1.
J Med Chem
; 36(3): 421-3, 1993 Feb 05.
Article
in English
| MEDLINE
| ID: mdl-8381185
2.
J Med Chem
; 18(4): 403-8, 1975 Apr.
Article
in English
| MEDLINE
| ID: mdl-1091736
ABSTRACT
The exo-methylene group in esters of 7-acylamido- and 7-amino-3-methylenecephams was ozonized to give 3-hydroxy-3-cephems. Conditions are described to effect a selective N-acylation of a 3-hydroxy-3-cephem nucleus ester. Vilsmeier reagents converted 7-acylamido-3-hydroxy compounds to 3-halo-3-cephem derivatives. Diazomethane converted the 3-hydroxy compounds to 3-methoxy-3-cephem derivatives. Removal of the ester-protecting group at the C4-carboxyl afforded a select group of cephalosporins with direct halo and methoxy substitution at C3. A number of these compounds are potent antibiotics.
Subject(s)
Cephalosporins/chemical synthesis , Cephalosporins/pharmacology , Enterobacter/drug effects , Escherichia coli/drug effects , Klebsiella pneumoniae/drug effects , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Penicillin Resistance , Salmonella/drug effects , Serratia marcescens/drug effects , Shigella/drug effects , Staphylococcus/drug effects , Structure-Activity Relationship
3.
J Am Chem Soc
; 96(15): 4986-7, 1974 Jul 24.
Article
in English
| MEDLINE
| ID: mdl-4604213
Subject(s)
Cephalosporins/chemical synthesis , Cephalosporins/pharmacology , Enterobacter/drug effects , Escherichia coli/drug effects , Klebsiella pneumoniae/drug effects , Microbial Sensitivity Tests , Penicillin Resistance , Salmonella/drug effects , Shigella/drug effects , Staphylococcus/drug effects , Structure-Activity Relationship
4.
J Org Chem
; 38(17): 2994-9, 1973 Aug 24.
Article
in English
| MEDLINE
| ID: mdl-4741304
5.
J Antibiot (Tokyo)
; 25(4): 248-50, 1972 Apr.
Article
in English
| MEDLINE
| ID: mdl-4340568
6.
J Org Chem
; 36(9): 1259-67, 1971 May 07.
Article
in English
| MEDLINE
| ID: mdl-4995070