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Molecules 2003, 8(12), 901-909; doi:10.3390/81200901

New Bioactive Azaartemisinin Derivatives

1, 1,2, 1, 1,2 and 1,*
1 Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia 2 Current address:Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Kasr El-Eini, Cairo 11562, Egypt
* Author to whom correspondence should be addressed.
Received: 19 February 2003 / Revised: 5 October 2003 / Accepted: 24 November 2003 / Published: 31 December 2003
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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.
Keywords: Artemisinin; azaartemisinin derivatives; bioactivity; NMR Artemisinin; azaartemisinin derivatives; bioactivity; NMR
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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