Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: antimicrobial, analgesic and antipyretic studies.
A series of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones (13c-21c) were synthesized by the base catalyzed nucleophilic substitution of N-chloroacetyl-2,6-diarylpiperidin-4-ones obtained from their corresponding 2,6-diarylpiperidin-4-ones with N-methylpiperazine. These newly synthesized compounds were characterized by one- and two-dimensional NMR spectral studies. In all the cases, the piperazine ring adopted normal chair conformation with equatorial orientation of methyl group irrespective of the non-chair conformations of the piperidin-4-one moiety. All the compounds were screened for their possible antibacterial and antifungal activities against a spectrum of microbial agents besides analgesic and antipyretic activities. These biological studies proved that compounds 17c/18c against bacterial and 18c/20c against fungal strains exhibited promising antimicrobial activities whereas 17c/19c and 18c/19c showed beneficial analgesic and antipyretic profiles, respectively, at a concentration of 60mg/kg and were also found to be more potent than the reference drug.
Aridoss
G
G
Department of Chemistry, Annamalai University, Annamalainagar-608002, Tamil Nadu, India.
Parthiban
P
P
Ramachandran
R
R
Prakash
M
M
Kabilan
S
S
Jeong
Yeon Tae
YT
D000700:Analgesics; D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D004353:Drug Evaluation, Preclinical; D005658:Fungi / Q000187:drug effects; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010146:Pain / Q000188:drug therapy; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship
D000700:Analgesics; D018712:Analgesics, Non-Narcotic; D000890:Anti-Infective Agents; D010880:Piperidines