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

Authors
Han, JH Lee, JG Min, SS Park, SH Angerhofer, CK Cordell, GA Kim, SU
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).