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

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...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2001-09, Vol.64 (9), p.1201-1205
Main Authors: Han, Jaehong, Lee, Jung-Gul, Min, Sun-Sik, Park, Si-Hyung, Angerhofer, Cindy K, Cordell, Geoffrey A, Kim, Soo-Un
Format: Article
Language:English
Subjects:
Animals
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antimalarials - chemical synthesis
Antimalarials - chemistry
Antimalarials - pharmacology
Antiparasitic agents
Artemisinins
Biological and medical sciences
Chloroquine - pharmacology
Chromatography, Thin Layer
Drug Resistance, Microbial
Drugs, Chinese Herbal - chemical synthesis
Drugs, Chinese Herbal - chemistry
Drugs, Chinese Herbal - pharmacology
Gas Chromatography-Mass Spectrometry
Humans
In Vitro Techniques
KB Cells
Magnetic Resonance Spectroscopy
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
Plasmodium
Plasmodium falciparum - drug effects
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Spectrophotometry, Infrared
Spectroscopy, Fourier Transform Infrared
Stereoisomerism
Structure-Activity Relationship
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Description
Summary: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).
ISSN:0163-3864
1520-6025
DOI:10.1021/np0101752