Mild and efficient synthesis of new tetraketones as lipoxygenase inhibitors and antioxidants.
A mild and efficient route to tetraketones (2-22) has been developed by way of tetraethyl ammonium bromide (Et(4)N(+)Br(- )) mediated condensation of dimedone (5,5-dimethylcyclohexane-1,3-dione, 1) with a variety of aldehydes. All these compounds showed significant lipoxygenase inhibitory activity and moderate to strong antioxidant potential. Compounds 19 (IC(50) = 7.8 microM), 22 (IC(50) = 12.5 microM), 3 (IC(50) = 16.3 microM), 11 (IC(50) = 17.5 microM) and 8 (IC(50) = 21.3 microM) showed significant inhibitory potential against lipoxygenase (baicalein, IC(50) = 22.4 microM). On the other hand compound 19 (IC(50) = 33.6 microM) also showed strong antioxidant activity compared to the standard (IC(50) = 44.7 microM). This study is likely to lead to the discovery of therapeutically efficient agents against very important disorders including inflammation, asthma, cancer and autoimmune diseases.
Maharvi
Ghulam M
GM
Pharmaceutical Research Centre, Karachi, Pakistan.
Ali
Samar
S
Riaz
Naheed
N
Afza
Nighat
N
Malik
Abdul
A
Ashraf
Muhammad
M
Iqbal
Lubna
L
Lateef
Mehreen
M
D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D013329:Structure-Activity Relationship
D000975:Antioxidants; D016166:Free Radical Scavengers; D007659:Ketones; D016859:Lipoxygenase Inhibitors