SYNTHESIS OF A NEW EXOCYCLIC AMINO CARBOCYCLIC NUCLEOSIDE WITH POTENTIAL ANTIVIRAL ACTIVITY

被引：11

作者：

AGROFOGLIO, L

CONDOM, R

GUEDJ, R

CHALLAND, R

SELWAY, J

机构：

[1] Lab. Chimie Bio-Organique. Université de Nice - Sophia Antipolis, Faculté des Sciences, 06108 Nice

[2] Wellcome Research Laboratories, Beckenham,, Kent Kent BR3 3BS, Langley Court

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 39期

关键词：

D O I：

10.1016/S0040-4039(00)73729-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of a new exocyclic amino carbocyclic nucleoside, (+/-)-1, (+/-)-1-(beta)-[4-(6-amino-5-nitro)pyrimidine]-amino-2-(alpha)-hydroxy-4'-hydroxymethylcyclopentane has been accomplished. 1-Hydroxymethyl-3-cyclopentene has been converted into a carbocyclic nucleoside in six steps.

引用

收藏

页码：6271 / 6272

页数：2

相关论文

共 22 条

[1] STERIC CONTROL OF THE EPOXIDATION OF 1-HYDROXYMETHYL-3-CYCLOPENTENE USING ARYL OR SILYL HYDROXYL PROTECTING GROUPS [J].

AGROFOGLIO, L ;

CONDOM, R ;

GUEDJ, R .

TETRAHEDRON LETTERS, 1992, 33 (38) :5503-5504

[2] FLUORO CARBOCYCLIC NUCLEOSIDES - SYNTHESIS AND ANTIVIRAL ACTIVITY OF 2'-FLUORO AND 6'-FLUORO CARBOCYCLIC PYRIMIDINE NUCLEOSIDES INCLUDING CARBOCYCLIC 1-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)-5-METHYLURACIL AND CARBOCYCLIC 1-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)-5-IODOURACIL [J].

BORTHWICK, AD ;

EVANS, DN ;

KIRK, BE ;

BIGGADIKE, K ;

EXALL, AM ;

YOUDS, P ;

ROBERTS, SM ;

KNIGHT, DJ ;

COATES, JAV .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :179-186

[3] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].

BORTHWICK, AD ;

BIGGADIKE, K .

TETRAHEDRON, 1992, 48 (04) :571-623

[4] SYNTHESIS AND ENZYMATIC RESOLUTION OF CARBOCYCLIC 2'-ARA-FLUORO-GUANOSINE - A POTENT NEW ANTI-HERPETIC AGENT [J].

BORTHWICK, AD ;

BUTT, S ;

BIGGADIKE, K ;

EXALL, AM ;

ROBERTS, SM ;

YOUDS, PM ;

KIRK, BE ;

BOOTH, BR ;

CAMERON, JM ;

COX, SW ;

MARR, CLP ;

SHILL, MD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) :656-658

[5] BROAD-SPECTRUM ANTIVIRAL AND CYTOCIDAL ACTIVITY OF CYCLOPENTENYLCYTOSINE, A CARBOCYCLIC NUCLEOSIDE TARGETED AT CTP SYNTHETASE [J].

DECLERCQ, E ;

MURASE, J ;

MARQUEZ, VE .

BIOCHEMICAL PHARMACOLOGY, 1991, 41 (12) :1821-1829

[6]

FEEYA D, 1981, J ORG CHEM, V46, P3512

[7] TOTAL SYNTHESIS OF (-)-NEPLANOCIN A1 [J].

LIM, MI ;

MARQUEZ, VE .

TETRAHEDRON LETTERS, 1983, 24 (50) :5559-5562

[8] CARBOCYCLIC NUCLEOSIDES [J].

MARQUEZ, VE ;

LIM, MI .

MEDICINAL RESEARCH REVIEWS, 1986, 6 (01) :1-40

[9]

MONTGOMERY JA, 1982, MED RES REV, V2, P271, DOI 10.1002/med.2610020304

[10] SYNTHESIS, INTRAMOLECULAR HYDROGEN-BONDING, AND BIOCHEMICAL-STUDIES OF CLITOCINE, A NATURALLY-OCCURRING EXOCYCLIC AMINO NUCLEOSIDE [J].

MOSS, RJ ;

PETRIE, CR ;

MEYER, RB ;

NORD, LD ;

WILLIS, RC ;

SMITH, RA ;

LARSON, SB ;

KINI, GD ;

ROBINS, RK .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (04) :786-790