Issue 15, 2025

Solvent-free approach for the synthesis of 2,4-disubstituted quinolines using zeolites: evaluation of biological activity

Abstract

A simple one-step heterogeneous catalytic cyclization-based procedure was employed to prepare 2,4-disubstituted quinolines from ketones and 2-aminobenzophenones using Hβ zeolite as a catalyst in solvent-free conditions. Using a variety of substrates, the probabilities and constraints of catalytic activity were studied. Large scale studies validated the viability and effectiveness of scaling up this catalytic system. Furthermore, the catalyst has been employed repeatedly up to five times without any significant loss in its catalytic efficiency. This method provides a fascinating and green approach for synthesizing a broad range of 2,4-disubstituted quinoline derivatives utilizing simple starting materials and a heterogeneous catalyst in optimum reaction conditions. Furthermore, the anticancer potential of the synthesized compounds was evaluated in vitro against the PC-3, H460 and MDA-MB-231 cell lines. Cytotoxicity assays revealed that compounds 3c, 3q, and 3t exhibited significant anticancer activity against PC-3 cells, while compound 3m demonstrated potent activity against MDA-MB-231 cells. In addition, compounds 3d and 3f showed anti-cancer activity in H460 (lung cancer cells). Notably, compound 3aa exhibited broad-spectrum anticancer activity across all three tested cell lines. Further studies demonstrated that the selected compounds induced apoptosis and caused G1 or G2 phase cell cycle arrest, suggesting their potential anti-cancer activity through the regulation of cell cycle progression. Overall, these findings indicate that 2,4-disubstituted quinolines exhibit significant anti-cancer properties in breast, prostate and lung cancer cells.

Graphical abstract: Solvent-free approach for the synthesis of 2,4-disubstituted quinolines using zeolites: evaluation of biological activity

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
06 Jan 2025
Accepted
16 Mar 2025
First published
19 Mar 2025

New J. Chem., 2025,49, 6461-6468

Solvent-free approach for the synthesis of 2,4-disubstituted quinolines using zeolites: evaluation of biological activity

L. Madhuri, G. K. Sai, A. S. Teja, A. Vasu, A. S. S. S. S. Sudha, A. S. Balaji, T. J. Reddy and N. Narender, New J. Chem., 2025, 49, 6461 DOI: 10.1039/D5NJ00071H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements