Quinolone antibacterial agents substituted at the 7-position with spiroamines. Synthesis and structure-activity relationships.
A series of fluoroquinolone antibacterials having the 7-position (10-position of pyridobenzoxazines) substituted with 2,7-diazaspiro[4.4]nonane (4b), 1,7-diazaspiro[4.4]nonane (5a), or 2,8-diazaspiro[5.5]undecane (6b) was prepared, and their biological activities were compared with piperazine and pyrrolidine substituted analogues. Most exhibited potent Gram-positive and Gram-negative activity, especially when side chain 4b was N-alkylated.
Culbertson
T P
TP
Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company, Ann Arbor, Michigan 48105.
Sanchez
J P
JP
Gambino
L
L
Sesnie
J A
JA
D001419:Bacteria / Q000187:drug effects*; D055598:Chemical Phenomena; D002621:Chemistry; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D015394:Molecular Structure; D010879:Piperazines / Q000494:pharmacology; D011759:Pyrrolidines / Q000494:pharmacology; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D010879:Piperazines; D011759:Pyrrolidines; D011804:Quinolines; D013141:Spiro Compounds