LIPOPHILIC 5',5'-O-DINUCLEOSIDE-ALPHA -HYDROXYBENZYLPHOSPHONIC ACID-ESTERS AS POTENTIAL PRODRUGS OF 2',3'-DIDEOXYTHYMIDINE (DDT)

被引：39

作者：

MEIER, C

机构：

[1] Institut Für Organische Chemie, Universität Frankfurt, D-60439

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 1993年 / 32卷 / 12期

关键词：

D O I：

10.1002/anie.199317041

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Phosphonylated and phosphonylated derivatives of the antiviral active nucleoside analogue 2′,3′‐dideoxythymidine (ddT) can be released from the dinucleoside‐α‐hydroxybenzylphosphonic acid esters (1). Depending on the substituents at the aryl group, phosphonate–phosphate rearrangement or direct cleavage was observed. Consequently, compounds of type 1 can, in principle, serve as prodrugs of phosphorylated or phosphonylated nucleosides. Araryl. (Figure Presented.) Copyright © 1993 by VCH Verlagsgesellschaft mbH, Germany

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页码：1704 / 1706

页数：3

相关论文

共 24 条

[1] ESTIMATION OF THE LIPOPHILICITY OF ANTI-HIV NUCLEOSIDE ANALOGS BY DETERMINATION OF THE PARTITION-COEFFICIENT AND RETENTION TIME ON A LICHROSPHER-60 RP-8 HPLC COLUMN [J].

BALZARINI, J ;

COOLS, M ;

DECLERCQ, E .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1989, 158 (02) :413-422

[2] INSECTICIDAL PHOSPHATES OBTAINED BY A NEW REARRANGEMENT REACTION [J].

BARTHEL, WF ;

ALEXANDER, BH ;

GIANG, PA ;

HALL, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (09) :2424-2427

[3] ORGANOPHOSPHORUS CHEMISTRY .17. KINETICS AND MECHANISM OF PERKOW REACTION [J].

BOROWITZ, IJ ;

BOROWITZ, GB ;

SCHUESSL.D ;

FIRSTENB.S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (05) :1623-&

[4]

ENGELS JW, 1982, J MED CHEM, V20, P907

[5] PHOSPHORYLATION OF 3'-AZIDO-3'-DEOXYTHYMIDINE AND SELECTIVE INTERACTION OF THE 5'-TRIPHOSPHATE WITH HUMAN-IMMUNODEFICIENCY-VIRUS REVERSE-TRANSCRIPTASE [J].

FURMAN, PA ;

FYFE, JA ;

STCLAIR, MH ;

WEINHOLD, K ;

RIDEOUT, JL ;

FREEMAN, GA ;

LEHRMAN, SN ;

BOLOGNESI, DP ;

BRODER, S ;

MITSUYA, H ;

BARRY, DW .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1986, 83 (21) :8333-8337

[6]

GAREGG PJ, 1985, CHEM SCRIPTA, V25, P280

[7] NUCLEOSIDE H-PHOSPHONATES .3. CHEMICAL SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES BY THE HYDROGENPHOSPHONATE APPROACH [J].

GAREGG, PJ ;

LINDH, I ;

REGBERG, T ;

STAWINSKI, J ;

STROMBERG, R ;

HENRICHSON, C .

TETRAHEDRON LETTERS, 1986, 27 (34) :4051-4054

[8]

GAREGG PJ, 1986, CHEM SCRIPTA, V26, P59

[9]

HAHN EF, 1989, ACS SYM SER, V401, P156

[10] NOVEL SYNTHETIC ASPECTS OF THE PHOSPHONATE-PHOSPHATE REARRANGEMENT .1. AN USEFUL APPROACH TO 1,2-PROPADIENYL PHOSPHATES [J].

HAMMERSCHMIDT, F ;

SCHNEYDER, E ;

ZBIRAL, E .

CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (12) :3891-3897