename: R
authors.initials: R
authors.lastname: Lattrell
authors.forename: J
authors.initials: J
authors.lastname: Blumbach
authors.forename: W
authors.initials: W
authors.lastname: Duerckheimer
authors.forename: K
authors.initials: K
authors.lastname: Fleischmann
authors.forename: R
authors.initials: R
authors.lastname: Kirrstetter
authors.forename: N
authors.initials: N
authors.lastname: Klesel
authors.forename: B
authors.initials: B
authors.lastname: Mencke
authors.forename: K H
authors.initials: KH
authors.lastname: Scheunemann
authors.forename: W
authors.initials: W
authors.lastname: Schwab
authors.forename: H
authors.initials: H
authors.lastname: Seliger
mesh_terms: D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D004754:Enterobacter / Q000187:drug effects; D007709:Klebsiella / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D011549:Pseudomonas / Q000187:drug effects; D013291:Streptococcus / Q000187:drug effects; D013329:Structure-Activity Relationship; D000097572:Cefpirome
chemical_list: D002511:Cephalosporins; D000097572:Cefpirome