Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines

…, H Johnston, SG Wood, AP Vinogradoff…

Index: Markley; Tong; Dulworth; Steward; Goralski; Johnston; Wood; Vinogradoff; Bargar Journal of Medicinal Chemistry, 1986 , vol. 29, # 3 p. 427 - 433

Full Text: HTML

Citation Number: 50

Abstract

Phenoxybenzenes and phenoxypyridines were prepared and tested for the effect of substituents on antipicornavirus activity. The most active compound, 2-(3, 4- dichlorophenoxy)-5-nitrobenzonitrile (8), demonstrated broad-spectrum antipicornavirus activity. Compound 8 and several analogues each given orally prior to and during infection protected mice against an otherwise lethal challenge with coxsackievirus A21.

 Related Synthetic Route
(6-Chloro-3-pyridinyl)acetonitrile Structure

33252-28-7

(6-Chloro-3-pyr...

4-Chlorophenol Structure

106-48-9

4-Chlorophenol

~%

6-(4-Chlorophenoxy)nicotinonitrile Structure

99902-70-2

6-(4-Chlorophen...

(6-Chloro-3-pyridinyl)acetonitrile Structure

33252-28-7

(6-Chloro-3-pyr...

4-Hydroxyacetophenone Structure

99-93-4

4-Hydroxyacetop...

~%

6-(4-acetylphenoxy)pyridine-3-carbonitrile Structure

99902-71-3

6-(4-acetylphen...

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

2-Chloro-6-cyanopyridine Structure

33252-29-8

2-Chloro-6-cyan...

~%

6-(3,4-dichlorophenoxy)pyridine-2-carbonitrile Structure

99902-95-1

6-(3,4-dichloro...

(6-Chloro-3-pyridinyl)acetonitrile Structure

33252-28-7

(6-Chloro-3-pyr...

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

~%

6-(3,4-dichlorophenoxy)pyridine-3-carbonitrile Structure

99902-73-5

6-(3,4-dichloro...

2-(3,4-dichlorophenoxy)-5-nitropyridine Structure

25935-29-9

2-(3,4-dichloro...

~82%

6-(3,4-dichlorophenoxy)pyridin-3-amine Structure

25935-30-2

6-(3,4-dichloro...

2-Chloro-5-nitropyridine Structure

4548-45-2

2-Chloro-5-nitr...

~%

6-(3,4-dichlorophenoxy)pyridin-3-amine Structure

25935-30-2

6-(3,4-dichloro...

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

~%

6-(3,4-dichlorophenoxy)pyridin-3-amine Structure

25935-30-2

6-(3,4-dichloro...

2-Chloro-5-bromopyridine Structure

53939-30-3

2-Chloro-5-brom...

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

~%

5-bromo-2-(3,4-dichlorophenoxy)pyridine Structure

99902-96-2

5-bromo-2-(3,4-...

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

~%

4-Chloroisophthalonitrile Structure

4387-30-8

4-Chloroisophth...

5-Amino-2-chlorobenzonitrile Structure

35747-58-1

5-Amino-2-chlor...

Sodium cyanide Structure

143-33-9

Sodium cyanide

~%

4-Chloroisophthalonitrile Structure

4387-30-8

4-Chloroisophth...

(6-Chloro-3-pyridinyl)acetonitrile Structure

33252-28-7

(6-Chloro-3-pyr...

p-Cresol Structure

106-44-5

p-Cresol

~%

6-(4-methylphenoxy)pyridine-3-carbonitrile Structure

99902-75-7

6-(4-methylphen...

2-Chloro-5-nitropyridine Structure

4548-45-2

2-Chloro-5-nitr...

~%

6-(3,4-dichlorophenoxy)pyridine-3-sulfonic acid Structure

99902-98-4

6-(3,4-dichloro...

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

~%

6-(3,4-dichlorophenoxy)pyridine-3-sulfonic acid Structure

99902-98-4

6-(3,4-dichloro...

2-(3,4-dichlorophenoxy)-5-nitropyridine Structure

25935-29-9

2-(3,4-dichloro...

~%

6-(3,4-dichlorophenoxy)pyridine-3-sulfonic acid Structure

99902-98-4

6-(3,4-dichloro...

6-(3,4-dichlorophenoxy)pyridin-3-amine Structure

25935-30-2

6-(3,4-dichloro...

~%

6-(3,4-dichlorophenoxy)pyridine-3-sulfonic acid Structure

99902-98-4

6-(3,4-dichloro...

3-Chlorophenol Structure

108-43-0

3-Chlorophenol

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

~%

2-(3-chlorophenoxy)-5-nitrobenzonitrile Structure

99902-76-8

2-(3-chlorophen...

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

2-Chlorophenol Structure

95-57-8

2-Chlorophenol

~%

2-(2-chlorophenoxy)-5-nitrobenzonitrile Structure

99902-77-9

2-(2-chlorophen...

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

2-Bromophenol Structure

95-56-7

2-Bromophenol

~%

2-(2-bromophenoxy)-5-nitrobenzonitrile Structure

99902-78-0

2-(2-bromopheno...

2-Chlorobenzonitrile Structure

873-32-5

2-Chlorobenzonitrile

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

~%

2-(3,4-dichlorophenoxy)benzonitrile Structure

99902-85-9

2-(3,4-dichloro...

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

4-Chloroisophthalonitrile Structure

4387-30-8

4-Chloroisophth...

~71%

4-(3,4-dichlorophenoxy)benzene-1,3-dicarbonitrile Structure

99902-86-0

4-(3,4-dichloro...

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

~%

4-(3,4-dichlorophenoxy)benzene-1,3-dicarbonitrile Structure

99902-86-0

4-(3,4-dichloro...

5-Amino-2-chlorobenzonitrile Structure

35747-58-1

5-Amino-2-chlor...

~%

4-(3,4-dichlorophenoxy)benzene-1,3-dicarbonitrile Structure

99902-86-0

4-(3,4-dichloro...

2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile Structure

78940-62-2

2-(3,4-dichloro...

~88%

5-amino-2-(3,4-dichlorophenoxy)benzonitrile Structure

99902-87-1

5-amino-2-(3,4-...

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

Mequinol Structure

150-76-5

Mequinol

~%

2-(4-methoxyphenoxy)-5-nitrobenzonitrile Structure

99902-79-1

2-(4-methoxyphe...

p-Cresol Structure

106-44-5

p-Cresol

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

~%

2-(4-methylphenoxy)-5-nitrobenzonitrile Structure

99902-81-5

2-(4-methylphen...

Acetyl chloride Structure

75-36-5

Acetyl chloride

5-amino-2-(3,4-dichlorophenoxy)benzonitrile Structure

99902-87-1

5-amino-2-(3,4-...

~29%

N-[3-cyano-4-(3,4-dichlorophenoxy)phenyl]acetamide Structure

99902-88-2

N-[3-cyano-4-(3...

2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile Structure

78940-62-2

2-(3,4-dichloro...

~%

N-[3-cyano-4-(3,4-dichlorophenoxy)phenyl]acetamide Structure

99902-88-2

N-[3-cyano-4-(3...

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

4-Hydroxybenzophenone Structure

1137-42-4

4-Hydroxybenzop...

~%

2-(4-benzoylphenoxy)-5-nitrobenzonitrile Structure

78940-72-4

2-(4-benzoylphe...

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

4-Hydroxybenzonitrile Structure

767-00-0

4-Hydroxybenzon...

~%

2-(4-cyanophenoxy)-5-nitrobenzonitrile Structure

99902-82-6

2-(4-cyanopheno...

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

2,5-Dichlorobenzonitrile Structure

21663-61-6

2,5-Dichloroben...

~%

5-chloro-2-(3,4-dichlorophenoxy)benzonitrile Structure

99902-89-3

5-chloro-2-(3,4...

p-Cresol Structure

106-44-5

p-Cresol

4-Fluorophenyl methyl sulfone Structure

455-15-2

4-Fluorophenyl ...

~%

1-methyl-4-(4-methylsulfonylphenoxy)benzene Structure

99902-90-6

1-methyl-4-(4-m...

3-Chlorophenol Structure

108-43-0

3-Chlorophenol

4-Fluorophenyl methyl sulfone Structure

455-15-2

4-Fluorophenyl ...

~%

1-chloro-3-(4-methylsulfonylphenoxy)benzene Structure

99902-91-7

1-chloro-3-(4-m...

1-Naphthalenol Structure

90-15-3

1-Naphthalenol

2-Chloro-5-nitrobenzonitrile Structure

16588-02-6

2-Chloro-5-nitr...

~%

2-naphthalen-1-yloxy-5-nitrobenzonitrile Structure

99902-84-8

2-naphthalen-1-...

2-Chloro-3-cyanopyridine Structure

6602-54-6

2-Chloro-3-cyan...

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

~%

2-(3,4-dichlorophenoxy)pyridine-3-carbonitrile Structure

99902-93-9

2-(3,4-dichloro...

4-Chlorobenzonitrile Structure

623-03-0

4-Chlorobenzonitrile

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

~%

4-(3,4-dichlorophenoxy)benzonitrile Structure

99922-95-9

4-(3,4-dichloro...

2-Chloro-4-cyanopyridine Structure

33252-30-1

2-Chloro-4-cyan...

3,4-Dichlorophenol Structure

95-77-2

3,4-Dichlorophenol

~%

2-(3,4-dichlorophenoxy)pyridine-4-carbonitrile Structure

99902-94-0

2-(3,4-dichloro...


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