Synthesis and antioxidant activity of new tetrahydro-naphthalene-indole derivatives as retinoid and melatonin analogs.
A number of retinoid-related compounds represent classes of antioxidative and proapoptotic agents with promising potential in the treatment of neoplastic diseases. Indeed, the synthetic retinoid amide fenretinide [N-(4-hydroxyphenyl)retinamide] induces apoptosis of cancer cells and acts as a chemotherapeutic drug in cancer therapy. In the present work, and as a continuation of our studies on retinoid-type compounds, the synthesis of melatonin retinamide derivatives was studied as a novel series of melatonin retinoids, using the condensation reaction sequence involving tetrahydrotetramethylnaphthalene carboxylic acid and appropriate melatonin-type moieties. Despite of the weak DPPH inhibition activity pattern of the synthesized compounds, some of them showed a strong inhibition on lipid peroxidation (IVa-b, Va, and VIIa-c, 88, 96, 90, 94, 93, and 86%, respectively at 10(-4) M concentration) when melatonin (85% at 10(-4) M concentration) was used as a reference compound.
Ankara University, Faculty of Pharmacy Department of Toxicology, Ankara, Turkey. zates@pharmacy.ankara.edu.tr
Zeynep
Z
Ates-Alagoz
Tulay
T
Coban
Erdem
E
Buyukbingol
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000494:pharmacology; D066298:In Vitro Techniques; D015227:Lipid Peroxidation; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D008550:Melatonin / Q000031:analogs & derivatives*; D009281:Naphthalenes / Q000138:chemical synthesis / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D012176:Retinoids / Q000138:chemical synthesis / Q000494:pharmacology*; D013481:Superoxides / Q000737:chemistry
D000975:Antioxidants; D016166:Free Radical Scavengers; D009281:Naphthalenes; D012176:Retinoids; D013481:Superoxides; D008550:Melatonin