New Method for the Synthesis of Ether Derivatives of Artemisinin

REFERENCES

• (a) Liu , Y. ; Wong , V. K.-W. ; Ko , B. C.-B. ; Wong , M.-K. ; Che , C.-M. Synthesis and cytotoxicity studies of artemisinin derivatives containing lipophilic alkyl carbon chains. Org. Lett. 2005, 7, 1561–1564; (b) Schnur , R. C. ; Corman , M. L. ; Gallaschun , R. J. ; Cooper , B. A. ; Dee , M. F. ; Doty , J. L. ; Mumi , M. L. ; DiOrio , C. I. ; Barbacci , E. G. ; Miller , P. E. ; Pollack , V. A. ; Savage , D. M. ; Sloan , D. E. ; Pustilnik , L. R. ; Moyer , J. D. ; Moyer , M. P. erbB-2 Oncogene inhibition by geldanamycin derivatives: Synthesis, mechanism of action, and structure–activity relationships. J. Med. Chem. 1996, 38, 3813–3820; (c) Deutsch , H. M. ; Glinski , J. A. ; Hernandez , M. ; Haugwitz , R. D. ; Narayanan , V. L. ; Suffness , M. ; Zalkow , L. H. Synthesis of congeners and prodrugs, 3: Water-soluble prodrugs of taxol with potent antitumor activity. J. Med. Chem. 1989, 32, 788–792; (d) Mangatal , L. ; Adeline , M. T. ; Gumnard , D. ; Gueritte-Voedelein , F. ; Potier , P. Application of the vicinal oxyamination reaction with asymmetric induction to the hemisynthesis of taxol and analogues. Tetrahedron 1989, 45, 4177–4190; (e) Cheng , K. L. ; Bradley , T. ; Budman , D. R. Novel microtubule-targeting agents: The epothilones. Biologics: Targets Ther. 2008, 2, 789–811.
   PubMed Web of Science ®Google Scholar
• For reviews on artemisinin and its derivatives, see (a) Klayman , D. L. Qinghaosu (artemisinin): An antimalarial drug from China . Science 1985 , 228 , 1049 – 1055 ; (b) Luo , X. D. ; Shen , C. C. The chemistry, pharmacology, and clinical applications of qinghaosu (srtemisinin) and its derivatives . Med. Res. Rev. 1987 , 7 , 29 – 52 ; (c) Zaman , S. S. ; Sharma , R. P. Some aspect of chemistry and biological activity of artemisenin and related antimalarials . Heterocycles 1991 , 32 , 1593 – 1637 ; (d) Butler , A. R. ; Wu , Y. L. Artemisinin (qinghaosu): A new type of antimalarial drug . Chem. Soc. Rev. 1992 , 21 , 85 – 90 ; (e) Meshnick , S. R. ; Taylor , T. E. ; Kamchonwongpaisan , S. Artemisinin and the antimalarial endoperoxides: From herbal remedy to targeted chemotherapy . Microbiol. Rev. 1996 , 60 , 301 – 315 ; (f) Haynes , R. K. ; Vonwiller , S. C. From qinghao, marvelous herb of antiquity, to the antimalarial trioxane qinghaosu and some remarkable new chemistry . Acc. Chem. Res. 1997 , 30 , 73 – 79 ; (g) Bhattacharya , A. K. ; Sharma , R. P. Recent developments in the chemistry and biological activity of artemisinin and related antimalarials–an update . Heterocycles 1999 , 51 , 1681 – 1745 ; (h) Chaturvedi , D. ; Goswami , A. ; Saikia , P. P. ; Barua , N. C. ; Rao , P. G. Artemisinin and its derivatives: A novel class of antimalarial and anticancer agents . Chem. Soc. Rev. 2010 , 39 , 435 – 454 .
   PubMed Web of Science ®Google Scholar
• China Co-operative Research Group on Qinghouso and Its Derivatives as Antimalarials . The chemistry and synthesis of qinghaosu derivatives . J. Tradit. Chin. Med. 1982 , 2 , 9 – 16 .
   PubMedGoogle Scholar
• (a) China Co-operative research group on Qinghouso and its derivatives as antimalarials . Metabolism and pharmacokinetics of qinghaosu and its derivatives . J. Tradit. Chin. Med. 1982 , 2 , 25 – 30 ; (b) Lee , I. K. ; Mufford , C. D. Metabolism of antimalarial sesquiterpene lactones . Pharmacol. Ther. 1990 , 48 , 345 – 355 .
   PubMedGoogle Scholar
• (a) China Co-operative Research Group on Qinghouso and Its Derivatives as Antimalarials . Clinical studies on the treatment of malaria with qinghaosu and its derivatives . J. Tradit. Chin. Med. 1982 , 2 , 45 – 50 ; (b) Titulaer , H. A. C. ; Zuidema , Z. ; Lugt , C. B. Formulation and pharmacokinetics of artemisinin and its derivatives . Int. J. Pharm. 1991 , 69 , 83 – 92 ; (c) Giao , P. T. ; Binh , T. Q. ; Kager , P. A. ; Long , H. P. ; Van Thang , N. ; Van Nam , N. ; de Vries , P. J. Artemisinin for treatment of uncomplicated falciparum malaria: Is there a place for monotherapy? Am. J. Trop. Med. Hyg. 2001 , 65 , 690 – 695 .
   PubMedGoogle Scholar
• (a) Li , Y. ; Yu , P.-L. ; Chen , Y.-X. ; Li , L.-Q. ; Gai , Y.-Z. ; Wang , D. S. ; Zheng , Y.-P. Synthesis of ethers, carboxylic esters and carbonates of dihydroarthemisinin . Acta Pharm. Sin. 1981 , 16 , 429 – 439 ; (b) Wang , T. Y. ; Xu , R. C. Clinical studies of treatment of falciparum malaria with artemether, a derivative of qinghaosu . J. Tradit. Chin. Med. 1985 , 5 , 240 – 242 .
   Google Scholar
• Boehm , M. ; Fuenfschilling , P. C. ; Krieger , M. ; Kuesters , E. ; Struber , F. An improved manufacturing process for the antimalaria drug coartem: part II . Org. Process Res. Dev. 2007 , 11 , 336 – 340 .
   Web of Science ®Google Scholar
• El-Feraly , F. S. ; Al-Vahya , M. A. ; Oribi , K. V. ; McPhail , D. R. ; McPhail , A. T. A new method for the preparation of arteether and its C-9 epimer . J. Nat. Prod. 1992 , 55 , 878 – 883 .
   Web of Science ®Google Scholar
• (a) Lin , A. J. ; Klayman , D. L. ; Milhous , W. K. Antimalarial activity of a new water-soluble dihydroartemisinin derivative . J. Med. Chem. 1987 , 30 , 2147 – 2150 ; (b) Brossi , A. ; Venugopalan , B. ; Dominguez Gerpe , L. ; Yeh , H. J. C. ; Flippen-Anderson , J. L. ; Buchs , P. ; Luo , X. D. ; Milhous , W. ; Peters , W. Arteether, a new antimalarial drug: Synthesis and antimalarial properties . J. Med. Chem. 1988 , 31 , 645 – 650 .
   PubMed Web of Science ®Google Scholar
• Bhakuni , R. S. ; Jain , D. C. ; Sharma , R. P. An improved procedure for the synthesis of ethers of dihydroartemisinin. Ind. J. Chem. 1995, 34B, 529–530.
   Google Scholar
• Singh , C. ; Tiwari , P. A one-pot conversion of artemisinin to its ether derivatives . Tetrahedron Lett. 2002 , 43 , 7235 – 7237 .
   Web of Science ®Google Scholar
• (a) Kozhevnikov , I. V. Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions . Chem. Rev. 1998 , 98 , 171 – 198 ; (b) Briand , L. E. ; Baronetti , G. T. ; Thomas , H. J. The state of the art on Wells: Dawson heteropoly-compounds. A review of their properties and applications . Appl. Catal. A 2003 , 256 , 37 – 50 ; (c) Timofeeva , M. N. Acid catalysis by heteropoly acids . Appl. Catal. A 2003 , 256 , 19 – 35 ; (d) Firouzabadi , B. ; Iranpoor , N. ; Jafari , A. A. H3PW12O40 as a useful recyclable heterogeneous catalyst for the facile and highly efficient Michael addition reaction of thiols to α,β-unsaturated ketones . Synlett 2005 , 299 – 303 .
   PubMed Web of Science ®Google Scholar
• (a) Brewer , T. G. ; Peggins , J. O. ; Grate , S. J. ; Petras , J. M. ; Levine , B. S. ; Weina , P. J. ; Swearengen , J. ; Heiffer , M. H. ; Schuster , B. G. Neurotoxicity in animals due to arteether and artemether . Trans. R. Soc. Trop. Med. Hyg. 1994 , 88 , 33 – 36 ; (b) Brewer , T. G. ; Genovese , R. F. ; Newman , D. B. ; Li , Q. Factors relating to neurotoxicity of artemisinin antimalarial drugs “listening to arteether .” Med. Trop. 1998 , 58 , 22S – 27S ; (c) Li , Q.-G. ; Peggins , J. O. ; Lin , A. J. ; Masonic , K. J. ; Trotman , K. M. ; Brewer , T. G. Pharmacology and toxicology of artelinic acid: Preclinical investigations on pharmacokinetics, metabolism, protein and red blood cell binding, and acute and anorectic toxicities . Trans. R. Soc. Trop. Med. Hyg. 1998 , 92 , 332 – 340 .
   PubMed Web of Science ®Google Scholar