Synthesis and conformational study of 3-hydroxy-4-(hydroxymethyl)-1-cyclohexanyl purines and pyrimidines

被引：65

作者：

Maurinsh, Y

Schraml, J

DeWinter, H

Blaton, N

Peeters, O

Lescrinier, E

Rozenski, J

VanAerschot, A

DeClercq, E

Busson, R

Herdewijn, P

机构：

[1] CATHOLIC UNIV LEUVEN,REGA INST MED RES,B-3000 LOUVAIN,BELGIUM

[2] CATHOLIC UNIV LEUVEN,FAC PHARM,B-3000 LOUVAIN,BELGIUM

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 09期

关键词：

1,5-ANHYDROHEXITOL NUCLEOSIDES; CARBOCYCLIC NUCLEOSIDES; DERIVATIVES; CYCLOHEXENYL; SPECTROSCOPY; SYSTEM; VIRUS;

D O I：

10.1021/jo962204x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclohexane nucleosides with a 1,4-relationship between nucleoside base and hydroxymethyl moiety were synthesized using a conjugated addition reaction of the nucleobases to ethyl 1,3-cyclohexadiene-1-carboxylate and hydroboration of the cyclohexenyl precursor. The lack of antiviral activity of the compounds was correlated with the conformation of these nucleosides as deduced from NMR and X-ray analysis.

引用

页码：2861 / 2871

页数：11

共 40 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2] CYCLOHEXENYL NUCLEOSIDES AND RELATED-COMPOUNDS [J].

ARANGO, JH ;

GEER, A ;

RODRIGUEZ, J ;

YOUNG, PE ;

SCHEINER, P .

NUCLEOSIDES & NUCLEOTIDES, 1993, 12 (07) :773-784

[3]

ARNOTT S, CRC HDB BIOCH, V2, P411

[4]

BERGERHOFF G, 1996, DIAMOND VISUAL STRUC

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

BORTHWICK, AD ;

BIGGADIKE, K .

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

[6] SYNTHESIS AND ANTIVIRAL ACTIVITY OF DIHYDROXYCYCLOHEXYL PYRIMIDINE AND PURINE CARBOCYCLIC NUCLEOSIDES [J].

CALVANI, F ;

MACCHIA, M ;

ROSSELLO, A ;

GISMONDO, MR ;

DRAGO, L ;

FASSINA, MC ;

CISTERNINO, M ;

DOMIANO, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (21) :2567-2572

[7] GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].

CREMER, D ;

POPLE, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358

[8] ABSORPTION-MODE 2-DIMENSIONAL NMR-SPECTRA RECORDED USING PULSED FIELD GRADIENTS [J].

DAVIS, AL ;

LAUE, ED ;

KEELER, J ;

MOSKAU, D ;

LOHMAN, J .

JOURNAL OF MAGNETIC RESONANCE, 1991, 94 (03) :637-644

[9] COMPARATIVE EFFICACY OF ANTIHERPES DRUGS AGAINST DIFFERENT STRAINS OF HERPES-SIMPLEX VIRUS [J].

DECLERCQ, E ;

DESCAMPS, J ;

VERHELST, G ;

WALKER, RT ;

JONES, AS ;

TORRENCE, PF ;

SHUGAR, D .

JOURNAL OF INFECTIOUS DISEASES, 1980, 141 (05) :563-574

[10] 1,5-anhydro-2,3-dideoxy-2-(guanin-9-yl)-D-arabino-hexitol [J].

Declercq, R ;

Herdewijn, P ;

VanMeervelt, L .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 :1213-1215

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