e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis of the isomeric mono-and bisoxiranylpyrenes

RG Harvey, M Konieczny, J Pataki

Index: Harvey, Ronald G.; Konieczny, Maria; Pataki, John Journal of Organic Chemistry, 1983 , vol. 48, # 17 p. 2930 - 2932

Full Text: HTML

Citation Number: 14

Abstract

l-Oxiranylpyrene (la) exhibits potent mutagenic activity in both bacterial2 and mammalian3 cells, efficiently inhibits replication of c $ X 174 viral DNA: and binds covalently to SV 40 DNA, causing unwinding of the supercoiled DNA helixe2p5 l-Oxiranylpyrene is also a close structural analogue of trans-7, 8-dihydroxy-unti-9, 10-epoxy-7, 8, 9, 10-tetrahydrobenzo [a] pyrene (4) implicated as the ultimate carcinogenic metabolite of ben~ o [u] pyrene.~ In ...

1-(2-PYRENYL)ETHANOL Structure

1-(2-PYRENYL)ETHANOL

~80%

2-ethenylpyrene Structure

2-ethenylpyrene

PYRENE, 4,5-DIHYDRO- Structure

PYRENE, 4,5-DIHYDRO-

~%

2-ethenylpyrene Structure

2-ethenylpyrene

4,5,9,10-Tetrahydropyrene Structure

4,5,9,10-Tetrah...

~%

2-ethenylpyrene Structure

2-ethenylpyrene

2-Acetylpyrene Structure

~%

2-ethenylpyrene Structure

2-ethenylpyrene

1-(4,5,9,10-tetrahydropyren-2-yl)ethanone Structure

1-(4,5,9,10-tet...

~%

2-ethenylpyrene Structure

2-ethenylpyrene

2,7-diacetylpyrene Structure

2,7-diacetylpyrene

~97%

1-[7-(1-hydroxyethyl)pyren-2-yl]ethanol Structure

1-[7-(1-hydroxy...

PYRENE, 4,5-DIHYDRO- Structure

PYRENE, 4,5-DIHYDRO-

~%

1-[7-(1-hydroxyethyl)pyren-2-yl]ethanol Structure

1-[7-(1-hydroxy...

4,5,9,10-Tetrahydropyrene Structure

4,5,9,10-Tetrah...

~%

1-[7-(1-hydroxyethyl)pyren-2-yl]ethanol Structure

1-[7-(1-hydroxy...

1-(7-acetyl-4,5,9,10-tetrahydropyren-2-yl)ethanone Structure

1-(7-acetyl-4,5...

~%

1-[7-(1-hydroxyethyl)pyren-2-yl]ethanol Structure

1-[7-(1-hydroxy...

pyrene-4-carbaldehyde Structure

pyrene-4-carbal...

dimethylsulphonium methylide Structure

dimethylsulphon...

~88%

4-Pyrenyloxirane Structure

4-Pyrenyloxirane

4-Bromopyrene Structure

~%

4-Pyrenyloxirane Structure

4-Pyrenyloxirane

1-(6-acetylpyren-1-yl)ethanone Structure

1-(6-acetylpyre...

~41%

2-bromo-1-[6-(2-bromoacetyl)pyren-1-yl]ethanone Structure

2-bromo-1-[6-(2...

1-(8-acetylpyren-1-yl)ethanone Structure

1-(8-acetylpyre...

~77%

2-bromo-1-[8-(2-bromoacetyl)pyren-1-yl]ethanone Structure

2-bromo-1-[8-(2...

PYRENE, 4,5-DIHYDRO- Structure

PYRENE, 4,5-DIHYDRO-

~%

1-(2-PYRENYL)ETHANOL Structure

1-(2-PYRENYL)ETHANOL

2-bromo-1-[6-(2-bromoacetyl)pyren-1-yl]ethanone Structure

2-bromo-1-[6-(2...

~63%

2-[6-(oxiran-2-yl)pyren-1-yl]oxirane Structure

2-[6-(oxiran-2-...

1-(6-acetylpyren-1-yl)ethanone Structure

1-(6-acetylpyre...

~%

2-[6-(oxiran-2-yl)pyren-1-yl]oxirane Structure

2-[6-(oxiran-2-...

2-Acetylpyrene Structure

~%

1-(2-PYRENYL)ETHANOL Structure

1-(2-PYRENYL)ETHANOL

4,5,9,10-Tetrahydropyrene Structure

4,5,9,10-Tetrah...

~%

1-(2-PYRENYL)ETHANOL Structure

1-(2-PYRENYL)ETHANOL

1-(4,5,9,10-tetrahydropyren-2-yl)ethanone Structure

1-(4,5,9,10-tet...

~%

1-(2-PYRENYL)ETHANOL Structure

1-(2-PYRENYL)ETHANOL

2-bromo-1-[8-(2-bromoacetyl)pyren-1-yl]ethanone Structure

2-bromo-1-[8-(2...

~66%

2-[8-(oxiran-2-yl)pyren-1-yl]oxirane Structure

2-[8-(oxiran-2-...

1-(8-acetylpyren-1-yl)ethanone Structure

1-(8-acetylpyre...

~%

2-[8-(oxiran-2-yl)pyren-1-yl]oxirane Structure

2-[8-(oxiran-2-...

2-ethenylpyrene Structure

2-ethenylpyrene

~64%

2-pyren-2-yloxirane Structure

2-pyren-2-yloxirane

PYRENE, 4,5-DIHYDRO- Structure

PYRENE, 4,5-DIHYDRO-

~%

2-pyren-2-yloxirane Structure

2-pyren-2-yloxirane

4,5,9,10-Tetrahydropyrene Structure

4,5,9,10-Tetrah...

~%

2-pyren-2-yloxirane Structure

2-pyren-2-yloxirane

2-Acetylpyrene Structure

~%

2-pyren-2-yloxirane Structure

2-pyren-2-yloxirane

1-(4,5,9,10-tetrahydropyren-2-yl)ethanone Structure

1-(4,5,9,10-tet...

~%

2-pyren-2-yloxirane Structure

2-pyren-2-yloxirane

2,7-divinylpyrene Structure

2,7-divinylpyrene

~73%

2-[7-(oxiran-2-yl)pyren-2-yl]oxirane Structure

2-[7-(oxiran-2-...

4,5,9,10-Tetrahydropyrene Structure

4,5,9,10-Tetrah...

~%

2-[7-(oxiran-2-yl)pyren-2-yl]oxirane Structure

2-[7-(oxiran-2-...

1-[7-(1-hydroxyethyl)pyren-2-yl]ethanol Structure

1-[7-(1-hydroxy...

~%

2-[7-(oxiran-2-yl)pyren-2-yl]oxirane Structure

2-[7-(oxiran-2-...

2,7-diacetylpyrene Structure

2,7-diacetylpyrene

~%

2-[7-(oxiran-2-yl)pyren-2-yl]oxirane Structure

2-[7-(oxiran-2-...

1-(7-acetyl-4,5,9,10-tetrahydropyren-2-yl)ethanone Structure

1-(7-acetyl-4,5...

~%

2-[7-(oxiran-2-yl)pyren-2-yl]oxirane Structure

2-[7-(oxiran-2-...

1-Pyrenecarboxaldehyde Structure

1-Pyrenecarboxa...

dimethylsulphonium methylide Structure

dimethylsulphon...

~90%

1-Oxiranylpyrene Structure

1-Oxiranylpyrene

1-(2-PYRENYL)ETHANOL Structure

1-(2-PYRENYL)ETHANOL

~%

2-pyren-2-yloxirane Structure

2-pyren-2-yloxirane

PYRENE, 4,5-DIHYDRO- Structure

PYRENE, 4,5-DIHYDRO-

~%

2-[7-(oxiran-2-yl)pyren-2-yl]oxirane Structure

2-[7-(oxiran-2-...

4,5,9,10-Tetrahydropyrene Structure

4,5,9,10-Tetrah...

Acetyl chloride Structure

Acetyl chloride

~99%

1-(7-acetyl-4,5,9,10-tetrahydropyren-2-yl)ethanone Structure

1-(7-acetyl-4,5...

PYRENE, 4,5-DIHYDRO- Structure

PYRENE, 4,5-DIHYDRO-

~%

1-(7-acetyl-4,5,9,10-tetrahydropyren-2-yl)ethanone Structure

1-(7-acetyl-4,5...

4-Bromopyrene Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~%

pyrene-4-carbaldehyde Structure

pyrene-4-carbal...