TRANSITION-STATE ANALOG INHIBITORS OF CHORISMATE MUTASE

被引：25

作者：

CLARKE, T ^{[1
]}

STEWART, JD ^{[1
]}

GANEM, B ^{[1
]}

机构：

[1] CORNELL UNIV,DEPT CHEM,BAKER LAB,ITHACA,NY 14853

来源：

TETRAHEDRON | 1990年 / 46卷 / 03期

关键词：

D O I：

10.1016/S0040-4020(01)81357-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of seven bi- and tricyclic chorismate analogues 9-15 and their biological evaluation as mutase inhibitors is described. A tandem Cope rearrangement/Diels-Alder cycloaddition strategy was employed to prepare tricyclo[3.3.1.02,7]non-3-enes functionalized with carboxylic and/or phosphonic acid groups. © 1990.

引用

收藏

页码：731 / 748

页数：18

相关论文

共 28 条

[1] TRANSITION-STATE STABILIZATION AND ENZYMIC CATALYSIS - KINETIC AND MOLECULAR-ORBITAL STUDIES OF REARRANGEMENT OF CHORISMATE TO PREPHENATE [J].

ANDREWS, PR ;

SMITH, GD ;

YOUNG, IG .

BIOCHEMISTRY, 1973, 12 (18) :3492-3498

[2] REARRANGEMENT OF CHORISMATE TO PREPHENATE - USE OF CHORISMATE MUTASE INHIBITORS TO DEFINE TRANSITION-STATE STRUCTURE [J].

ANDREWS, PR ;

CAIN, EN ;

RIZZARDO, E ;

SMITH, GD .

BIOCHEMISTRY, 1977, 16 (22) :4848-4852

[3] A DIRECT SYNTHESIS OF 1-CYCLOALKENYLPHOSPHONATES [J].

BANERJEE, S ;

ENGEL, R ;

AXELRAD, G .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1983, 15 (01) :15-18

[4] CHORISMATE MUTASE INHIBITORS - SYNTHESIS AND EVALUATION OF SOME POTENTIAL TRANSITION-STATE ANALOGS [J].

BARTLETT, PA ;

NAKAGAWA, Y ;

JOHNSON, CR ;

REICH, SH ;

LUIS, A .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3195-3210

[5] AN INHIBITOR OF CHORISMATE MUTASE RESEMBLING THE TRANSITION-STATE CONFORMATION [J].

BARTLETT, PA ;

JOHNSON, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7792-7793

[6]

BERCHTOLD G, 1986, COMMUNICATION

[7] INHIBITION OF CHORISMATE MUTASE ACTIVITY OF CHORISMATE MUTASE-PREPHENATE DEHYDROGENASE FROM AEROBACTER-AEROGENES [J].

CHAO, HSI ;

BERCHTOLD, GA .

BIOCHEMISTRY, 1982, 21 (11) :2778-2781

[8] STEREOSELECTIVE FRAGMENTATION OF A TRICYCLIC DIESTER LEADING TO A POTENT CHORISMATE MUTASE TRANSITION-STATE INHIBITOR [J].

CLARKE, T ;

STEWART, JD ;

GANEM, B .

TETRAHEDRON LETTERS, 1987, 28 (50) :6253-6256

[9] ALPHA-METHYLENE-GAMMA-PHOSTONES (5,5-DI- AND 5-MONOALKYL-2-METHOXY-3-METHYLENE-1,2-OXAPHOSPHOLAN-2-ONES) - A PHOSPHORUS ANALOG OF THE ONE-STEP REFORMATSKY SYNTHESIS OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES FROM KETONES AND ALDEHYDES [J].

COLLARD, JN ;

BENEZRA, C .

TETRAHEDRON LETTERS, 1982, 23 (36) :3725-3728

[10] SOME REARRANGEMENTS OF UNSATURATED PHOSPHONATE ESTERS [J].

COOPER, D ;

TRIPPETT, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (07) :2127-2133