Chitosan–Sulfonic Acid-Catalyzed Green Synthesis of Naphthalene-Based Azines as Potential Anticancer Agents

Abstract

Aim:

This study focuses on advancing green chemistry in anticancer drug discovery, particularly through the synthesis of azine derivatives with a naphthalene core using CS–SO₃H as a catalyst.

Methods:

Novel benzaldazine and ketazine derivatives were synthesized using (E)-(naphthalen-1-ylmethylene)hydrazine and various carbonyl compounds. The methods employed included thermal and grinding techniques, utilizing CS–SO₃H as an eco-friendly and cost-effective catalyst.

Results:

The approach resulted in high yields, short reaction times and demonstrated catalyst reusability. Cytotoxicity tests highlighted compounds 3b, 11 and 13 as potent against the HEPG2-1.

Conclusion:

This study successfully aligns with the objectives of eco-conscious drug development in organic chemistry. Molecular docking and in silico studies further indicate the potential of these ligands as antitumor medicines, with favorable oral bioavailability properties.

Graphical abstract

Keywords::

• anticancer activity
• azines
• grinding
• in silico study
• molecular docking studies

Supplementary data

To view the supplementary data that accompany this paper please visit the journal website at: www.tandfonline.com/doi/suppl/10.4155/fmc-2023-0351

Author contributions

AYA Alzahrani, SM Gomha, MEA Zaki, B Farag, FE Abdelgawad and MA Mohamed: supervision, investigation, methodology, resources, formal analysis, data curation, writing-original draft, writing review and editing. All authors have read and agreed to the published version of the manuscript.

Financial disclosure

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through the large group Research Project under grant number (RGP2/413/44). The authors have no other relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript apart from those disclosed.

Competing interests disclosure

The authors have no competing interests or relevant affiliations with any organization or entity with the subject matter or materials discussed in the manuscript. This includes employment, consultancies, honoraria, stock ownership or options, expert testimony, grants or patents received or pending, or royalties.

Writing disclosure

No writing assistance was utilized in the production of this manuscript.