Synthesis, antiviral and cytostatic activities, of carbocyclic nucleosides incorporating a modified cyclopentane ring.: IV.: Adenosine and uridine analogues

被引：27

作者：

Nieto, MI

Caamaño, O

Fernández, F

Gómez, M

Balzarini, J

De Clercq, E

机构：

[1] Univ Santiago, Fac Farm, Dept Quim Organ, E-15782 Santiago De Compostela, Spain

[2] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2002年 / 21卷 / 03期

关键词：

D O I：

10.1081/NCN-120003289

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：

Eight new carbocyclic nucleosides were prepared by mounting a purine (compounds 8-10), 8-azapurine (12 and 13) or pyrimidine (15, 16 and 17b) on the amino group of (1S,3R)-3-aminomethyl-2,2,3-trimethyl-cyclopentylmethanol (6). All the compounds were evaluated as antiviral and antitumor agents in a variety of assay systems. Only compound 8 showed any cytostatic activity against the tumor cell lines examined.

引用

收藏

页码：243 / 255

页数：13

相关论文

共 24 条

[1] SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].

AGROFOGLIO, L ;

SUHAS, E ;

FARESE, A ;

CONDOM, R ;

CHALLAND, SR ;

EARL, RA ;

GUEDJ, R .

TETRAHEDRON, 1994, 50 (36) :10611-10670

[2] Synthesis and antiviral and cytostatic activities of carbocyclic nucleosides incorporating a modified cyclopentane ring .1. Guanosine analogues. [J].

Blanco, JM ;

Caamano, O ;

Fernandez, F ;

Gomez, G ;

Nieto, MI ;

Balzarini, J ;

Padalko, E ;

DeClercq, E .

NUCLEOSIDES & NUCLEOTIDES, 1997, 16 (1-2) :159-171

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

BORTHWICK, AD ;

BIGGADIKE, K .

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

[4] SYNTHESIS OF (1R,CIS)-3-AMINOMETHYL-1,2,2-TRIMETHYLCYCLOPENTANE-METHANOL - 2 APPROACHES USING ALPHA-CAMPHIDONE [J].

CAAMANO, O ;

FERNANDEZ, F ;

GOMEZ, G ;

NIETO, I .

TETRAHEDRON, 1994, 50 (07) :2175-2182

[5] An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen® (1592U89) [J].

Daluge, SM ;

Martin, MT ;

Sickles, BR ;

Livingston, DA .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2000, 19 (1-2) :297-327

[6] 1592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity [J].

Daluge, SM ;

Good, SS ;

Faletto, MB ;

Miller, WH ;

StClair, MH ;

Boone, LR ;

Tisdale, M ;

Parry, NR ;

Reardon, JE ;

Dornsife, RE ;

Averett, DR ;

Krenitsky, TA .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (05) :1082-1093

[7]

Fernández F, 2001, SYNTHESIS-STUTTGART, P239

[8] NOVEL NUCLEOSIDE STRATEGIES FOR ANTI-HIV AND ANTI-HSV THERAPY [J].

HERDEWIJN, PAMM .

ANTIVIRAL RESEARCH, 1992, 19 (01) :1-14

[9] Abacavir - A review of its clinical potential in patients with HIV infection [J].

Hervey, PS ;

Perry, CM .

DRUGS, 2000, 60 (02) :447-479

[10] Homo-N-nucleosides: Incorporation into oligonucleotides and antiviral activity. [J].

Hossain, N ;

Hendrix, C ;

Lescrinier, E ;

VanAerschot, A ;

Busson, R ;

DeClercq, E ;

Herdewijn, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (13) :1465-1468