Synthesis of 11-aza-artemisinin derivatives using the Ugi reaction and an evaluation of their antimalarial activity

Thanh Nguyen Le,; De Borggraeve, Wim; Grellier, Philippe; Van Cuong Pham,; Dehaen, Wim; Van Hung Nguyen,

doi:10.1016/j.tetlet.2014.07.027

Synthesis of 11-aza-artemisinin derivatives using the Ugi reaction and an evaluation of their antimalarial activity

Author:

Thanh Nguyen Le,

De Borggraeve, Wim ; Grellier, Philippe ; Van Cuong Pham, ; Dehaen, Wim ; Van Hung Nguyen,

Keywords:

Artemisinin, Aza-artemisinin, Ugi reaction, Antimalarial, Synthesis, Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, MULTICOMPONENT REACTIONS, 11-AZAARTEMISININ, ARTEMISININ, ADDUCTS, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3101 Biochemistry and cell biology, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

© 2014 Elsevier Ltd. All rights reserved. A series of new 11-aza-artemisinin derivatives were prepared from 11-aza-artemisinin using the Ugi reaction. An antimalarial activity evaluation against the FcB1 strain indicated that compounds 7, 10, and 16 had very strong inhibitory activity. Comparison of the activity among the synthetic derivatives of this series revealed that the length of the side chain R group on the amide nitrogen could be critical for their antimalarial properties.