First synthesis of 10α-(trifluoromethyl)deoxoartemisinin

被引:22
作者
Chorki, F
Grellepois, F
Crousse, B
Hoang, VD
Van Hung, N
Bonnet-Delpon, D
Bégué, JP
机构
[1] Ctr Etud Pharmaceut, BioCIS, F-92296 Chatenay Malabry, France
[2] CNST, Inst Chem, Hanoi, Vietnam
关键词
D O I
10.1021/ol017227z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel, nonacetal (trifluoromethyl)deoxoartemisinin was prepared with good stereoselectivity. This compound was obtained by debromination of the 10alpha-CF3-10-bromodeoxoartemisinin in the presence of tributyltin hydride at reflux in toluene without alteration of the endoperoxide bridge. It presented a reasonable antimalarial activity.
引用
收藏
页码:757 / 759
页数:3
相关论文
共 37 条
[21]  
Jung M., 1994, CURR MED CHEM, V1, P35
[22]   A SHORT AND STEREOSPECIFIC SYNTHESIS OF (+)-DEOXOARTEMISININ AND (-)-DEOXODESOXYARTEMISININ [J].
JUNG, MK ;
LI, X ;
BUSTOS, DA ;
ELSOHLY, HN ;
MCCHESNEY, JD .
TETRAHEDRON LETTERS, 1989, 30 (44) :5973-5976
[23]   QINGHAOSU (ARTEMISININ) - AN ANTIMALARIAL DRUG FROM CHINA [J].
KLAYMAN, DL .
SCIENCE, 1985, 228 (4703) :1049-1055
[24]   ANTIMALARIAL ACTIVITY OF NEW WATER-SOLUBLE DIHYDROARTEMISININ DERIVATIVES .2. STEREOSPECIFICITY OF THE ETHER SIDE-CHAIN [J].
LIN, AJ ;
LEE, M ;
KLAYMAN, DL .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1249-1252
[25]   A new synthetic route to 10β-alkyldeoxoartemisinins [J].
Ma, JY ;
Katz, E ;
Ziffer, H .
TETRAHEDRON LETTERS, 1999, 40 (49) :8543-8545
[26]   Syntheses and antimalarial activities of 10-substituted deoxoartemisinins [J].
Ma, JY ;
Katz, E ;
Kyle, DE ;
Ziffer, H .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (22) :4228-4232
[27]   Synthesis and antimalarial activities of fluoroalkyl derivatives of dihydroartemisinin [J].
Nga, TTT ;
Ménage, C ;
Bégué, JP ;
Bonnet-Delpon, D ;
Gantier, JC .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (21) :4101-4108
[28]   Novel, potent, semisynthetic antimalarial carba analogues of the first-generation 1,2,4-trioxane artemether [J].
O'Neill, PM ;
Searle, NL ;
Kan, KW ;
Storr, RC ;
Maggs, JL ;
Ward, SA ;
Raynes, K ;
Park, BK .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (26) :5487-5493
[29]   ACYCLIC STEREOCHEMICAL CONTROL IN FREE-RADICAL REACTIONS [J].
PORTER, NA ;
GIESE, B ;
CURRAN, DP .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (10) :296-304
[30]   Orally active, hydrolytically stable, semisynthetic, antimalarial trioxanes in the artemisinin family [J].
Posner, GH ;
Parker, MH ;
Northrop, J ;
Elias, JS ;
Ploypradith, P ;
Xie, SJ ;
Shapiro, TA .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (02) :300-304