Synthesis, structure, antimicrobial and antioxidant investigations of dicoumarol and related compounds.
Different substituted 3,3'-arylidenebis-4-hydroxycoumarins (1-7) and tetrakis-4-hydroxycoumarin derivative 8 are the final products when 4-hydroxycoumarin and aromatic aldehydes containing different groups in ortho, meta or para positions condense in boiling ethanol or acetic acid. Upon heating 3,3'-arylidenebis-4-hydroxycoumarins, and tetrakis-4-hydroxycoumarin derivative in anhydride acetic acid, the epoxydicoumarins (9-16) were formed. From a study of nuclear magnetic resonance and infrared spectra, intramolecularly hydrogen-bonded structures are proposed for the dicoumarols (1-8). A possible relationship between such hydrogen-bonded structures and the antimicrobial and the antioxidant activities of compounds 1-8 is suggested.
Hamdi
Naceur
N
Borj Cedria Higher Institute of Sciences and Technology of Environment, Touristic Road of Soliman, B.P. 95, 2050 Hammam-Lif, Tunisia. naceur.hamdi@isste.rnu.tn
Puerta
M Carmen
MC
Valerga
Pedro
P
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001728:Dicumarol / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D050296:Microbial Viability / Q000187:drug effects; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000975:Antioxidants; D001728:Dicumarol