Synthesis and biological evaluation of O-methyl and O-ethyl NSAID hydroxamic acids.
This paper reports the synthesis of O-methyl and O-ethyl NSAID hydroxamic acids, their antimicrobial activities, and their ability to inhibit urease and soybean lipoxygenase activities. Ibuprofen and fenoprofen hydroxamic acids with free hydroxy groups present the highest antimicrobial activity, while indomethacin and diclofenac analogs show significantly lower antimicrobial activity. Diclofenac hydroxamic acid 4e exerts the highest anti-urease activity. Indomethacin O-ethyl hydroxamic acid 3h and ibuprofen O-benzyl hydroxamic acid 4b exert significant inhibitory activities on soybean lipoxygenase. Fenoprofen and indomethacin O-ethyl hydroxamic acids 3b and 3h and diclofenac and indomethacin O-benzyl analogs 4g and 4i highly inhibit lipid peroxidation. The highest antioxidant activity was shown by fenoprofen derivative 3b.
Rajić
Zrinka
Z
Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia.
Perković
Ivana
I
Butula
Ivan
I
Zorc
Branka
B
Hadjipavlou-Litina
Dimitra
D
Pontiki
Eleni
E
Pepeljnjak
Stjepan
S
Kosalec
Ivan
I
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000494:pharmacology; D000975:Antioxidants; D001419:Bacteria / Q000187:drug effects; D006877:Hydroxamic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D015227:Lipid Peroxidation / Q000187:drug effects*; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D015394:Molecular Structure; D014510:Urease / Q000037:antagonists & inhibitors
D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D006877:Hydroxamic Acids; D016859:Lipoxygenase Inhibitors; D014510:Urease