Three classes of fungicides were synthesized through a newly developed site-selective alkylation of 1,3,6′,3″-tetraazidokanamycin. The alkylation was done with 4, 6, 7, 8, 9, 10, 12, 14, and 16 carbon chain as substituents to produce new amphiphilic kanamycin A dervitives. Although these prepared analogs are less active against bacteria than the parent compound (kanamycin A), some of these derivatives show good antifungal activity especially the compound with &lt;i abp="629"&gt;O-4″ and/or &lt;i abp="630"&gt;O-6″ octyl substitutuants. This family have no toxicity towards mammalian cells in tested concentarations. At the end, the high selectivity is supported by the computational calculations. This work produce antifungal compounds within three simple steps only which make it highly applicable to industry.

Practical and concise synthesizes of antifungal amphiphilic kanamycin analogs

253rd National Meeting (2017)

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