The cyclohexene ring as bioisostere of a furanose ring: Synthesis and antiviral activity of cyclohexenyl nucleosides

被引:48
作者
Herdewijn, P
De Clercq, E
机构
[1] Katholieke Univ Leuven, Rega Inst Med Res, Med Chem Lab, B-3000 Louvain, Belgium
[2] Katholieke Univ Leuven, Rega Inst Med Res, Lab Antiviral Chemotherapy, B-3000 Louvain, Belgium
关键词
D O I
10.1016/S0960-894X(01)00270-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The application of the bioisosteric concept between a furanose ring and a cyclohexene ring in the nucleoside field has led to the discovery of new potent antiviral agents. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:1591 / 1597
页数:7
相关论文
共 16 条
[1]   ON THE POTENTIAL-ENERGY SURFACE FOR RING INVERSION IN CYCLOHEXENE AND RELATED MOLECULES [J].
ANET, FAL ;
FREEDBERG, DI ;
STORER, JW ;
HOUK, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10969-10971
[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]   GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].
CREMER, D ;
POPLE, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358
[4]  
Cremer D., 1995, CONFORMATIONAL BEHAV, P59
[5]  
DECLERCQ E, 2000, IN PRESS NUCL NUCL N
[6]   Synthesis of nucleosides and related compounds .38. Deamination of 9-(hydroxymethylated cycloalkyl)-9H-adenines (carbocyclic adenine nucleosides) by adenosine deaminase: Effect of high-pressure upon deamination rate and enantioselectivity [J].
Katagiri, N ;
Ito, Y ;
Shiraishi, T ;
Maruyama, T ;
Sato, Y ;
Kaneko, C .
NUCLEOSIDES & NUCLEOTIDES, 1996, 15 (1-3) :631-647
[7]   Cyclohexenyl nucleosides: Synthesis of cis-4-(9H-purin-9-yl)-2-cyclohexenylcarbinols. [J].
Konkel, MJ ;
Vince, R .
TETRAHEDRON, 1996, 52 (03) :799-808
[8]   Cyclohexenyl nucleosides: Synthesis and biological activity of trans-3-(purin-9-yl)-4-cyclohexenylcarbinols [J].
Konkel, MJ ;
Vince, R .
TETRAHEDRON, 1996, 52 (27) :8969-8978
[9]   Synthesis and biological activity of cyclohexenyl nucleosides. cis-5-(9H-purin-9-yl)-3-cyclohexenyl carbinols and their 8-azapurinyl analogs [J].
Konkel, MJ ;
Vince, R .
NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (9-10) :2061-2077
[10]   Synthesis and conformational study of 3-hydroxy-4-(hydroxymethyl)-1-cyclohexanyl purines and pyrimidines [J].
Maurinsh, Y ;
Schraml, J ;
DeWinter, H ;
Blaton, N ;
Peeters, O ;
Lescrinier, E ;
Rozenski, J ;
VanAerschot, A ;
DeClercq, E ;
Busson, R ;
Herdewijn, P .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2861-2871