Long-chain 3-acyl-4-hydroxycoumarins: structure and antibacterial activity.
By reacting 4-hydroxycoumarin with long-chain acyl chlorides, a number of new 3-acyl derivatives were prepared and the relationship was studied between their structures and activities against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, and Propionibacterium acnes ATCC 11827. Antibacterial activity was associated with enolic tautomers of a tricarbonylmethane group bearing a lipophilic side chain (undec-10-enoyl, undec-10-ynoyl, palmitoyl or octadec-9-enoyl). A newly synthesized 2-acyl derivative of 2H-indene-1,3-dione containing the same tricarbonylmethane motif showed a comparable activity.
Cravotto
Giancarlo
G
Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Torino, Italy. giancarlo.cravotto@unito.it
Tagliapietra
Silvia
S
Cappello
Rossella
R
Palmisano
Giovanni
G
Curini
Massimo
M
Boccalini
Marco
M
D015110:4-Hydroxycoumarins / Q000138:chemical synthesis* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013211:Staphylococcus aureus / Q000187:drug effects; D013212:Staphylococcus epidermidis / Q000187:drug effects; D013329:Structure-Activity Relationship
D015110:4-Hydroxycoumarins; D000900:Anti-Bacterial Agents