Synthesis and anti-inflammatory activities of N-benzoylamino-1,2,3,6-tetrahydropyridine analogs.
The anti-inflammatory activity of N-benzoylamino-1,2,3,6-tetrahydropyridine (Fig. 1) has been previously described. Further structural modification of 1 indicated that anti-inflammatory activities were greatly influenced by the position and nature of substituents on the tetrahydropyridine ring moiety. Analogs of 1 with benzyl group at position 4 of the tetrahydropyridine ring moiety and substituents on the benzene moiety were synthesized (9a-90). The effect of these substituents on pharmacological activity was screened in vivo using the carrageenan-induced paw edema assay in male Sprague-Dawley rats. Analogs with electron-donating substituents at position 4 and 2 of the benzene moiety 9f, 90 and 9d exhibited significant anti-inflammatory activities, similar to that observed for the reference compound, indomethacin. In summary, at an early stage of efforts to establish structure-activity relationship within this series, we found that 9f is a promising lead compound chosen for further investigation.
Mochona
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B
College of Pharmacy and Pharmaceutical Sciences, Florida A&M University, Tallahassee, Florida 32307, USA.
Wilson
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T
Redda
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D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology*; D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D002351:Carrageenan; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002855:Chromatography, Thin Layer; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D007202:Indicators and Reagents; D007213:Indomethacin / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D017207:Rats, Sprague-Dawley; D013055:Spectrophotometry, Infrared
D000894:Anti-Inflammatory Agents, Non-Steroidal; D001549:Benzamides; D007202:Indicators and Reagents; C491687:N-benzoylamino-1,2,3,6-tetrahydropyridine; D011725:Pyridines; D002351:Carrageenan; D007213:Indomethacin