Naslov
Priprava i biološka evaluacija novih hidroksipiridinonskih derivata
(Preparation and biological evaluation of novel hydroxypiridinone derivatives)

Autori
Dandić Andrea, Car Željka, Petrović Peroković Vesna

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
4th young scientists day Book of abstracts / Zvonko Antunović, Anea Mihajlovic - Osijek, 2022, 19-19

Skup
4. dan mladih istraživača

Mjesto i datum
Osijek, Hrvatska, 07.10.2022

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Domaća recenzija

Ključne riječi
adamantane, antiproliferative activity, 3-hydroxypyridin-4-ones, lipophilicity, structure-activity relationship study

Sažetak
3-Hydroxypyridin-4-ones are a well known class of heterocyclic compounds extensively studied due to their broad spectrum of biological activities (antibacterial, antidiabetes, antiprotozoal, antineurodegenerative and anticancer). In our previous work we investigated several para- substituted N-aryl-3-hydroxy-2-methylpyridin-4- ones as well as their ester adamantyl derivatives for their in vitro antitumor properties. All tested compounds showed antiproliferative activity ranging from moderate to strong on all inspected cell lines with lipophilic adamantane containing derivatives being active at low micromolar IC50 concentrations. In the continuation of our work novel meta- and para- substituted N-aryl-3- hydroxy-2-methylpyridin-4-ones were prepared with the aim of evaluating their in vitro antitumor properties on five cancer cell lines as well as normal cell line. Novel derivatives are distinguished from compounds prepared in previous research by a) position of the substituent on the aryl part of the molecule (meta-position) and b) type of the substituent on the aryl part of the molecule (alkyl group). Reactions were conducted with heating of aqueous solutions of starting materials, maltol and meta- or para- substituted anilines, in autoclave. Prepared 3-hydroxypyridin- 4-ones were additionally structurally modified by incorporating lipophilic units into pyridinone structure, primarily adamantyl unit, by Steglich esterification method. Structure of all prepared compunds were determined by 1H NMR and 13CNMR spectroscopy and/or MS/HRMS spectrometry. Antiproliferative activity of prepared compounds was examined and structure-activity relationship (SAR) was systematically researched in order to determine structural motifs responsible for their biological effect. On the basis of obtained results lead compounds were singled out whereby selective activity of compounds towards tumor versus normal cell lines was considered.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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