Abstract: Reaction of artemisinin (1) with ethanolamine, followed by acid treatment produced the lactam (4S,8S,9S,13S,1R,5R,12R)-11-aza-11-(2-hydroxyethyl)-1,5,9-trimethyl-14,15-dioxatetracyclo [10.2.1.0<4,13>.0<8,13>]pentadecan-10-one (4) and the diol (1S,2S,6S,7S,5R,8R)-4-aza-5,6-dihydroxy-4-(2-hydroxyethyl)-2,8-dimethyl-7-(3-oxobutyl) bicyclo[4.4.0]decan-3-one (7). When ethylenediamine was used instead of the ethanolamine, the dimeric lactam (1S,4S,8S,9S,13S,5R,12R)-11-[2-((1S,4S,8S,9S,13S,5R,12R)-11-aza-1,5,9-trimethyl-14,15-dioxa-10-oxotetracyclo[10.2.1.0<4,13>.0<8,13>] pentadec-11-yl)ethyl]-11-aza-1,5,9-tri-methyl-14,15-dioxatetracyclo-[10.2.1.0<4,13>.0<8,13>]-pentadecan-10-one (8) was obtained. All compounds are new azaartemisinin derivatives lacking the peroxide functionality. These compounds were evaluated for antimalarial and cytotoxic activities. Only the dimer 8 was found to possess antimalarial activity, while only the diol 7 exhibited cytotoxic activity against human breast ductal carcinoma.
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Al-Oqail, M.M.; Galal, A.M.; Ahmad, M.S.; Al-Fishawi, A.M.; El-Feraly, F.S. New Bioactive Azaartemisinin Derivatives. Molecules 2003, 8, 901-909.
Al-Oqail MM, Galal AM, Ahmad MS, Al-Fishawi AM, El-Feraly FS. New Bioactive Azaartemisinin Derivatives. Molecules. 2003; 8(12):901-909.
Al-Oqail, Mai M.; Galal, Ahmed M.; Ahmad, Mohamed S.; Al-Fishawi, Ahlam M.; El-Feraly, Farouk S. 2003. "New Bioactive Azaartemisinin Derivatives." Molecules 8, no. 12: 901-909.