Synthesis and biological activities of 2,6-diaryl-3-methyl-4-piperidone derivatives.
In the present study, a new series of 2,6-diaryl-3-methyl-4-piperidones was synthesized by Mannich reaction (condensation) of ethyl-methyl ketone, substituted aromatic aldehydes and ammonium acetate. Oximes and thiosemicarbazone derivatives of 2,6-diaryl-3-methyl-4-piperidones were synthesized by reaction with hydroxylamine hydrochloride and thiosemicarbazide respectively. The chemical structures were confirmed by means of IR, 1H-, 13C-NMR and mass spectral data. The compounds were screened for acute toxicity, analgesic, local anaesthetic and antifungal activity. 2-(4-Methylphenyl)-3-methyl-6-(4-chlorophenyl)-piperidin-4-one 2 exhibited the highest analgesic and local anaesthetic activity. The oximes and thiosemicarbazones were completely devoid of analgesic and local anaesthetic activity. 2-(4-Methylphenyl)-3-methyl-6-(4-hydroxyphenyl)-piperidin-4-oxime 21 and 2-(4-methoxyphenyl)-3-methyl-6-(4-chlorophenyl)-piperidin-4-oxime 17 exhibited potent antifungal activity against Aspergillus niger. Antifungal activity against Candida albicans was observed only with 2-(4-dimethylaminophenyl)-3-methyl-6-(4-chlorophenyl)-piperidin-4-oxime 20. 2,6-Diaryl-3-methyl-4-piperidones did not exhibit antifungal property.
Rameshkumar
Natesh
N
Department of Pharmaceutical Chemistry, C. L. Baid Metha College of Pharmacy, Jyothi Nagar, Thorapakkam, Chennai, India. clbmcpl@md4.vsnl.net.in
Veena
Anantharaman
A
Ilavarasan
Raju
R
Adiraj
Mandaleeswaran
M
Shanmugapandiyan
Pitchaimuthu
P
Sridhar
Seshaiah Krishnan
SK
D000700:Analgesics / Q000138:chemical synthesis / Q000494:pharmacology; D000779:Anesthetics, Local / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice; D010147:Pain Measurement / Q000187:drug effects / Q000379:methods; D010881:Piperidones / Q000138:chemical synthesis* / Q000494:pharmacology*; D011898:Ranidae
D000700:Analgesics; D000779:Anesthetics, Local; D000935:Antifungal Agents; D010881:Piperidones