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Open AccessArticle

New Bioactive Azaartemisinin Derivatives

Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Current address:Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Kasr El-Eini, Cairo 11562, Egypt
Author to whom correspondence should be addressed.
Molecules 2003, 8(12), 901-909;
Received: 19 February 2003 / Revised: 5 October 2003 / Accepted: 24 November 2003 / Published: 31 December 2003
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 [<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[<4,13>.0<8,13>] pentadec-11-yl)ethyl]-11-aza-1,5,9-tri-methyl-14,15-dioxatetracyclo-[<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. View Full-Text
Keywords: Artemisinin; azaartemisinin derivatives; bioactivity; NMR Artemisinin; azaartemisinin derivatives; bioactivity; NMR
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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.

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