SYNTHESIS OF THE 2,3-EPOXY-2,3-DIHYDRO-2,3-DIMETHYLBENZO[B]FURAN, THE PROPOSED ULTIMATE MUTAGEN OF THE BENZOFURAN DIOXETANES

被引：25

作者：

ADAM, W ^{[1
]}

HADJIARAPOGLOU, L ^{[1
]}

MOSANDL, T ^{[1
]}

SAHAMOLLER, CR ^{[1
]}

WILD, D ^{[1
]}

机构：

[1] UNIV WURZBURG,INST PHARMACOL & TOXIKOL,W-8700 WURZBURG,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 02期

关键词：

D O I：

10.1002/anie.199102001

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dioxetanes can be precursors for mutagenic epoxides-this provocative hypothesis is the result of this study. Epoxidation of the benzofurans 1 with dimethyldioxirane and deoxygenation of the benzofuran dioxetanes 3 with dimethyl sulfides allows for the first time the synthesis of libile furanepoxides 2. Compounds 2 and 3 are strongly mutagenic in the histidine-auxotrophic Salmonella typhimurium strain TA 100. X = H, Ac.

引用

页码：200 / 202

页数：3

共 21 条

[1] PHOTOBIOLOGICAL STUDIES WITH DIOXETANES IN ISOLATED DNA, BACTERIA, AND MAMMALIAN-CELLS
ADAM, W
BEINHAUER, A
MOSANDL, T
SAHAMOLLER, C
VARGAS, F
EPE, B
MULLER, E
SCHIFFMANN, D
WILD, D
[J]. ENVIRONMENTAL HEALTH PERSPECTIVES, 1990, 88 : 89 - 97
[2] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS
ADAM, W
CURCI, R
EDWARDS, JO
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) : 205 - 211
[3] Adam W., 1986, PRIMARY CHANGES CONT, P64
[4] PREPARATION OF THE 8,9-EPOXIDE OF THE MYCOTOXIN AFLATOXIN-B1 - THE ULTIMATE CARCINOGENIC SPECIES
BAERTSCHI, SW
RANEY, KD
STONE, MP
HARRIS, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) : 7929 - 7931
[5] BERDAHL DR, 1983, ISR J CHEM, V23, P409
[6] PHOTOCHEMISTRY AND PHOTOBIOLOGY WITHOUT LIGHT
CILENTO, G
ADAM, W
[J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1988, 48 (03) : 361 - 368
[7] CURCI R, 1990, ADV OXYGENATED PROCE, V2, pCH1
[8] JENNINGS BW, 1976, J ORG CHEM, V41, P407
[9] PRODUCTION OF PYRIMIDINE DIMERS IN DNA IN DARK
LAMOLA, AA
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1971, 43 (04) : 893 - &
[10] LOWN JW, 1986, PHOTOBIOCH PHOTOBIOP, V12, P295

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