Cyclic saligenyl phosphotriesters of 2',3'-dideoxy-2',3'-didehydrothymidine (d4T) - A new pro-nucleotide approach

被引:48
作者
Meier, C [1 ]
Lorey, M [1 ]
DeClercq, E [1 ]
Balzarini, J [1 ]
机构
[1] CATHOLIC UNIV LEUVEN,REGA INST MED RES,B-3000 LOUVAIN,BELGIUM
关键词
D O I
10.1016/S0960-894X(96)00597-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis of a new pro-nucleotide approach for d4TMP 2 based on cycloSal-d4TMP 3a-d is described. Phosphotriesters 3 release d4TMP 2 selectively by a controlled, chemically induced tandem reaction. CycloSal-phosphotriesters 3 exhibited high biological activity against HIV-1/HIV-2 in CEM cells which was retained in CEM TK- cells. (C) 1997, Published by Elsevier Science Ltd.
引用
收藏
页码:99 / 104
页数:6
相关论文
共 22 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]  
BALZARINI J, 1989, J BIOL CHEM, V264, P6127
[3]  
BALZARINI J, 1987, MOL PHARMACOL, V32, P162
[4]   SYNTHESIS AND BIOLOGICAL PROPERTIES OF NOVEL PHOSPHOTRIESTERS - A NEW APPROACH TO THE INTRODUCTION OF BIOLOGICALLY-ACTIVE NUCLEOTIDES INTO CELLS [J].
FARROW, SN ;
JONES, AS ;
KUMAR, A ;
WALKER, RT ;
BALZARINI, J ;
DECLERCQ, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1400-1406
[5]   Increase of the anti-HIV activity of D4T in human T-cell culture by the use of the sate pronucleotide approach [J].
Girardet, JL ;
Perigaud, C ;
Aubertin, AM ;
Gosselin, G ;
Kirn, A ;
Imbach, JL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (24) :2981-2984
[6]  
HABEL L, 1994, THESIS U FRANKFURT
[7]   NUCLEOSIDES .9. FORMATION OF 2',3'-UNSATURATED PHYRIMIDINE NUCLEOSIDES VIA A NOVEL BETA-ELIMINATION REACTION [J].
HORWITZ, JP ;
CHUA, J ;
DAROOGE, MA ;
NOEL, M ;
KLUNDT, IL .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (01) :205-&
[8]   MINIREVIEW - NUCLEOTIDE PRODRUGS [J].
JONES, RJ ;
BISCHOFBERGER, N .
ANTIVIRAL RESEARCH, 1995, 27 (1-2) :1-17
[9]   1-(2,3-DIDEOXY-BETA-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE - A HIGHLY POTENT AND SELECTIVE ANTI-HIV AGENT [J].
MANSURI, MM ;
STARRETT, JE ;
GHAZZOULI, I ;
HITCHCOCK, MJM ;
STERZYCKI, RZ ;
BRANKOVAN, V ;
LIN, TS ;
AUGUST, EM ;
PRUSOFF, WH ;
SOMMADOSSI, JP ;
MARTIN, JC .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (02) :461-466
[10]   COMPARISON OF INVITRO BIOLOGICAL PROPERTIES AND MOUSE TOXICITIES OF 3 THYMIDINE ANALOGS ACTIVE AGAINST HUMAN-IMMUNODEFICIENCY-VIRUS [J].
MANSURI, MM ;
HITCHCOCK, MJM ;
BUROKER, RA ;
BREGMAN, CL ;
GHAZZOULI, I ;
DESIDERIO, JV ;
STARRETT, JE ;
STERZYCKI, RZ ;
MARTIN, JC .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1990, 34 (04) :637-641