Guanine, pyrazolo[3,4-d] pyrimidine, and triazolo[4,5-d] pyrimidine (8-azaguanine) phosphonate acyclic derivatives as inhibitors of purine nucleoside phosphorylase

被引:30
作者
Beauchamp, LM [1 ]
Tuttle, JV [1 ]
Rodriguez, ME [1 ]
Sznaidman, ML [1 ]
机构
[1] BURROUGHS WELLCOME CO,DIV EXPTL THERAPY,RES TRIANGLE PK,NC 27709
关键词
D O I
10.1021/jm950736k
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Phosphonate acyclic derivatives of guanines, pyrazolo[3,4-d]pyrimidines, and triazolo[4,5-d]-pyrimidines (8-azaguanines) are inhibitors of the enzyme purine nucleoside phosphorylase (PNPase) with K-i' values ranging from 0.05 to 1.6 mu M. These compounds are enzymatically stable congeners of the potent PNPase inhibitor acyclovir diphosphate (53).
引用
收藏
页码:949 / 956
页数:8
相关论文
共 21 条
[1]   MODIFICATIONS ON THE HETEROCYCLIC BASE OF ACYCLOVIR - SYNTHESES AND ANTIVIRAL PROPERTIES [J].
BEAUCHAMP, LM ;
DOLMATCH, BL ;
SCHAEFFER, HJ ;
COLLINS, P ;
BAUER, DJ ;
KELLER, PM ;
FYFE, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (08) :982-987
[2]   ACYCLONUCLEOSIDE ANALOG INHIBITORS OF MAMMALIAN PURINE NUCLEOSIDE PHOSPHORYLASE [J].
BZOWSKA, A ;
KULIKOWSKA, E ;
SHUGAR, D ;
CHEN, BY ;
LINDBORG, B ;
JOHANSSON, NG .
BIOCHEMICAL PHARMACOLOGY, 1991, 41 (12) :1791-1803
[3]  
Gilbertsen R.B., 1990, COMPREHENSIVE MED CH, V2, P443
[4]  
GILBERTSEN RB, 1990, J BIOL CHEM, V265, P1812
[5]   9-(DIFLUOROPHOSPHONOALKYL)GUANINES AS A NEW CLASS OF MULTISUBSTRATE ANALOG INHIBITORS OF PURINE NUCLEOSIDE PHOSPHORYLASE [J].
HALAZY, S ;
EHRHARD, A ;
DANZIN, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :315-317
[6]   PHOSPHONATE DERIVATIVES OF N9-BENZYLGUANINE - A NEW CLASS OF POTENT PURINE NUCLEOSIDE PHOSPHORYLASE INHIBITORS [J].
HALAZY, S ;
EGGENSPILLER, A ;
EHRHARD, A ;
DANZIN, C .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (05) :407-410
[7]   AN IMPROVED FUSION METHOD FOR THE SYNTHESIS OF PURINE NUCLEOSIDES - THE ACID-CATALYZED REACTIONS OF N(7)-ACYLPURINES OR N(9)-ACYLPURINES WITH ACYLATED SUGARS [J].
ISHIDO, Y ;
HOSONO, A ;
ISOME, S ;
MARUYAMA, A ;
SATO, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1964, 37 (09) :1389-1390
[8]   9-[(PHOSPHONOALKYL)BENZYL]GUANINES - MULTISUBSTRATE ANALOG INHIBITORS OF HUMAN ERYTHROCYTE PURINE NUCLEOSIDE PHOSPHORYLASE [J].
KELLEY, JL ;
LINN, JA ;
MCLEAN, EW ;
TUTTLE, JV .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (22) :3455-3463
[9]   [[(GUANINYLALKYL)PHOSPHINICO]METHYL]PHOSPHONIC ACIDS - MULTISUBSTRATE ANALOG INHIBITORS OF HUMAN ERYTHROCYTE PURINE NUCLEOSIDE PHOSPHORYLASE [J].
KELLEY, JL ;
MCLEAN, EW ;
CROUCH, RC ;
AVERETT, DR ;
TUTTLE, JV .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (06) :1005-1014
[10]   REGIOSELECTIVE ALKYLATION OF 6-(BETA-METHOXYETHOXY)GUANINE TO GIVE 9-ALKYLGUANINE DERIVATIVE [J].
KJELLBERG, J ;
LILJENBERG, M ;
JOHANSSON, NG .
TETRAHEDRON LETTERS, 1986, 27 (07) :877-880