Affiliation:
1. Division of Organic Chemistry CSIR-National Chemical Laboratory (CSIR-NCL) Dr. Homi Bhabha Road Pune 411 008 India
2. Academy of Scientific and Innovative Research (AcSIR) Ghaziabad 201 002 India
3. Amity Institute of Biotechnology Amity University Uttar Pradesh Sector-125 Noida India
Abstract
AbstractEugenol and isoeugenol, secondary metabolites isolated from the plant Myristica fragrans have displayed antifungal activities against Aspergillus fumigatus (IC50 1900 μM). Compounds having conjugated unsaturation have been of great use as antifungals i. e. amphotericin B, nystatin and terbinafine etc. Hence, in the present study, we have designed and synthesised 1,3‐diynes by utilizing Glaser‐Hay and Cadiot‐Chodkiewicz coupling reactions to furnish possible antifungal agents. Synthesis of 1,6‐diphenoxyhexa‐2,4‐diyne derivatives was achieved by Cu(I) catalysed coupling of propargylated eugenol, isoeugenol, guaiacol, vanillin and dihydrogenated eugenol or eugenol in good to excellent yields. All the synthesized compounds were evaluated against pathogenic fungus A. fumigatus. Among all the synthesized compounds, one of the compounds was found to be exhibiting promising antifungal activity with IC50 value of 7.75 μM thereby suggesting that this type of scaffold could pave the way for developing new antifungal agents. The most active compound was found to be low cytotoxic when assayed against L‐132 cancer cell line. Effect of the most active compound on ergosterol biosynthesis has also been studied. Also, the most active compound exhibited significant anti‐biofilm activity although the concentration was found to be higher than its anti‐fungal activity. Morphological changes in the biofilm were remarkable under confocal laser scanning microscopy.
Subject
Organic Chemistry,General Pharmacology, Toxicology and Pharmaceutics,Molecular Medicine,Drug Discovery,Biochemistry,Pharmacology
Cited by
1 articles.
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