Synthesis, antimicrobial and DNA cleavage studies of some 4-aryloxymethylcoumarins obtained by reaction of 4-bromomethylcoumarins with bidentate nucleophiles

• Published in: Medicinal chemistry research Vol. 21; no. 9; pp. 2603 - 2614
• Main Authors: Makandar, Shabana Banu N., Basanagouda, Mahantesha, Kulkarni, Manohar V., Pranesha, Rasal, Vijaykumar P.
• Format: Journal Article
• Language: English
• Published: New York Springer-Verlag 01.09.2012
• Subjects: Biochemistry; Biomedical and Life Sciences; Biomedicine; Cell Biology; Original Research; Pharmacology/Toxicology; Microbial, DNA; 3-Aminophenol; 3-Diethylaminophenol; Coumarin; Resorcinol
• ISSN: 1054-2523; 1554-8120
• DOI: 10.1007/s00044-011-9785-z

Symmetrical bidentate nucleophiles such as resorcinol have been made to react with 4-bromomethylcoumarins in a cascaded manner to obtain mono and bis-4-aryloxymethylcoumarins by a room temperature allylic nucleophilic displacement. Unsymmetrical nucleophiles such as 3-acetylaminophenol and 3-diethylaminophenol have been used to generate 4-aryloxymethylcoumarins. All the compounds have been analyzed by spectral methods and subjected to preliminary antibacterial, antifungal and DNA cleavage studies. The results showed that the compounds bearing methoxy, chloro and bromo substituents at C6-position of coumarin showed higher activity. Graphical Abstract Symmetrical bidentate nucleophiles such as resorcinol, and unsymmetrical nucleophiles, 3-acetylaminophenol and 3-diethylaminophenol have been made to react with 4-bromomethylcoumarins in a cascaded manner to obtain corresponding 4-aryloxymethylcoumarins. All the compounds have been analyzed by spectral methods and subjected to preliminary antibacterial, antifungal and DNA cleavage studies.