Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid.
Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.
D000284:Administration, Oral; D000818:Animals; D002506:Cephalexin / Q000494:pharmacology / Q000627:therapeutic use; D002511:Cephalosporins / Q000138:chemical synthesis / Q000494:pharmacology*; D055598:Chemical Phenomena; D002621:Chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D006193:Haemophilus influenzae / Q000187:drug effects; D007211:Indoles / Q000138:chemical synthesis / Q000494:pharmacology* / Q000627:therapeutic use; D051379:Mice; D011008:Pneumococcal Infections / Q000188:drug therapy; D013203:Staphylococcal Infections / Q000188:drug therapy; D013211:Staphylococcus aureus / Q000187:drug effects; D013290:Streptococcal Infections / Q000188:drug therapy; D013291:Streptococcus / Q000187:drug effects; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis / Q000494:pharmacology*
D002511:Cephalosporins; D007211:Indoles; D013876:Thiophenes; D002506:Cephalexin; D005998:Glycine