X-ray structural analysis, antioxidant and cytotoxic activity of newly synthesized salicylic acid derivatives

Djurendić, Evgenija A., Dojčinović-Vujašković, Sanja V., Sakač, Marija N., Jovin, Emilija Dj., Kojić, Vesna V., Bogdanović, Gordana M., Klisurić, Olivera R., Stanković, Slobodanka M., Lazar, Dušan V., Fabian, Laszlo and Penov-Gaši, Katarina M. (2009) X-ray structural analysis, antioxidant and cytotoxic activity of newly synthesized salicylic acid derivatives. Journal of Structural Chemistry, 21 (1). pp. 67-78. ISSN 1573-8779

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New salicylic (2-hydroxybenzoic) acid derivatives 1–6 were prepared by conventional heating or microwave irradiation of a mixture consisting of methyl salicylate and the corresponding amino alcohol (2,2'-dihydroxydiethylamine, 2,2',2?-trihydroxytriethylamine or N-phenyl-2,2'-dihydroxydiethylamine) and metallic sodium as catalyst. For compounds 1, 3, and 5 X-ray structure analysis was performed, as well as molecular mechanics calculations (MMC), to define their conformation in terms of their energy minima. Comparison of crystal and MMC structures for these three compounds (1, 3, and 5) revealed that the intramolecular hydrogen bonds play an important role, stabilizing conformation of the most part of the molecule. The antioxidant activity and cytotoxicity of the synthesized derivatives were evaluated in a series of in vitro tests. The newly synthesized compounds exhibited strong activity against hydroxyl radical, as well as promising lipid peroxidation inhibition. The study showed that the electronic effects of the groups at the N atom are responsible for neutralization of the OH radical, i.e., antioxidant activity. Compounds 1–3 exhibited sub-micromolar cytotoxicity against HeLa S3, whereas compounds 1, 3 and 5 efficiently inhibited the growth of PC3 cells.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Faculty of Science > School of Pharmacy
UEA Research Groups: Faculty of Science > Research Groups > Drug Delivery and Pharmaceutical Materials (former - to 2017)
Faculty of Science > Research Groups > Pharmaceutical Materials and Soft Matter
Depositing User: Rachel Smith
Date Deposited: 15 Mar 2011 15:29
Last Modified: 06 Jan 2023 16:30
URI: https://ueaeprints.uea.ac.uk/id/eprint/26261
DOI: 10.1007/s11224-009-9524-y

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