SYNTHESIS OF AND ANALYSIS OF THIOL ADDITIONS TO BETA-ALKYL-ALPHA,BETA-UNSATURATED TRIFLUOROMETHYL KETONES

被引：31

作者：

LINDERMAN, RJ

JAMOIS, EA

TENNYSON, SD

机构：

[1] Department of Chemistry, North Carolina State University, Raleigh

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 05期

关键词：

D O I：

10.1021/jo00084a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of beta-alkyl-alpha,beta-unsaturated trifluoromethyl ketones have been prepared from the corresponding alpha-acetylenic trifluoromethyl ketones. The addition of sulfur nucleophiles was shown by chemical and F-19 NMR studies to proceed exclusively by 1,4-addition with no indication of any 1,2-addition products. The unsaturated trifluoromethyl ketones have been shown to be effective inhibitors of rat cytosolic glutathione-S-transferase.

引用

收藏

页码：957 / 962

页数：6

相关论文

共 41 条

[1] ENZYME-INHIBITORS - GROUND-STATE TRANSITION-STATE ANALOGS [J].

ABELES, RH .

DRUG DEVELOPMENT RESEARCH, 1987, 10 (04) :221-234

[2] PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES [J].

BEGUE, JP ;

BONNETDELPON, D .

TETRAHEDRON, 1991, 47 (20-21) :3207-3258

[3]

BRANDSMA L, 1971, PREPARATIVE ACETYLEN, P71

[4] THE ROLE OF GLUTATHIONE AND GLUTATHIONE TRANSFERASES IN CHEMICAL CARCINOGENESIS [J].

COLES, B ;

KETTERER, B .

CRITICAL REVIEWS IN BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1990, 25 (01) :47-70

[5] STRUCTURE-ACTIVITY-RELATIONSHIPS OF 4-HYDROXYALKENALS IN THE CONJUGATION CATALYZED BY MAMMALIAN GLUTATHIONE TRANSFERASES [J].

DANIELSON, UH ;

ESTERBAUER, H ;

MANNERVIK, B .

BIOCHEMICAL JOURNAL, 1987, 247 (03) :707-713

[6] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[7] CARBONYL ADDITION-REACTIONS - FACTORS AFFECTING HYDRATE-HEMIACETAL AND HEMIACETAL-ACETAL EQUILIBRIUM-CONSTANTS [J].

GUTHRIE, JP .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (06) :898-906

[8] PREPARATION OF 20,20,20-TRIFLUORORETINAL (13-TRIFLUOROMETHYLRETINAL) [J].

HANZAWA, Y ;

KAWAGOE, K ;

KOBAYASHI, N ;

OSHIMA, T ;

KOBAYASHI, Y .

TETRAHEDRON LETTERS, 1985, 26 (24) :2877-2880

[9] PREPARATION OF 19,19,19-TRIFLUORORETINAL (9-TRIFLUOROMETHYLRETINAL) [J].

HANZAWA, Y ;

YAMADA, A ;

KOBAYASHI, Y .

TETRAHEDRON LETTERS, 1985, 26 (24) :2881-2884

[10]

HOFFMANN MG, 1993, TETRAHEDRON, P1057

← 1 2 3 4 5 →