A non-lithiation route towards facile synthesis of bioactive 4, 9-dimethoxynaphthalide

Abstract

A simple, facile, and convenient route is adopted for the synthesis of 4,9-dimethoxynaphthalide (4,9-DMN); an analog of naturally occurring naphthalene lactone family. It is achieved without involving a tedious and hazardous lithiation step using 3-(bromomethyl)-1,4-dimethoxy-2-naphthaldehyde as key intermediate through base catalyzed oxidative cyclization resulting in a five-membered lactone ring. This compound exhibits significant anti-fungal activity against Candida albicans while it is found to be less toxic towards MCF-7 cancer cell line with IC₅₀ value less than 250 µM.

Graphical Abstract

Keywords:

• 4,9-dimethoxynaphthalide naphthalene lactone oxidative-cyclization anticancer

Acknowledgments

Authors are grateful to Dr. Mrs. Sujata S. Kale, Ex-Head, Department of Chemistry and Principal Prof. P. B. Buchade, Abasaheb Garware College for providing the necessary facilities.