Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Design, Synthesis, and Evaluation of Novel Indole Hybrid Chalcones and Their Anticancer and Antioxidant Activity

Zuzana Kudličková
* ,
Radka Michalková
ORCID logo ,
Aneta Salayová
,
Marián Ksiažek
,
Mária Vilková
ORCID logo ,
Slávka Bekešová
,
Ján Mojžiš
* ORCID logo
Version 1 : Received: 1 September 2023 / Approved: 1 September 2023 / Online: 4 September 2023 (03:11:22 CEST)

A peer-reviewed article of this Preprint also exists.

Kudličková, Z.; Michalková, R.; Salayová, A.; Ksiažek, M.; Vilková, M.; Bekešová, S.; Mojžiš, J. Design, Synthesis, and Evaluation of Novel Indole Hybrid Chalcones and Their Antiproliferative and Antioxidant Activity. Molecules 2023, 28, 6583. Kudličková, Z.; Michalková, R.; Salayová, A.; Ksiažek, M.; Vilková, M.; Bekešová, S.; Mojžiš, J. Design, Synthesis, and Evaluation of Novel Indole Hybrid Chalcones and Their Antiproliferative and Antioxidant Activity. Molecules 2023, 28, 6583.

Abstract

The synthesis, anticancer and antioxidant activity of a series of indole-derived hybrid chalcones are reported here. First, using well known Claisen-Schmidt condensation method a set of 29 chalcones has been designed, synthesized, and consequently characterized. Subsequently, screening for the antiproliferative activity of the synthesized hybrid chalcones was performed on the on five cancer (HCT116, HeLa, Jurkat, MDA-MB-231 and MCF7) and two non-cancer (MCF-10A and Bj-5ta) cell lines. Chalcone 18c bearing 1-methoxyindole and catechol structural features, exhibited selective activity against cancer cell lines with IC50 values of 8.0 ± 1.4 µM (Jurkat) and 18.2 ± 2.9 µM (HCT116) and showed no toxicity to non-cancer cells. Furthermore, antioxidant activity was evaluated using tree different methods. The in vitro studies of radical scavenging activity utilizing DPPH radicals, as well as FRAP method, demonstrated the strong activity of catechol derivatives 18a-c. According to the ABTS radical scavenging assay, the 3-methoxy-4-hydroxy substituted chalcones 19a–c were slightly more favorable. In general, a series of 3,4-dihydroxychalcone derivatives showed properties as a lead compound for both antioxidant and anticancer activity.

Keywords

indole chalcone; antiproliferative activity; antioxidant activity; 2-fluoro substitution; hydroxy substitution

Subject

Chemistry and Materials Science, Medicinal Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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