Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents.
This is the first report on aurones as a new class of drugs with anti-inflammatory and antimicrobial agents. A series of 2,2-bisaminomethylated aurone analogues (4a-j) were synthesized by Mannich reaction from 1,3,5-trimethoxybenzene in three steps. The structures of the newly synthesized compounds were confirmed by IR, (1)H NMR and mass spectral analysis. All the synthesized compounds were screened against the pro-inflammatory cytokines (TNF-alpha, IL-6) and antimicrobial (antibacterial and antifungal) activity. Compounds 4a, 4b, 4c, 4d, and 4e showed promising results against IL-6 at 10 microM concentration (74-100%). Compounds 4a, 4b and 4c were found to be active against TNF-alpha (76-100%) at 10 microM. Interestingly, all compounds have shown good antimicrobial activity. Compounds 4d, 4e and 4f showed excellent antimicrobial activity as compared with standard drugs.
Bandgar
Babasaheb P
BP
Organic Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur 413255, MS, India. bandgar_bp@yahoo.com
Patil
Sachin A
SA
Korbad
Balaji L
BL
Biradar
Satish C
SC
Nile
Shivraj N
SN
Khobragade
Chandrahasya N
CN
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; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors; D000093242:Interleukin-6 Inhibitors
D000890:Anti-Infective Agents; D000893:Anti-Inflammatory Agents; D001572:Benzofurans; D014409:Tumor Necrosis Factor-alpha; D000093242:Interleukin-6 Inhibitors; C486837:aurone