Synthesis of new artemisinin analogues from artemisinic acid modified at C-3 and C-13 and their antimalarial activity

Citation
Jh. Han et al., Synthesis of new artemisinin analogues from artemisinic acid modified at C-3 and C-13 and their antimalarial activity, J NAT PROD, 64(9), 2001, pp. 1201-1205
Citations number
26
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Agricultural Chemistry","Pharmacology & Toxicology
Journal title
JOURNAL OF NATURAL PRODUCTS
ISSN journal
0163-3864 → ACNP
Volume
64
Issue
9
Year of publication
2001
Pages
1201 - 1205
Database
ISI
SICI code
0163-3864(200109)64:9<1201:SONAAF>2.0.ZU;2-H
Abstract
Artemisinic acid (2) was modified through allylic oxidation at C-3 or conju gate 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-nitromethyla rtemisinin (20), 13-(1-nitroethyl)artemisinin (21), (3R)-3-hydroxyartemisin in (22), and (3R)-3-acetoxyartemisinin (23). Among the analogues, only comp ound 20 had antimalarial activity comparable to artemisinin (1).