Functionalisation of artemisinin and its ring-contracted derivatives

Molecules

Volumn 12, Issue 3, 2007, Pages 395-405

  Van Neck, Tine ^a   Van Mierloo, Sarah ^a   Dehaen, Wim ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

1,3 dipolar cycloaddition; Aldehyde; Artemisinin; Nitrile oxide; Ring contraction

Indexed keywords

ARTEMISININ; ARTEMISININ DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMISTRY; SYNTHESIS;

ARTEMISININS; HETEROCYCLIC COMPOUNDS;

EID: 34147142283     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12030395     Document Type: Article

References (11)

1. For recent review articles on artemisinin and its derivatives see: (a) Kim B.J.; Sasaki, T. Recent progress in the synthesis of artemisinin and its derivatives Org. Prep. Proced. Int. 2006, 38, 1-80;
2. (b) Jung, M.; Lee, K., Kim, H, Park, M. Recent advances in artemisinin and its derivatives as antimalarial and antitumor agents. Current Med. Chem. 2004, 11, 1265-1284;
3. (c) van Agtmael, M. A.; Eggelte, T. A.; van Boxtel C. J. Artemisinin drugs in the treatment of malaria : from medicinal herb to registered medication Trends Pharm. Sci. 1999, 20, 199-205.
4. Hindley, S.; Ward, S. A.; Storr, R. C.; Searle, N. L.; Bray, P. G.; Park, B. K.; Davies, J.; O'Neill, P. M. Mechanism-based design of parasite-targeted artemisinin derivatives: synthesis and antimalarial activity of new diamine containing analogues. J. Med. Chem. 2002, 45, 1052-1063.
5. (a) Grellepois, F.; Bonnet-Delpon, D.; Bégué, J.-P. Ring-contracted artemisinin derivatives: stereoselective reaction of anhydrodihydroartemisinin towards halogenation reagents. Tetrahedron Lett. 2001, 42, 2125-2127;
6. (b) Grellepois, F.; Chorki, F. Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D.; Bégué, J.-P. Anhydrodihydroartemisin and its 10-trifluoromethyl analogue: access to novel D-ring-contracted artemisinin trifluoromethyl ketones J. Org. Chem. 2002, 67, 1253-1260.
7. (a) Lee, G.A. A simplified synthesis of unsaturated nitrogen heterocycles using nitrilium betaines Synthesis 1982, 508-509;
8. L'abbé, G.; Emmers, S.; Dehaen, W.; Dyall, L. 5-Chloropyrazole-4- carbaldehydes as synthons for intramolecular 1,3-dipolar cycloadditions, J. Chem. Soc. Perkin Trans 1 1994, 2553-2558.
9. For a few recent examples see: (a) Liu, Y.; Wong, V. K.-W.; Ko, B. C.-B.;Wong, M.-K.; Che, C.-M. Synthesis and cytotoxic study of artemisinin derivatives containing lipophilic alkyl carbon chains Org. Lett. 2005, 7, 1561-1564;
10. (b) Ma, J.; Katz, E.; Kyle, D. E.; Ziffer, H. Syntheses and antimalarial activities of 10-substituted deoxoartemisinins J. Med. Chem. 2000, 43, 4228-4232.
11. Venugopalan, B.; Bapat, C. P.; Karnik, P. J.; Chatterjee, D. K.; Iyer, N.; Lepcha, D. Antimalarial activity of novel ring-contracted artemisinin derivatives. J. Med. Chem. 1995, 38, 1922