Chitosan-sulfonic acid-catalyzed green synthesis of naphthalene-based azines as potential anticancer agents

Future Med Chem. 2024 Apr;16(7):647-663. doi: 10.4155/fmc-2023-0351. Epub 2024 Feb 22.

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.

Keywords: anticancer activity; azines; grinding; in silico study; molecular docking studies.

MeSH terms

  • Antineoplastic Agents* / chemistry
  • Catalysis
  • Chitosan*
  • Molecular Docking Simulation
  • Naphthalenes / pharmacology

Substances

  • Chitosan
  • Antineoplastic Agents
  • Naphthalenes