Details

Autor(en) / Beteiligte

• Bandgar, Babasaheb P.
• Adsul, Laxman K.
• Chavan, Hemant V.
• Shringare, Sadanand N.
• Korbad, Balaji L.
• Jalde, Shivkumar S.
• Lonikar, Shrikant V.
• Nile, Shivraj H.
• Shirfule, Amol L.

Titel

Synthesis, biological evaluation, and molecular docking of N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-benzamide/amide derivatives as xanthine oxidase and tyrosinase inhibitors

Ist Teil von

• Bioorganic & medicinal chemistry, 2012-09, Vol.20 (18), p.5649-5657

Ort / Verlag

Amsterdam: Elsevier Ltd

Erscheinungsjahr

2012

Quelle

MEDLINE

Beschreibungen/Notizen

• A series of N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-benzamide/amide derivatives have been synthesized and investigated for their in vitro xanthine oxidase and tyrosinase inhibitory activities. Claisen–Schmidt condensation of 3-formyl-9-methylcarbazole with various amides of 3-aminoacetophenone afforded N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-benzamide/amide derivatives. All compounds were investigated for their in vitro xanthine oxidase (XO), tyrosinase and melanin production inhibitory activity. Most of the target compounds had more potent XO inhibitory activity than the standard drug (IC50=4.3–5.6μM). Interestingly, compound 7q bearing cyclopropyl ring was found to be the most potent inhibitor of XO (IC50=4.3μM). Molecular modelling study gave an insight into its binding modes with XO. Compounds 7a, 7d, 7e, 7g, and 7k were found to be potent inhibitors of tyrosinase (IC50=14.01–17.52μM). These results suggest the possible use of these compounds for the design and development of novel XO and tyrosinase inhibitors.