Micelles catalyzed chemo- and regio-selective one pot and one step synthesis of 2,3,5,6-tetrakis(alkyl and arylsulfanyl)-1,4-benzoquinones and 2,5-diaminosubstituted-1,4-benzoquinones “In-Water” and their biological evaluation as antibacterial and antifun

Chemo- and regio-selective one pot and one step synthesis of novel 2,3,5,6-tetrakis (substituted thio)cyclohexa-2,5-diene-1,4-diones (4d–14), 2,5-dichloro-3,6-diaminocyclohexa-2,5-diene-1,4-diones and 2,5-diaminocyclohexa-2,5-diene-1,4-diones (16) by economical green methodology approach using LD (Laundry detergent) as a catalyst “In-Water” by nucleophilic addition and substitution reactions of 1,4-benzoquinone and chloranil with sulfur and nitrogen nucleophiles in high yields has been demonstrated. The antifungal profile of 4 and 16 indicates that compounds 4d and 16f had better antifungal activity compared to clinically prevalent antifungal drugs Fluconazole, 5-Fluorocytosine and Clotrimazole against Sporothrix schenckii and Trichophyton mentagraphytes. 16f had also been found to possess better antibacterial activity compared to Ampicillin in vitro against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 16f did not exhibit any toxicity towards mammalian cells L929.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► “On-Water” and “In-Water” Nucleophilic addition and nucleophilic substitution reactions of 1,4-benzoquinone and chloranil. ► LD (Laundry detergent) as a novel surfactant in the synthesis of novel 1,4-benzoquinone derivatives. ► Novel lead antifungal and antibacterial agents.