Synthesis and biological evaluation of nitrogen-containing chalcones as possible anti-inflammatory and antioxidant agents

• Published in: Bioorganic & medicinal chemistry letters 2010-01, Vol.20 (2), p.730-733
• Main Authors: Bandgar, Babasaheb P., Patil, Sachin A., Gacche, Rajesh N., Korbad, Balaji L., Hote, Balwant S., Kinkar, Santosh N., Jalde, Shivkumar S.
• Format: Article
• Language: English
• Subjects: Anti-inflammatory; Anti-Inflammatory Agents - chemical synthesis; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - pharmacology; Antioxidant activity; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Biological and medical sciences; Bones, joints and connective tissue. Antiinflammatory agents; Chalcones - chemical synthesis; Chalcones - chemistry; Chalcones - pharmacology; Cyclooxygenase 2 - chemistry; Cyclooxygenase 2 - metabolism; Cyclooxygenase 2 Inhibitors - chemical synthesis; Cyclooxygenase 2 Inhibitors - chemistry; Cyclooxygenase 2 Inhibitors - pharmacology; Glucuronidase - antagonists & inhibitors; Glucuronidase - metabolism; Medical sciences; Nitrogen - chemistry; Nitrogen-containing chalcones; Pharmacology. Drug treatments; Trypsin - chemistry; Trypsin - metabolism; Trypsin Inhibitors - chemical synthesis; Trypsin Inhibitors - chemistry; Trypsin Inhibitors - pharmacology
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2009.11.068

A novel series of nitrogen-containing chalcones were synthesized and were screened for anti-inflammatory and antioxidant activity. Tested compounds ( 4c, 3b, 4d, 6b) were showed pro-inflammatory enzyme inhibitory activity. Whereas tested compounds ( 7b, 7c, 6c, 4b, 3c, 3b) were observed as effective inhibitors of COX-2. 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 β-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 β-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.