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Synthesis and Antioxidant Activity of New Tetrahydro‐Naphthalene‐Indole Derivatives as Retinoid and Melatonin Analogs
Author(s) -
AtesAlagoz Zeynep,
Coban Tulay,
Buyukbingol Erdem
Publication year - 2006
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200500177
Subject(s) - melatonin , retinoid , chemistry , fenretinide , indole test , lipid peroxidation , pharmacology , stereochemistry , antioxidant , biochemistry , retinoic acid , medicine , gene
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.