New short route to unsaturated fluoroketonucleosides:: Case of 5-fluoro-1-(6-O-acetyl-3,4-di-deoxy-3-fluoro-β-D-glycero-hex-3-eno-pyranos-2-ulosyl) uracil

被引:5
作者
Egron, MJ
Komiotis, D
Dorange, I
Herscovici, J
Ollapally, AP
Antonakis, K
机构
[1] Ecole Natl Super Chim Paris, CNRS, UMR 8151, F-75005 Paris, France
[2] Univ Thessaly, Dept Biochem & Biotechnol, Larisa, Greece
[3] Florida A&M Univ, Dept Chem, Tallahassee, FL 32307 USA
关键词
D O I
10.1081/NCN-200059683
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The proposed short synthesis involves two key steps: Oxidation of the isopropylidene derivative of the 3 fluoronucleoside possessing a free hydroxyl group in 2-position and acetylation of deprotected 3-fluoro-2-ketonucleoside which, after a beta-elimination reaction, gives the desired unsaturated ketonucleoside 5.
引用
收藏
页码:243 / 246
页数:4
相关论文
共 12 条
[1]   ABSENCE OF GENOTOXIC EFFECTS IN CELLS EXPOSED TO 4 KETONUCLEOSIDE DERIVATIVES [J].
ALAOUIJAMALI, MA ;
LASNE, C ;
ANTONAKIS, K ;
CHOUROULINKOV, I .
MUTAGENESIS, 1986, 1 (06) :411-417
[2]   RELATIONSHIP BETWEEN THE STRUCTURE AND CYTOTOXIC ACTIVITY OF NEW UNSATURATED KETONUCLEOSIDES TESTED ON 8 CELL-LINES [J].
ALAOUIJAMALI, MA ;
EGRON, MJ ;
BESSODES, M ;
ANTONAKIS, K ;
CHOUROULINKOV, I .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1987, 22 (04) :305-310
[3]   NUCLEOSIDE CONFORMATIONS .16. NUCLEAR MAGNETIC-RESONANCE AND CIRCULAR-DICHROISM STUDIES ON PYRIMIDINE-2'-FLUORO-2'-DEOXYRIBONUCLEOSIDES [J].
BLANDIN, M ;
SON, TD ;
CATLIN, JC ;
GUSCHLBAUER, W .
BIOCHIMICA ET BIOPHYSICA ACTA, 1974, 361 (03) :249-256
[4]   Unsaturated fluoroketonucleosides as anticancer agents:: The synthesis and biological activity of 5-fluoro-1-(3,4-di-deoxy-3-fluoro-6-O-trityl-β-D-glycero-hex-3-eno-pyranos-2-ulosyl) uracil [J].
Egron, MJ ;
Dorange, BI ;
Antonakis, K ;
Herscovici, J ;
Ollapally, AP .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2002, 21 (4-5) :327-334
[5]  
EGRON MJ, 1993, CARBOHYD RES, V248, P143
[6]   BIOLOGICALLY IMPORTANT NUCLEOSIDES - A GENERAL-METHOD FOR THE SYNTHESIS OF UNSATURATED KETONUCLEOSIDES OF URACIL AND ITS ANALOGS [J].
KOMIOTIS, D ;
DELATRE, S ;
HOLT, L ;
OLLAPALLY, AP ;
BALZARINI, J ;
DECLERCQ, E ;
IIGO, M .
NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (1-3) :431-455
[7]   DIRECT FLUORINATION AT POSITION-3', POSITION-4', AND POSITION-6' OF BETA-D-GLUCOPYRANOSYLTHEOPHYLLINE [J].
LECLERCQ, F ;
ANTONAKIS, K .
CARBOHYDRATE RESEARCH, 1989, 193 :307-313
[8]   A COMPARATIVE CONFORMATIONAL STUDY OF CERTAIN 2'-DEOXY-2'-FLUORO-ARABINOFURANOSYLCYTOSINE NUCLEOSIDES [J].
LIPNICK, RL ;
FISSEKIS, JD .
BIOCHIMICA ET BIOPHYSICA ACTA, 1980, 608 (01) :96-102
[9]   STRUCTURE OF NUCLEOCIDIN .3. (A NEW STRUCTURE) [J].
MORTON, GO ;
LANCASTER, JE ;
VANLEAR, GE ;
FULMOR, W ;
MEYER, WE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (06) :1535-+
[10]   5-fluoro-1-(3,4-dideoxy-3-fluoro-6-0-trityl-beta-D- glycero-hex-3-eno-pyranos-2-ulosyl (uracil): Anticancer agent [J].
Ollapally, AP ;
Bennouna-Dorange, I ;
Whitaker, TL .
NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (4-5) :703-705