Synthesis of New Artemisinin Analogues from Artemisinic Acid Modified at C-3 and C-13 and Their Antimalarial Activity

Journal of Natural Products
2001.0

Abstract

Artemisinic acid (2) was modified through allylic oxidation at C-3 or conjugate addition at C-13 to afford 12 methyl artemisinate derivatives (4-15). Photooxidation of the derivatives yielded eight new artemisinin analogues, including 13-cyanoartemisinin (16), 13-methoxycarbonyl artemisinin (17), 13-methoxyartemisinin (18), 13-ethylsulfonylartemisinin (19), 13-nitromethylartemisinin (20), 13-(1-nitroethyl)artemisinin (21), (3R)-3-hydroxyartemisinin (22), and (3R)-3-acetoxyartemisinin (23). Among the analogues, only compound 20 had antimalarial activity comparable to artemisinin (1).

Knowledge Graph

Similar Paper

Synthesis of New Artemisinin Analogues from Artemisinic Acid Modified at C-3 and C-13 and Their Antimalarial Activity
Journal of Natural Products 2001.0
Structure−Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and In Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates
Journal of Medicinal Chemistry 2002.0
Antimalarial activities of (+)-deoxoartemisitene and its novel C-11, 13 derivatives
Bioorganic & Medicinal Chemistry Letters 2004.0
Mechanism-Based Design of Parasite-Targeted Artemisinin Derivatives:  Synthesis and Antimalarial Activity of Benzylamino and Alkylamino Ether Analogues of Artemisinin
Journal of Medicinal Chemistry 1996.0
Structure−Activity Relationships of the Antimalarial Agent Artemisinin. 8. Design, Synthesis, and CoMFA Studies toward the Development of Artemisinin-Based Drugs against Leishmaniasis and Malaria
Journal of Medicinal Chemistry 2003.0
Synthesis, antimalarial activity and cytotoxicity of 10-aminoethylether derivatives of artemisinin
Bioorganic & Medicinal Chemistry 2012.0
Antifungal Activity of Artemisinin Derivatives
Journal of Natural Products 2005.0
Orally Active, Hydrolytically Stable, Semisynthetic, Antimalarial Trioxanes in the Artemisinin Family
Journal of Medicinal Chemistry 1999.0
Synthesis and biological evaluation of a series of non-hemiacetal ester derivatives of artemisinin
European Journal of Medicinal Chemistry 2016.0
Synthesis, Stability, and Antimalarial Activity of New Hydrolytically Stable and Water-Soluble (+)-Deoxoartelinic Acid
Journal of Medicinal Chemistry 2002.0