SYNTHETIC APPROACHES TOWARDS NUCLEOCIDIN AND SELECTED ANALOGS - ANTI-HIV ACTIVITY IN 4'-FLUORINATED NUCLEOSIDE DERIVATIVES

被引：38

作者：

MAGUIRE, AR

MENG, WD

ROBERTS, SM

WILLETTS, AJ

机构：

[1] UNIV EXETER,DEPT CHEM,EXETER EX4 4RJ,DEVON,ENGLAND

[2] UNIV EXETER,DEPT BIOL SCI,EXETER EX4 4RJ,DEVON,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 15期

关键词：

D O I：

10.1039/p19930001795

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleocidin 1 has been synthesised from the adenosine derivative 4 via the intermediacy of the dihalogeno compound 9. The latter compound showed slight but significant activity against HIV-infected cells while the isomer 10 and the monohalogeno compound 60 were inactive. Synthetic approaches towards other 4'-fluorinated nucleoside derivatives are also described. The epimeric 4'-fluorinated nucleosides 26 and 27 displayed similar activity against HIV-infected cells to that observed for the dihalogenated compound 9.

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页码：1795 / 1808

页数：14

相关论文

共 33 条

[1] SYNTHESIS AND INTERACTION WITH URIDINE PHOSPHORYLASE OF 5'-DEOXY-4',5-DIFLUOROURIDINE, A NEW PRODRUG OF 5-FLUOROURACIL [J].

AJMERA, S ;

BAPAT, AR ;

STEPHANIAN, E ;

DANENBERG, PV .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (06) :1094-1098

[2]

BACKUS E. J., 1957, ANTIBIOT AND CHEMOTHER, V7, P532

[3] 4'-MODIFICATION OF CARBOCYCLIC NUCLEOSIDES - SYNTHESIS OF 4'-ALPHA-FLUORO, 4'-ALPHA-HYDROXY AND 4',6'-UNSATURATED DERIVATIVES OF THE ANTIVIRAL AGENT 2'-ARA-FLUORO CARBOCYCLIC GUANOSINE [J].

BIGGADIKE, K ;

BORTHWICK, AD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (19) :1380-1382

[4]

BLANK HU, 1970, LIEBIGS ANN CHEM, V742, P34

[5] IMPROVED OXIDATION PROCEDURE WITH AROMATIC PEROXYACIDS [J].

CAMPS, F ;

COLL, J ;

MESSEGUER, A ;

PERICAS, MA .

TETRAHEDRON LETTERS, 1981, 22 (39) :3895-3896

[6] META-CHLOROPEROXYBENZOIC ACID POTASSIUM FLUORIDE SYSTEM - STUDY OF ITS STABILITY AND REACTION WITH ALPHA-METHYLSTYRENE [J].

CAMPS, F ;

COLL, J ;

MESSEGUER, A ;

PUJOL, F .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (27) :5402-5404

[7] SYNTHESIS OF 9-[5-(ALKYLTHIO)-5-DEOXY-BETA-D-ERYTHRO-PENT-4-ENOFURANOSYL)ADENINES AS POTENTIAL INHIBITORS OF TRANSMETHYLATION [J].

CRAIG, GW ;

STERNBERG, ED ;

JONES, GH ;

MOFFATT, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (08) :1258-1264

[8] HALO SUGAR NUCLEOSIDES .6. SYNTHESIS OF SOME 5'-DEOXY-5'-IODO AND 4',5'-UNSATURATED PURINE NUCLEOSIDES [J].

DIMITRIJEVICH, SD ;

VERHEYDEN, JPH ;

MOFFATT, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (03) :400-406

[9]

EVANS RD, 1987, SYNTHESIS-STUTTGART, P551

[10] UMSETZUNGEN MIT N-CARBONYL-SULFAMIDSAURE-CHLORID .1. UBER DAS SULFAMIDSAURECHLORID [J].

GRAF, R .

CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (02) :509-513

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