Synthesis and antiproliferative activity of 2'-O-allyl-1-beta-D-arabinofuranosyl-uracil, -cytosine and -adenine

被引：10

作者：

Manfredini, S

Baraldi, PG

Bazzanini, R

Simoni, D

Balzarini, J

DeClercq, E

机构：

[1] UNIV PALERMO,IST FARMACOCHIM,PALERMO,ITALY

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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1997年 / 7卷 / 04期

关键词：

D O I：

10.1016/S0960-894X(97)00044-9

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

With the aim to design potential inhibitors of ribonucleotide reductase (RR), 2'-O-allyl-beta-D-arabinofuranosyl-uracil (4), -cytosine (7) and -adenosine (10) were prepared and evaluated for their cytostatic activity against Molt4/C8, CEM and L1210 cell lines. Although our preliminary data do not allow to assess if RR is the intracellular target, the results point to differences in the (anti)metabolic behavior of these compounds. This study also offers a general synthesis of 2'-O-allyl-beta-D-arabinofuranosyl nucleosides for potential applications in the preparation of 2'-O-allyl-beta-D-oligoarabino nucleotides. (C) 1997, Elsevier Science Ltd.

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页码：473 / 478

页数：6

相关论文

共 21 条

[1] MECHANISM OF INACTIVATION OF ESCHERICHIA-COLI RIBONUCLEOTIDE REDUCTASE BY 2'-CHLORO-2'-DEOXYURIDINE 5'-DIPHOSPHATE - EVIDENCE FOR GENERATION OF A 2'-DEOXY-3'-KETONUCLEOTIDE VIA A NET 1,2 HYDROGEN SHIFT [J].

ATOR, MA ;

STUBBE, J .

BIOCHEMISTRY, 1985, 24 (25) :7214-7221

[2] 2'-DEOXY-2'-METHYLENECYTIDINE AND 2'-DEOXY-2',2'-DIFLUOROCYTIDINE 5'-DIPHOSPHATES - POTENT MECHANISM-BASED INHIBITORS OF RIBONUCLEOTIDE REDUCTASE [J].

BAKER, CH ;

BANZON, J ;

BOLLINGER, JM ;

STUBBE, J ;

SAMANO, V ;

ROBINS, MJ ;

LIPPERT, B ;

JARVI, E ;

RESVICK, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) :1879-1884

[3] Formation of a free radical of the sulfenylimine type in the mouse ribonucleotide reductase reaction with 2'-azido-2'-deoxycytidine 5'-diphosphate [J].

Behravan, G ;

Sen, S ;

Rova, U ;

Thelander, L ;

Eckstein, F ;

Graslund, A .

BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 1995, 1264 (03) :323-329

[4]

CHU Y, 1969, BIOCHEM PHARMACOL, V17, P753

[5] 4-(1,2,4-TRIAZOL-1-YL) AND 4-(3-NITRO-1,2,4-TRIAZOL-1-YL)-1-(BETA-D-2,3,5-TRI-O-ACETYLARABINOFURANOSYL)PYRIMIDIN-2(1H)-ONES - VALUABLE INTERMEDIATES IN THE SYNTHESIS OF DERIVATIVES OF "1-(BETA-D-ARABINOFURANOSYL)CYTOSINE (ARA-C) [J].

DIVAKAR, KJ ;

REESE, CB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (05) :1171-1176

[6]

EHRENBERG A, 1972, J BIOL CHEM, V247, P3485

[7] ENHANCEMENT BY HYDROXYUREA OF THE ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 POTENCY OF 2'-BETA-FLUORO-2',3'-DIDEOXYADENOSINE IN PERIPHERAL-BLOOD MONONUCLEAR CELLS [J].

GAO, WY ;

MITSUYA, H ;

DRISCOLL, JS ;

JOHNS, DG .

BIOCHEMICAL PHARMACOLOGY, 1995, 50 (02) :274-276

[8] REGIOSELECTIVE 2'/3'-O-ALLYLATION OF PYRIMIDINE RIBONUCLEOSIDES USING PHASE-TRANSFER CATALYSIS [J].

GOPALAKRISHNAN, V ;

KUMAR, V ;

GANESH, KN .

NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (06) :1263-1273

[9] SYNTHESIS OF 2-DEOXY-2,2-DIFLUORO-D-RIBOSE AND 2-DEOXY-2,2-DIFLUORO-D-RIBOFURANOSYL NUCLEOSIDES [J].

HERTEL, LW ;

KROIN, JS ;

MISNER, JW ;

TUSTIN, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2406-2409

[10] 5'-O-ALKYL AND ACYL PRODRUGS OF 1-BETA-D-ARABINOFURANOSYL-E-5-(2-BROMOVINYL)URACIL [J].

KANO, F ;

IJICHI, K ;

ASHIDA, N ;

WATANABE, Y ;

SAKATA, S ;

MACHIDA, H .

ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 1994, 5 (02) :74-82