Quinolone antibacterial agents substituted at the 7-position with spiroamines. Synthesis and structure-activity relationships

T P Culbertson; J P Sanchez; L Gambino; J A Sesnie

doi:10.1021/jm00170a035

Quinolone antibacterial agents substituted at the 7-position with spiroamines. Synthesis and structure-activity relationships

J Med Chem. 1990 Aug;33(8):2270-5. doi: 10.1021/jm00170a035.

Authors

T P Culbertson¹, J P Sanchez, L Gambino, J A Sesnie

Affiliation

¹ Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company, Ann Arbor, Michigan 48105.

PMID: 2374153
DOI: 10.1021/jm00170a035

Abstract

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.

Publication types

Comparative Study

MeSH terms

Bacteria / drug effects*
Chemical Phenomena
Chemistry
Gram-Negative Bacteria / drug effects
Gram-Positive Bacteria / drug effects
Molecular Structure
Piperazines / pharmacology
Pyrrolidines / pharmacology
Quinolines / chemical synthesis*
Quinolines / pharmacology
Spiro Compounds / chemical synthesis*
Spiro Compounds / pharmacology
Structure-Activity Relationship

Substances

Piperazines
Pyrrolidines
Quinolines
Spiro Compounds