Synthesis and biological evaluation of nitrogen-containing chalcones as possible anti-inflammatory and antioxidant agents.
A novel series of nitrogen-containing chalcones were synthesized by Mannich reaction and were screened for anti-inflammatory related activities such as inhibition of cyclooxygenase-2 (COX-2), trypsin and beta-glucuronidase. The antioxidant potential was demonstrated using 1,1-diphenyl-2-picryl hydrazine (DPPH) radical scavenging activity. The results of the above studies shows that the compounds synthesized were found to be effective inhibitors of above pro-inflammatory enzymes, and were found to be possess moderate radical scavenging potential. Overall, the results of the studies reveal that the chalcones with N-methyl piperazine methyl and piperidine methyl substitution (4c, 3b, 4d, 6b) seems to be important for inhibition of beta-glucuronidase. Whereas the chalcones with piperidine methyl substitution (8b, 7b, 7c, 6c, 4b, 3c, 3b) were observed as effective inhibitors of COX-2, while the same compounds were found to be less reactive against COX-1 as compared to COX-2.
Bandgar
Babasaheb P
BP
Organic Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur 413 255, India. bandgar_bp@yahoo.com
Patil
Sachin A
SA
Gacche
Rajesh N
RN
Korbad
Balaji L
BL
Hote
Balwant S
BS
Kinkar
Santosh N
SN
Jalde
Shivkumar S
SS
D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051546:Cyclooxygenase 2 / Q000737:chemistry / Q000378:metabolism; D052246:Cyclooxygenase 2 Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005966:Glucuronidase / Q000037:antagonists & inhibitors / Q000378:metabolism; D009584:Nitrogen / Q000737:chemistry*; D014357:Trypsin / Q000737:chemistry / Q000378:metabolism; D014361:Trypsin Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D047188:Chalcones; D052246:Cyclooxygenase 2 Inhibitors; D014361:Trypsin Inhibitors; D051546:Cyclooxygenase 2; D005966:Glucuronidase; D014357:Trypsin; D009584:Nitrogen