New 4,6-diacetyl resorcinol Mannich bases: synthesis and biological evaluation.
In the present study, a series of Mannich bases was synthesized by condensing 4,6-diacetylresorcinol with formaldehyde and some selected secondary amines following the Mannich reaction conditions. Findings revealed that Mannich reaction did not take place at the acetyl function but occurred on the aromatic ring position between the two hydroxyl groups. It was also observed that in one case instead of the desired base (3a), the dimer (4) of the starting material (4,6-diacetylresorcinol) having a methylene bridge could be isolated. The newly synthesized compounds were characterized on the basis of elemental analysis as well as 1H NMR and mass spectral data. The products have been evaluated for antiinflammatory, ulcerogenic and lipid peroxidation actions with some significant results.
Faculty of Pharmacy, Jamia Hamdard University, Department of Pharmaceutical Chemistry, Hamdard Nagar, New Delhi-110062, India.
Mohammed Sardaryar
MS
Khan
Asif
A
Husain
Sanjay
S
Sharma
D000588:Amines / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D002351:Carrageenan; D004195:Disease Models, Animal; D015195:Drug Design; D005260:Female; D005557:Formaldehyde / Q000737:chemistry; D007249:Inflammation / Q000139:chemically induced / Q000517:prevention & control; D015227:Lipid Peroxidation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008352:Mannich Bases; D013058:Mass Spectrometry; D015394:Molecular Structure; D051381:Rats; D017208:Rats, Wistar; D012118:Resorcinols / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D013276:Stomach Ulcer / Q000139:chemically induced; D013329:Structure-Activity Relationship
C526645:4,6-diacetylresorcinol; D000588:Amines; D000893:Anti-Inflammatory Agents; D008352:Mannich Bases; D012118:Resorcinols; D005557:Formaldehyde; D002351:Carrageenan