Water-soluble N-heterocyclic carbene precursors bearing benzimidazole core: synthesis, characterization, in vitro antioxidant and anticancer studies

Benzimidazole is an important member of the nitrogen-containing heterocyclic ring system since it confers surprisingly good biological properties in medicinal chemistry such as anticancer drug applications. Keeping this in mind, a new series of asymmetrical 1,3-disubstituted benzimidazolium salts we...

Full description

Saved in:
Bibliographic Details
Published in:Monatshefte für Chemie 2023-04, Vol.154 (3-4), p.429-440
Main Authors: Doğan Ulu, Öznur, Kuruçay, Ali, Özdemir, İsmail
Format: Article
Language:English
Subjects:
Analytical Chemistry
Anticancer properties
Antioxidants
Biological properties
Cancer
Chemical analysis
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Fibroblasts
Inorganic Chemistry
NMR spectroscopy
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Benzimidazole is an important member of the nitrogen-containing heterocyclic ring system since it confers surprisingly good biological properties in medicinal chemistry such as anticancer drug applications. Keeping this in mind, a new series of asymmetrical 1,3-disubstituted benzimidazolium salts were designed and reported. The compounds were synthesized by the reaction of 1-alkylbenzimidazoles with 2-(2-bromoethyl)-1,3-dioxane. The structures of all the compounds were determined using FT-IR, 1 H and 13 C NMR spectroscopy, LC–MS, and elemental analysis. The compounds were used for their antioxidant capacity by commercial kit assay. Further, these were screened for their cytotoxic effect against cell lines including MCF-7, A-549, and L929 using cisplatin as a reference drug. It resulted that the total antioxidant capacity values of the compounds were found to be quite low compared to the trolox equivalent. On the other side, most importantly, two compounds showed remarkable anticancer activity against MCF-7 and A-549 with IC 50 values of 18.06 and 20.44 µg/cm 3 , respectively, in comparison with cisplatin (IC 50  = 83.11 and 87.80 µg/cm 3 ). Furthermore, most of the compounds were found to be safe on normal L929 fibroblast cells compared to cancer cells (IC 50 values for healthy fibroblasts were 142.70–268.37 µg/cm 3 ). Taken together, the newly synthesized compounds containing benzimidazole core can be readily constructed and used as an attractive class of anticancer agents. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-023-03041-y