Novel TSAO derivatives, synthesis and anti-HIV-1 activity of allofuranosyl-TSAO-T analogues

被引：2

作者：

Alvarez, R

SanFelix, A

DeClercq, E

Balzarini, J

Camarasa, MJ

机构：

[1] CSIC,INST QUIM MED,E-28006 MADRID,SPAIN

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

来源：

NUCLEOSIDES & NUCLEOTIDES | 1996年 / 15卷 / 1-3期

关键词：

D O I：

10.1080/07328319608002389

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Novel TSAO-T analogues, in which the ribofuranosyl moiety has been replaced by an hexofuranosyl sugar moiety, have been prepared and evaluated for their inhibitory effect on HIV-1 replication in cell culture. In contrast to the prototype compound TSAO-T, the hexofuranosyl derivatives proved not active at subtoxic concentrations.

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收藏

页码：349 / 359

页数：11

相关论文

共 21 条

[1] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].

ALVAREZ, R ;

VELAZQUEZ, S ;

SANFELIX, A ;

AQUARO, S ;

DECLERCQ, E ;

PERNO, CF ;

KARLSSON, A ;

BALZARINI, J ;

CAMARASA, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194

[2] METABOLISM AND PHARMACOKINETICS OF THE ANTI-HIV-1-SPECIFIC INHIBITOR [1-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3-N-METHYL-THYMINE]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOLE-2'',2''-DIOXIDE) [J].

BALZARINI, J ;

NAESENS, L ;

BOHMAN, C ;

PEREZPEREZ, MJ ;

SANFELIX, A ;

CAMARASA, MJ ;

DECLERCQ, E .

BIOCHEMICAL PHARMACOLOGY, 1993, 46 (01) :69-77

[3] [2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOLE-2'',2''-DIOXIDE) (TSAO) DERIVATIVES OF PURINE AND PYRIMIDINE NUCLEOSIDES AS POTENT AND SELECTIVE INHIBITORS OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 [J].

BALZARINI, J ;

PEREZPEREZ, MJ ;

SANFELIX, A ;

VELAZQUEZ, S ;

CAMARASA, MJ ;

DECLERCQ, E .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (05) :1073-1080

[4] 2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-3'-SPIRO-5''-(4''-AMINO-1',2''-OXATHIOLE-2'',2''-DIOXIDE)PYRIMIDINE (TSAO) NUCLEOSIDE ANALOGS - HIGHLY SELECTIVE INHIBITORS OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 THAT ARE TARGETED AT THE VIRAL REVERSE-TRANSCRIPTASE [J].

BALZARINI, J ;

PEREZPEREZ, MJ ;

SANFELIX, A ;

SCHOLS, D ;

PERNO, CF ;

VANDAMME, AM ;

CAMARASA, MJ ;

DECLERCQ, E .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (10) :4392-4396

[5]

BALZARINI J, 1992, J BIOL CHEM, V267, P11831

[6] HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 (HIV-1) STRAINS SELECTED FOR RESISTANCE AGAINST THE HIV-1-SPECIFIC [2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOLE-2'',2''-DIOXIDE)]-BETA-D-PENTOFURANOSYL (TSAO) NUCLEOSIDE ANALOGS RETAIN SENSITIVITY TO HIV-1-SPECIFIC NONNUCLEOSIDE INHIBITORS [J].

BALZARINI, J ;

KARLSSON, A ;

VANDAMME, AM ;

PEREZPEREZ, MJ ;

ZHANG, H ;

VRANG, L ;

OBERG, B ;

BACKBRO, K ;

UNGE, T ;

SANFELIX, A ;

VELAZQUEZ, S ;

CAMARASA, MJ ;

DECLERCQ, E .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (15) :6952-6956

[7] SENSITIVITY OF (138 GLU-]LYS) MUTATED HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 (HIV-1) REVERSE-TRANSCRIPTASE (RT) TO HIV-1-SPECIFIC RT-INHIBITORS [J].

BALZARINI, J ;

KLEIM, JP ;

RIESS, G ;

CAMARASA, MJ ;

DECLERCQ, E ;

KARLSSON, A .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1994, 201 (03) :1305-1312

[8] HIV-1-SPECIFIC REVERSE-TRANSCRIPTASE INHIBITORS SHOW DIFFERENTIAL ACTIVITY AGAINST HIV-1 MUTANT STRAINS CONTAINING DIFFERENT AMINO-ACID SUBSTITUTIONS IN THE REVERSE-TRANSCRIPTASE [J].

BALZARINI, J ;

KARLSSON, A ;

PEREZPEREZ, MJ ;

VRANG, L ;

WALBERS, J ;

ZHANG, H ;

OBERG, B ;

VANDAMME, AM ;

CAMARASA, MJ ;

DECLERCQ, E .

VIROLOGY, 1993, 192 (01) :246-253

[9]

Balzarini Jan, 1993, Drugs of the Future, V18, P1043

[10] SYNTHESIS OF BRANCHED AMINATED SUGARS .2. SYNTHESIS AND REACTIONS OF SPIRO-AZIRIDINES - PRELIMINARY COMMUNICATION [J].

BOURGEOIS, JM .

HELVETICA CHIMICA ACTA, 1974, 57 (08) :2553-2557