Synthesis and antibiotic activity of 1-cycloalkoxymethyl-4-dimethylaminopyridinium and 1-[(1-alkoxy)ethyl]-4-dimethylaminopyridinium chlorides.
DMAP reacts readily with chloromethylcycloalkyl ethers and alpha-chloroethyl alkyl ethers to give stable (1a-1e) and unstable (2a-2h) pyridinium chlorides. Reaction of these chlorides with NaOH produces the corresponding 4-pyridones. All the chlorides synthesized showed antibiotic activity. Particularly high activity against microbes representing cocci, rods, fungi, and bacilli was shown by 1-cyclododecyloxymethyl-4-dimethylaminopyridinium chloride 1d and 1-[(1-dodecyloxy)ethyl]-4-dimethylaminopyridinium chloride 2f.
Pernak
J
J
Poznan University of Technology, Poland.
Michalak
L
L
Krysinski
J
J
Kuncewicz
Z
Z
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D011726:Pyridinium Compounds