Development of natural perfume as potential fungicide candidates: construction and biological evaluation of vanillin analogs bearing the 1,3,4-oxadiazole/1,3-thiazolidin-4-one fragments

Abstract

Two series of vanillin derivatives containing 1,3,4-oxadiazole and 1,3-thiazolidin-4-one scaffolds were prepared and evaluated for their antifungal activity. The results revealed that compounds 6j (29.73 μg/ml) and 7a (38.15 μg/ml) displayed excellent inhibitory activity against the spore of Fusarium solani. The inhibitory activity of compound 7d (10.53 μg/ml) against the spore of Alternaria solani was more than 42-fold that of vanillin. Compound 7a (37.54 μg/ml) showed better antifungal activity against the spore of B. cinerea than positive controls. The cytotoxicity assay confirmed that compounds 6k, 7a, and 7d showed good selectivity and less toxicity to normal mammalian cells.

Keywords:

• Natural perfume
• vanillin
• 1,3,4-oxadiazole
• 1,3-thiazolidin-4-one
• antifungal activity

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (Grant Nos. 31700300 and 21702129), the Basic Research Program of Shanxi Province (Free exploration project) (Grant Nos. 202103021224167 and 202103021224121), and the Subproject of National Key Research and Development Plan (Grant No. 2021YFD1600603-06) for the financial ­support in the present research.

Disclosure statement

No potential conflict of interest was reported by the author(s).