Modified dideoxynucleosides: Synthesis of 2'-N-alkyl-3'-hydroxyalkyl-1',2'-isoxazolidinyl thymidine and 5-fluorouridine derivatives

被引：37

作者：

Chiacchio, U

Gumina, G

Rescifina, A

Romeo, R

Uccella, N

Casuscelli, F

Piperno, A

Romeo, G

机构：

[1] UNIV ARCAVACATA,DIPARTIMENTO CHIM,I-87036 ARCAVACATA,ITALY

[2] UNIV MESSINA,DIPARTIMENTO FARMACO CHIM,I-98168 MESSINA,ITALY

来源：

TETRAHEDRON | 1996年 / 52卷 / 26期

关键词：

D O I：

10.1016/0040-4020(96)00437-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isoxazolidine nucleosides bearing an hydroxyl group at C-3, have been prepared in only three steps, with overall high yields. The synthetic approach is based on the 1,3-dipolar cycloaddition of 3-carboxyalkyl- or acylnitrones to vinyl acetate, followed by condensation with silylated thymine or 5-fluorouracil and NaBH4 reduction. (C) 1996 Elsevier Science Ltd

引用

收藏

页码：8889 / 8898

页数：10

相关论文

共 33 条

[11] INHIBITION OF THE REPLICATION OF HEPATITIS-B VIRUS INVITRO BY 2',3'-DIDEOXY-3'-THIACYTIDINE AND RELATED ANALOGS [J].

DOONG, SL ;

TSAI, CH ;

SCHINAZI, RF ;

LIOTTA, DC ;

CHENG, YC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (19) :8495-8499

[12]

FRICK LW, 1993, J ANTIMICROB AGENTS, V37, P2275

[13] THE ANTI-HEPATITIS-B VIRUS ACTIVITIES, CYTOTOXICITIES, AND ANABOLIC PROFILES OF THE (-) AND (+) ENANTIOMERS OF CIS-5-FLUORO-1-[2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]CYTOSINE [J].

FURMAN, PA ;

DAVIS, M ;

LIOTTA, DC ;

PAFF, M ;

FRICK, LW ;

NELSON, DJ ;

DORNSIFE, RE ;

WURSTER, JA ;

WILSON, LJ ;

FYFE, JA ;

TUTTLE, JV ;

MILLER, WH ;

CONDREAY, L ;

AVERETT, DR ;

SCHINAZI, RF ;

PAINTER, GR .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (12) :2686-2692

[14] THE CONFIGURATIONS OF N-METHYL-BUTYL-ALPHA-METHOXYCARBONYLMETHANIMINE AND N-TERT-BUTYL-ALPHA-METHOXYCARBONYLMETHANIMINE N-OXIDES [J].

INOUYE, Y ;

TAKAYA, K ;

KAKISAWA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (11) :3541-3542

[15] CURRENT PROGRESS ON NUCLEOSIDE ANTIBIOTICS [J].

ISONO, K .

PHARMACOLOGY & THERAPEUTICS, 1991, 52 (03) :269-286

[16] STRUCTURE-ACTIVITY-RELATIONSHIPS AND CONFORMATIONAL FEATURES OF ANTIHERPETIC PYRIMIDINE AND PURINE NUCLEOSIDE ANALOGS - A REVIEW [J].

KULIKOWSKI, T .

PHARMACY WORLD & SCIENCE, 1994, 16 (02) :127-138

[17] SYNTHESIS OF (+/-)-ALLOSEDAMINE BY IODIDE TREATMENT OF ISOXAZOLIDINIUM SALTS [J].

LIGUORI, A ;

OTTANA, R ;

ROMEO, G ;

SINDONA, G ;

UCCELLA, N .

CHEMISCHE BERICHTE, 1989, 122 (10) :2019-2020

[18] N,O-HETEROCYCLES .24. NOVEL-APPROACH TO THE RING-OPENING REACTION OF ISOXAZOLIDINIUM SALTS TO 1,3-AMINO ALCOHOLS [J].

LIGUORI, A ;

ROMEO, G ;

SINDONA, G ;

UCCELLA, N .

CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (01) :105-109

[19]

LIGUORI A, 1978, MAGNETIC RESON CHEM, V26, P974

[20]

LIGUORI A, 1989, CHEM BER, V122, P2020

← 1 2 3 4 →