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

Quaternary Salts of Halogenated Pyridines and Quinolines1

CT Bahner, WK Easley, MD Pickens…

Index: Bahner et al. Journal of the American Chemical Society, 1951 , vol. 73, p. 3499

Full Text: HTML

Citation Number: 10

Abstract

Since certain quaternary salts of pyridine and quinoline have been reported to damage sarcoma cells in vivo2 we have prepared similar salts of several halogenated pyridines and quinolines for screening against sarcoma in mice3 and for correlation of biological effects and other properties with structure. were prepared by reaction of a halogenated heterocyclic base with the appropriate organic halide at 30-40'. When the reactants alone did not form ...

2-Chloropyridine Structure

2-Chloropyridine

2,4′-dibromoacetophenone Structure

2,4′-dibromoace...

~%

1-(4-bromophenyl)-2-(2-chloro-2H-pyridin-1-yl)ethanone Structure

1-(4-bromopheny...

2-Bromopyridine Structure

2-Bromopyridine

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

2-(2-bromo-2H-pyridin-1-yl)-1-(4-fluorophenyl)ethanone Structure

2-(2-bromo-2H-p...

3-Iodopyridine Structure

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

1-(4-fluorophenyl)-2-(5-iodopyridin-1-yl)ethanone Structure

1-(4-fluorophen...

2-Chloropyridine Structure

2-Chloropyridine

2-Bromo-4'-iodoacetophenone Structure

2-Bromo-4'-iodo...

~%

2-(2-chloro-2H-pyridin-1-yl)-1-(4-iodophenyl)ethanone Structure

2-(2-chloro-2H-...

3-Bromopyridine Structure

3-Bromopyridine

alpha-(bromomethyl)benzyl alcohol Structure

alpha-(bromomet...

~%

2-(5-bromopyridin-1-yl)-1-phenyl-ethanol Structure

2-(5-bromopyrid...

6-Chloroquinoline Structure

6-Chloroquinoline

1,3-Dibromo-2-propanol Structure

1,3-Dibromo-2-p...

~%

1-bromo-3-(6-chloroquinolin-1-yl)propan-2-ol Structure

1-bromo-3-(6-ch...

3-Bromopyridine Structure

3-Bromopyridine

(2-Bromoethyl)cyclohexane Structure

(2-Bromoethyl)c...

~%

5-bromo-1-(2-cyclohexylethyl)pyridine Structure

5-bromo-1-(2-cy...

3-Bromopyridine Structure

3-Bromopyridine

2-iodo-1-naphthalen-2-ylethanone Structure

2-iodo-1-naphth...

~%

2-(5-bromopyridin-1-yl)-1-naphthalen-2-yl-ethanone Structure

2-(5-bromopyrid...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

2-(3,5-dibromopyridin-1-yl)-1-(4-fluorophenyl)ethanone Structure

2-(3,5-dibromop...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

2,4′-dibromoacetophenone Structure

2,4′-dibromoace...

~%

1-(4-bromophenyl)-2-(3,5-dibromopyridin-1-yl)ethanone Structure

1-(4-bromopheny...

6-Chloroquinoline Structure

6-Chloroquinoline

2,4′-dibromoacetophenone Structure

2,4′-dibromoace...

~%

Quinolinium,1-[2-(4-bromophenyl)-2-oxoethyl]-6-chloro-, bromide (1:1) Structure

Quinolinium,1-[...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

3-Nitrophenacylbromide Structure

3-Nitrophenacyl...

~%

2-(3,5-dibromopyridin-1-yl)-1-(3-nitrophenyl)ethanone Structure

2-(3,5-dibromop...

3-Bromopyridine Structure

3-Bromopyridine

~%

Pyridinium,3-bromo-1-[2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-, bromide (1:1) Structure

Pyridinium,3-br...

6-Chloroquinoline Structure

6-Chloroquinoline

2-BROMO-1-(4-TERT-BUTYL-PHENYL)-ETHANONE Structure

2-BROMO-1-(4-TE...

~%

Quinolinium,6-chloro-1-[2-[4-(1,1-dimethylethyl)phenyl]-2-oxoethyl]-, bromide (1:1) Structure

Quinolinium,6-c...

2-Chloropyridine Structure

2-Chloropyridine

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

Pyridinium,2-chloro-1-[2-(4-chlorophenyl)-2-oxoethyl]-, bromide (1:1) Structure

Pyridinium,2-ch...

3-Bromopyridine Structure

3-Bromopyridine

1-iodo-Decane Structure

~%

5-bromo-1-decyl-pyridine Structure

5-bromo-1-decyl...

3-Bromopyridine Structure

3-Bromopyridine

2-Bromo-1-(2,5-dichlorophenyl)ethanone Structure

2-Bromo-1-(2,5-...

~%

2-(5-bromopyridin-1-yl)-1-(2,5-dichlorophenyl)ethanone Structure

2-(5-bromopyrid...

2-Bromopyridine Structure

2-Bromopyridine

2-Bromo-4'-iodoacetophenone Structure

2-Bromo-4'-iodo...

~%

2-(2-bromo-2H-pyridin-1-yl)-1-(4-iodophenyl)ethanone Structure

2-(2-bromo-2H-p...

3-Bromopyridine Structure

3-Bromopyridine

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

Pyridinium,3-bromo-1-[2-(4-fluorophenyl)-2-oxoethyl]-, bromide (1:1) Structure

Pyridinium,3-br...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

Pyridinium,3,5-dibromo-1-[2-(4-chlorophenyl)-2-oxoethyl]-, bromide (1:1) Structure

Pyridinium,3,5-...

6-Chloroquinoline Structure

6-Chloroquinoline

1-iodo-Decane Structure

~%

6-chloro-1-decyl-quinoline Structure

6-chloro-1-decy...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

2-iodo-1-(5,6,7,8-tetrahydro-[2]naphthyl)-ethanone Structure

2-iodo-1-(5,6,7...

~%

2-(3,5-dibromopyridin-1-yl)-1-tetralin-2-yl-ethanone Structure

2-(3,5-dibromop...

3-Bromopyridine Structure

3-Bromopyridine

Ethyl iodoacetate Structure

Ethyl iodoacetate

~%

ethyl 2-(5-bromopyridin-1-yl)acetate iodide Structure

ethyl 2-(5-brom...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

~%

5-(3-chloro-2-methyl-phenyl)-N-(9,10-dioxoanthracen-2-yl)furan-2-carboxamide Structure

5-(3-chloro-2-m...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

PTP inhibitor 1 Structure

PTP inhibitor 1

~%

2-(3,5-dibromopyridin-1-yl)-1-(4-methoxyphenyl)ethanone Structure

2-(3,5-dibromop...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

p-Bromoacetylbiphenyl Structure

p-Bromoacetylbi...

~%

2-(3,5-dibromopyridin-1-yl)-1-(4-phenylphenyl)ethanone Structure

2-(3,5-dibromop...

3-Bromopyridine Structure

3-Bromopyridine

1,3-Dibromo-2-propanol Structure

1,3-Dibromo-2-p...

~%

1-(3-bromo-1-piperidyl)-3-(3-bromo-6H-pyridin-1-yl)propan-2-ol Structure

1-(3-bromo-1-pi...

3-Bromoquinoline Structure

3-Bromoquinoline

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

2-(3-bromoquinolin-1-yl)-1-(4-fluorophenyl)ethanone Structure

2-(3-bromoquino...

6-Chloroquinoline Structure

6-Chloroquinoline

3-Nitrophenacylbromide Structure

3-Nitrophenacyl...

~%

2-(6-chloroquinolin-1-yl)-1-(3-nitrophenyl)ethanone Structure

2-(6-chloroquin...

6-Chloroquinoline Structure

6-Chloroquinoline

(2-Bromoethyl)benzene Structure

(2-Bromoethyl)b...

~%

2-(1,3-dioxoisoindol-2-yl)-N-(6-methyl-3-prop-2-enyl-benzothiazol-2-ylidene)acetamide Structure

2-(1,3-dioxoiso...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

~%

1-(4-chlorophenyl)-2-(3,5-dibromopyridin-1-yl)propan-1-one Structure

1-(4-chlorophen...

3-Bromopyridine Structure

3-Bromopyridine

PTP inhibitor 1 Structure

PTP inhibitor 1

~%

2-(5-bromopyridin-1-yl)-1-(4-methoxyphenyl)ethanone Structure

2-(5-bromopyrid...

3-Bromopyridine Structure

3-Bromopyridine

Ethanone,2-bromo-1-(4-fluoro-1-naphthalenyl)- Structure

Ethanone,2-brom...

~%

2-(5-bromopyridin-1-yl)-1-(4-fluoronaphthalen-1-yl)ethanone Structure

2-(5-bromopyrid...

6-Chloroquinoline Structure

6-Chloroquinoline

2-Bromo-1-(2-naphthyl)ethanone Structure

2-Bromo-1-(2-na...

~%

2-(6-chloroquinolin-1-yl)-1-naphthalen-2-yl-ethanone Structure

2-(6-chloroquin...

2-Bromopyridine Structure

2-Bromopyridine

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

Pyridinium, 2-bromo-1-[2-(4-chlorophenyl)-2-oxoethyl]-,bromide (1:1) Structure

Pyridinium, 2-b...

6-Chloroquinoline Structure

6-Chloroquinoline

2-bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Structure

2-bromo-1-(5,6,...

~%

2-(6-chloroquinolin-1-yl)-1-tetralin-2-yl-ethanone Structure

2-(6-chloroquin...

3-Bromopyridine Structure

3-Bromopyridine

3-Nitrophenacylbromide Structure

3-Nitrophenacyl...

~%

2-(5-bromopyridin-1-yl)-1-(3-nitrophenyl)ethanone Structure

2-(5-bromopyrid...

6-Chloroquinoline Structure

6-Chloroquinoline

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

1-(4-chlorophenyl)-2-(6-chloroquinolin-1-yl)ethanone Structure

1-(4-chlorophen...

3,5-Dibromopyridine Structure

3,5-Dibromopyridine

2-iodo-1-naphthalen-2-ylethanone Structure

2-iodo-1-naphth...

~%

2-(3,5-dibromopyridin-1-yl)-1-naphthalen-2-yl-ethanone Structure

2-(3,5-dibromop...

2-Bromopyridine Structure

2-Bromopyridine

2-bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Structure

2-bromo-1-(5,6,...

~%

2-(2-bromo-2H-pyridin-1-yl)-1-tetralin-2-yl-ethanone Structure

2-(2-bromo-2H-p...

3-Chloropyridine Structure

3-Chloropyridine

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

2-(5-chloropyridin-1-yl)-1-(4-fluorophenyl)ethanone Structure

2-(5-chloropyri...

3-Bromopyridine Structure

3-Bromopyridine

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

2-(5-bromopyridin-1-yl)-1-(4-chlorophenyl)ethanone Structure

2-(5-bromopyrid...

3-Fluoropyridine Structure

3-Fluoropyridine

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

1-(4-fluorophenyl)-2-(5-fluoropyridin-1-yl)ethanone Structure

1-(4-fluorophen...

6-Chloroquinoline Structure

6-Chloroquinoline

PTP inhibitor 1 Structure

PTP inhibitor 1

~%

2-(6-chloroquinolin-1-yl)-1-(4-methoxyphenyl)ethanone Structure

2-(6-chloroquin...

2-Chloropyridine Structure

2-Chloropyridine

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

2-(2-chloro-2H-pyridin-1-yl)-1-(4-fluorophenyl)ethanone Structure

2-(2-chloro-2H-...