Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl) …

…, JL Johnson, SJ Kesten, DJ McNamara…

Index: Werbel; Cook; Elslager; Hung; Johnson; Kesten; McNamara; Ortwine; Worth Journal of Medicinal Chemistry, 1986 , vol. 29, # 6 p. 924 - 939

Full Text: HTML

Citation Number: 51

Abstract

A series of 54 (7-chloro-4-quinolinyl) amino]-3-[(alkylamino) methyl][l, l'-biphenyl]-2-ols and N”-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the &nitro [l, l'-bipheny1]-2-01~, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino) methyl]-6-hydroxy [l, l'-biphenyl]-3-yl] acetamides and final condensation with 4, 7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship ...

 Related Synthetic Route
METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

2-(2-Fluorophenyl)acetic acid Structure

451-82-1

2-(2-Fluorophen...

~96%

2-Fluorophenylacetone Structure

2836-82-0

2-Fluorophenyla...

1-Chloro-4-iodobenzene Structure

637-87-6

1-Chloro-4-iodo...

~%

Teboquine Structure

74129-03-6

Teboquine

iodoanisole Structure

529-28-2

iodoanisole

~%

Teboquine Structure

74129-03-6

Teboquine

4'-chloro-[1,1'-Biphenyl]-2-ol Structure

64181-76-6

4'-chloro-[1,1'...

~%

Teboquine Structure

74129-03-6

Teboquine

1-chloro-4-(2-methoxyphenyl)benzene Structure

53824-23-0

1-chloro-4-(2-m...

~%

Teboquine Structure

74129-03-6

Teboquine

2-(4-chlorophenyl)-2,5-cyclohexadiene-1,4-dione 4-oxime Structure

79287-41-5

2-(4-chlorophen...

~%

Teboquine Structure

74129-03-6

Teboquine

5-amino-4'-chloro[1,1'-biphenyl]-2-ol Structure

79287-36-8

5-amino-4'-chlo...

~%

Teboquine Structure

74129-03-6

Teboquine

N-(4'-chloro-6-hydroxy[1,1'-biphenyl]-3-yl)acetamide Structure

79287-24-4

N-(4'-chloro-6-...

~%

Teboquine Structure

74129-03-6

Teboquine

3-(4'-chlorophenyl)-4-hydroxy-5-[(tert-butylamino)methyl]acetanilide Structure

79287-26-6

3-(4'-chlorophe...

~%

Teboquine Structure

74129-03-6

Teboquine

4,7-Dichloroquinoline Structure

86-98-6

4,7-Dichloroqui...

5-amino-3-(t-butylaminomethyl)-4'-chlorobiphenyl-2-ol Structure

79287-52-8

5-amino-3-(t-bu...

~%

Teboquine Structure

74129-03-6

Teboquine

2-Phenylphenol Structure

90-43-7

2-Phenylphenol

~%

[1,1'-Biphenyl]-2-ol,5-amino- Structure

19434-42-5

[1,1'-Biphenyl]...

2-PHENYL-[1,4]BENZOQUINONE 4-OXIME Structure

36697-36-6

2-PHENYL-[1,4]B...

~84%

[1,1'-Biphenyl]-2-ol,5-amino- Structure

19434-42-5

[1,1'-Biphenyl]...

METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

3-Fluorophenylacetic acid Structure

331-25-9

3-Fluorophenyla...

~97%

3-Fluorophenylacetone Structure

1737-19-5

3-Fluorophenyla...

1-Chloro-4-iodobenzene Structure

637-87-6

1-Chloro-4-iodo...

iodoanisole Structure

529-28-2

iodoanisole

~24%

1-chloro-4-(2-methoxyphenyl)benzene Structure

53824-23-0

1-chloro-4-(2-m...

1-Chloro-4-iodobenzene Structure

637-87-6

1-Chloro-4-iodo...

~%

[1,1'-Biphenyl]-2-ol,4'-chloro-5-[(7-chloro-4-quinolinyl)amino]-3-[(diethylamino)methyl]- Structure

79286-94-5

[1,1'-Biphenyl]...

iodoanisole Structure

529-28-2

iodoanisole

~%

[1,1'-Biphenyl]-2-ol,4'-chloro-5-[(7-chloro-4-quinolinyl)amino]-3-[(diethylamino)methyl]- Structure

79286-94-5

[1,1'-Biphenyl]...

4'-chloro-[1,1'-Biphenyl]-2-ol Structure

64181-76-6

4'-chloro-[1,1'...

~%

[1,1'-Biphenyl]-2-ol,4'-chloro-5-[(7-chloro-4-quinolinyl)amino]-3-[(diethylamino)methyl]- Structure

79286-94-5

[1,1'-Biphenyl]...

1-chloro-4-(2-methoxyphenyl)benzene Structure

53824-23-0

1-chloro-4-(2-m...

~%

[1,1'-Biphenyl]-2-ol,4'-chloro-5-[(7-chloro-4-quinolinyl)amino]-3-[(diethylamino)methyl]- Structure

79286-94-5

[1,1'-Biphenyl]...

2-(4-chlorophenyl)-2,5-cyclohexadiene-1,4-dione 4-oxime Structure

79287-41-5

2-(4-chlorophen...

~%

[1,1'-Biphenyl]-2-ol,4'-chloro-5-[(7-chloro-4-quinolinyl)amino]-3-[(diethylamino)methyl]- Structure

79286-94-5

[1,1'-Biphenyl]...

5-amino-4'-chloro[1,1'-biphenyl]-2-ol Structure

79287-36-8

5-amino-4'-chlo...

~%

[1,1'-Biphenyl]-2-ol,4'-chloro-5-[(7-chloro-4-quinolinyl)amino]-3-[(diethylamino)methyl]- Structure

79286-94-5

[1,1'-Biphenyl]...

N-(4'-chloro-6-hydroxy[1,1'-biphenyl]-3-yl)acetamide Structure

79287-24-4

N-(4'-chloro-6-...

~%

[1,1'-Biphenyl]-2-ol,4'-chloro-5-[(7-chloro-4-quinolinyl)amino]-3-[(diethylamino)methyl]- Structure

79286-94-5

[1,1'-Biphenyl]...

3-(4'-chlorophenyl)-4-hydroxy-5-[(diethylamino)methyl]acetanilide Structure

79287-25-5

3-(4'-chlorophe...

~%

[1,1'-Biphenyl]-2-ol,4'-chloro-5-[(7-chloro-4-quinolinyl)amino]-3-[(diethylamino)methyl]- Structure

79286-94-5

[1,1'-Biphenyl]...

4,7-Dichloroquinoline Structure

86-98-6

4,7-Dichloroqui...

5-amino-4'-chloro-3-diethylaminomethylbiphenyl-2-ol Structure

130806-40-5

5-amino-4'-chlo...

~%

[1,1'-Biphenyl]-2-ol,4'-chloro-5-[(7-chloro-4-quinolinyl)amino]-3-[(diethylamino)methyl]- Structure

79286-94-5

[1,1'-Biphenyl]...

4-Methoxyphenylacetone Structure

122-84-9

4-Methoxyphenyl...

Sodium nitromalonaldehyde Structure

34461-00-2

Sodium nitromal...

~38%

4''-METHOXY-5-NITRO-1,1''-BIPHENYL-2-OL Structure

63801-89-8

4''-METHOXY-5-N...

4-(Methylthio)benzaldehyde Structure

3446-89-7

4-(Methylthio)b...

~%

1-(4-methylsulfanylphenyl)propan-2-one Structure

88356-92-7

1-(4-methylsulf...

METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

4-Fluorophenylacetic acid Structure

405-50-5

4-Fluorophenyla...

~94%

4-Fluorophenylacetone Structure

459-03-0

4-Fluorophenyla...


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