Synthesis of 6-aminomethyl derivatives of benzopyran-4-one with dual biological properties: anti-inflammatory-analgesic and antimicrobial.
A series of 6-aminomethyl-2-aryl-1-benzopyran-4-one derivatives (10-24) were synthesized. The compounds were tested for anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation actions. Among the tested compounds, six compounds 11, 13, 16, 18, 21 and 23 showed higher degree of anti-inflammatory activity (>75% activity of standard drug ibuprofen). In addition to remarkable anti-inflammatory activity, analgesic activity was found to be comparable with that of the standard drug ibuprofen. Compounds 16 and 21 showed a significant GI protection (with respect to ulcerogenesis) and a marked decrease in lipid peroxidation values whereas compounds 11 and 16 were found to possess antimicrobial activity against Staphylococcus aureus, Escherichia coli, Rhizopus oryza and Penicillum citrum with an MIC of 10 microg/mL.
Hasan
S M
SM
Department of Pharmacy, College of Health Sciences, Al Jouf University, Sakaka, Al Jouf, Saudi Arabia. misbahhasan@yahoo.com
Alam
M M
MM
Husain
Asif
A
Khanna
Suruchi
S
Akhtar
Mymoona
M
Zaman
M S
MS
D000586:Amination; D000700:Analgesics / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D047309:Flavones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects*; D015227:Lipid Peroxidation / Q000187:drug effects; D008745:Methylation; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure
D000700:Analgesics; D000890:Anti-Infective Agents; D000893:Anti-Inflammatory Agents; D001578:Benzopyrans; D047309:Flavones