Stereospecific synthesis of two novel cytotoxic pyrazole C-nucleosides from D-glucose

被引：10

作者：

Popsavin, M

Torovic, L

Spaic, S

Stankov, S

Popsavin, V

机构：

[1] Univ Novi Sad, Fac Sci, Inst Chem, YU-21000 Novi Sad, Yugoslavia

[2] Inst Pasteur, YU-21000 Novi Sad, Yugoslavia

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 30期

关键词：

C-nucleosides; isosteres; pyrazoles; cytotoxic activity;

D O I：

10.1016/S0040-4039(00)00894-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A multistep stereospecific synthesis of two novel pyrazole C-nucleosides 12 and 21 has been achieved starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivative 1 as a divergent intermediate. The C-nucleoside 12 was shown to be a moderate inhibitor of the in vitro growth of N2a and BHK 21 tumor cell lines, whereas 21 showed a moderate cytotoxic activity only against N2a cells. (C) 2000 Published by Elsevier Science Ltd.

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收藏

页码：5737 / 5740

页数：4

相关论文

共 7 条

[1] C-GLYCOSYL NUCLEOSIDES .4. SYNTHESES OF SEVERAL 4-(BETA-D-RIBOFURANOSYL)PYRAZOLES [J].

ALBRECHT, HP ;

REPKE, DB ;

MOFFATT, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (15) :2176-2182

[2]

DECLERCQ E, 1990, DESIGN ANTIAIDS DRUG, P1

[3] C-GLYCOSYL NUCLEOSIDES .9. AN APPROACH TO SYNTHESIS OF PURINE-RELATED C-GLYCOSIDES [J].

GUPTA, CM ;

JONES, GH ;

MOFFATT, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (18) :3000-3009

[4] PYRAZOLE-RELATED NUCLEOSIDES - SYNTHESIS AND ANTIVIRAL ANTITUMOR-ACTIVITY OF SOME SUBSTITUTED PYRAZOLE AND PYRAZOLO[4,3-D]-1,2,3-TRIAZIN-4-ONE NUCLEOSIDES [J].

MANFREDINI, S ;

BAZZANINI, R ;

BARALDI, PG ;

GUARNERI, M ;

SIMONI, D ;

MARONGIU, ME ;

PANI, A ;

TRAMONTANO, E ;

LACOLLA, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (05) :917-924

[5] PREPARATION OF 2,5-ANHYDRO-3,4,6-TRI-O-BENZOYL-D-ALLONONITRILE FROM D-GLUCOSE [J].

POPSAVIN, M ;

POPSAVIN, V ;

VUKOJEVIC, N ;

CSANADI, J ;

MILJKOVIC, D .

CARBOHYDRATE RESEARCH, 1994, 260 (01) :145-150

[6] C-NUCLEOSIDE SYNTHESIS .9. SYNTHESIS OF 3-CARBAMOYL-4-[BETA-D-RIBOFURANOSYL)METHYL]PYRAZOLE, A PYRAZOLE HOMO-C-NUCLEOSIDE [J].

SATO, T ;

NOYORI, R .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) :1195-1196

[7] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANALOGS OF 2'-DEOXY-2'-(3-METHOXYBENZAMIDO)ADENOSINE, A SELECTIVE INHIBITOR OF TRYPANOSOMAL GLYCOSOMAL GLYCERALDEHYDE-3-PHOSPHATE DEHYDROGENASE [J].

VANCALENBERGH, S ;

VERLINDE, CLMJ ;

SOENENS, J ;

DEBRUYN, A ;

CALLENS, M ;

BLATON, NM ;

PEETERS, OM ;

ROZENSKI, J ;

HOL, WGJ ;

HERDEWIJN, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (19) :3838-3849