6-Guanidinopurine nucleosides and their analogues

被引：16

作者：

Cesnek, M ^{[1
]}

Holy, A ^{[1
]}

Masojídková, M ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic

来源：

TETRAHEDRON | 2002年 / 58卷 / 15期

关键词：

6-guanidinopurines; purine ribonucleosides; purine 2 '-deoxyribonucleosides; acyclic nucleoside phosphonates; acyclic nucleosides; guanidine derivatives;

D O I：

10.1016/S0040-4020(02)00186-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general synthetic approach to 6-guanidinopurines, their ribonucleosides, 2-deoxyribonucleosides, acyclic nucleoside analogues and acyclic nucleoside phosphonates was developed. The approach consists in the reaction of the 6-chloropurine derivatives with guanidine solution in DMF under DABCO catalysis. This method was used to synthesize 6-guanidinopurine and 2-amino-6-guanidinopurine derivatives. Acyclic nucleosides and acyclic nucleoside phosphonates were also obtained by alkylation of the 6-guanidinopurine bases. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2985 / 2996

页数：12

共 42 条

[1] KINETICS OF REACTIONS IN HETEROCYCLES .11. REACTIONS OF 2-CHLORO-7-METHYLPURINES, 6-CHLORO-7-METHYLPURINES, AND 8-CHLORO-7-METHYLPURINES AND 2-METHYLSULPHONYL-7(9)-METHYLPURINES, 6-METHYLSULPHONYL-7(9)-METHYLPURINES, AND 8-METHYLSULPHONYL-7(9)-METHYLPURINES WITH HYDROXIDE IONS [J].

BADGER, RJ ;

BARLIN, GB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (15) :1854-1859

[2] 1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE - AN ATTRACTIVE REAGENT FOR GUANYLATION OF AMINES AND ITS APPLICATION TO PEPTIDE-SYNTHESIS [J].

BERNATOWICZ, MS ;

WU, YL ;

MATSUEDA, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2497-2502

[3] PURINE STUDIES .6. FORMATION, HYDROLYSIS, AND AMINOLYSIS OF SOME PURINE SULPHOXIDES AND SULPHONES [J].

BROWN, DJ ;

FORD, PW .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18) :2620-&

[4] AROMATICITY IN HETEROCYCLIC SYSTEMS .V. BROMINATION STUDIES OF CERTAIN PURINES PYRROLO[3,2-D] PYRIMIDINES AND PYRAZOLO[4,3-D]PYRIMIDINES [J].

CASSIDY, F ;

OLSEN, RK ;

ROBINS, RK .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (04) :461-&

[5] ADENOSINE RECEPTORS - TARGETS FOR FUTURE DRUGS [J].

DALY, JW .

JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (03) :197-207

[6] (S)-9-(2,3-DIHYDROXYPROPYL)ADENINE - ALIPHATIC NUCLEOSIDE ANALOG WITH BROAD-SPECTRUM ANTI-VIRAL ACTIVITY [J].

DECLERCQ, E ;

DESCAMPS, J ;

DESOMER, P .

SCIENCE, 1978, 200 (4341) :563-565

[7] INHIBITORY EFFECT OF A BROAD-SPECTRUM ANTI-VIRAL AGENT, "(S)-9-(2,3-DIHYDROXYPROPYL)ADENINE, ON SPERMATOGENESIS IN MICE [J].

DECLERCQ, E ;

LEYTEN, R ;

SOBIS, H ;

MATOUSEK, J ;

HOLY, A ;

DESOMER, P .

TOXICOLOGY AND APPLIED PHARMACOLOGY, 1981, 59 (03) :441-451

[8] ANTI-VIRAL ACTIVITY OF ALIPHATIC NUCLEOSIDE ANALOGS - STRUCTURE-FUNCTION RELATIONSHIP [J].

DECLERCQ, E ;

HOLY, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (05) :510-513

[9] Synthesis of 4-guanidinopyrimidine nucleosides for triple helix-mediated guanine and cytosine recognition. [J].

Doronina, SO ;

Behr, JP .

TETRAHEDRON LETTERS, 1998, 39 (07) :547-550

[10] Guanidino-containing drugs in cancer chemotherapy: biochemical and clinical pharmacology [J].

Ekelund, S ;

Nygren, P ;

Larsson, R .

BIOCHEMICAL PHARMACOLOGY, 2001, 61 (10) :1183-1193

← 1 2 3 4 5 →