Aziridine‐Functionalized 1,3,5‐Triazine Derivatives as Promising Anticancer Agents: Synthesis, DFT Study, DNA Binding Investigations and In Vitro Cytotoxic Activity

Herein, we report a synthesis and characterization of aziridine‐functionalized 1,3,5‐triazine derivatives. Electronic structure and the most preferable geometry of substances were calculated by DFT method. DNA binding investigations were conducted as part of the biomedicinal research as well as the...

Full description

Saved in:

Bibliographic Details
Published in:	Journal of heterocyclic chemistry Vol. 61; no. 11; pp. 1801 - 1806
Main Authors:	Protas, Aleksandra V., Mikolaichuk, Olga V., Popova, Еlena А., Timoshchuk, Kirill V., Kornyakov, Ilya V., Maistrenko, Dmitrii N., Molchanov, Oleg E., Sharoyko, Vladimir V., Semenov, Konstantin N.
Format:	Journal Article
Language:	English
Published:	Chichester, UK John Wiley & Sons, Inc 01-11-2024 Wiley Subscription Services, Inc
Subjects:	1,3,5‐triazine aziridine Binding cytotoxic activity Density functional theory dioxane Electronic structure In vitro methods and tests interaction with DNA MTT test Synthesis
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	Herein, we report a synthesis and characterization of aziridine‐functionalized 1,3,5‐triazine derivatives. Electronic structure and the most preferable geometry of substances were calculated by DFT method. DNA binding investigations were conducted as part of the biomedicinal research as well as the cytotoxic activity of these compounds was evaluated using in vitro assays toward Huh‐7 and A549 cancer cell lines and HEK‐293 normal cell line. The results demonstrate that some of the synthesized compounds exhibit potent cytotoxic activity ([5‐[[4,6‐bis(aziridin‐1‐yl)‐1,3,5‐triazin‐2‐yl]amino]‐2,2‐dimethyl‐1,3‐dioxan‐5‐yl]methanol (1) and 4,6‐di(aziridine‐1‐yl)‐N‐(2,2,5‐trimethyl‐1,3‐dioxane‐5‐yl)‐1,3,5‐triazine‐2‐amine (9)), making them potential candidates for further development as anticancer agents. In this study, we present the synthesis and characterization and biological activity of aziridine‐functionalized 1,3,5‐triazine derivatives. The electronic structure of the substances was also determined.
Bibliography:	Funding The work was carried out with the financial support of the Ministry of Health of the Russian Federation. “Creation and evaluation of antitumor activity of conjugates of unannelated 1,3,5‐triazinyl‐tetrazoles with targeted delivery molecules to targets in the tumor cell microenvironment.”
ISSN:	0022-152X 1943-5193
DOI:	10.1002/jhet.4908