Synthesis of a new nitrogenated drimane derivative with antifungal activity
摘要:
Drimane sesquiterpenes are highly valuable due to their strong biological activity. In this Work, we report the enhanced antifungal activity of 11 -guanidinodrimene, a new compound derived from drimenol. The binding of the guanidine group at the C-I I carbon increased the antifungal activity when tested against Candida albicans, one of the most commonly found human pathogens. (C) 2008 Elsevier Ltd. All rights reserved.
Synthesis of a new nitrogenated drimane derivative with antifungal activity
摘要:
Drimane sesquiterpenes are highly valuable due to their strong biological activity. In this Work, we report the enhanced antifungal activity of 11 -guanidinodrimene, a new compound derived from drimenol. The binding of the guanidine group at the C-I I carbon increased the antifungal activity when tested against Candida albicans, one of the most commonly found human pathogens. (C) 2008 Elsevier Ltd. All rights reserved.
11-Aminodrim-7-ene was synthesized from drimenol in four steps. Drimenol was oxidized into drimenal and its oxime was dehydrated by p-tosylchloride or acetic anhydride in pyridine to form 9-cyano-11-nordrim-7-ene, reduction of which by LiAlH4 in the presence of anhydrous AlCl3 produced 11-aminodrim-7-ene. The reaction of 9-cyano-11-nordrim-7-ene, NaBH4, and CoCl2·6H2O produced a mixture of drimenylamine and 7,8-dihydrodrimenylamine in a 2:1 ratio.