Structure-activity relationships of antimalarial indolo [3, 2-c] quinolines [1, 2]

LM Werbel, SJ Kesten, WR Turner

Index: Werbel, L. M.; Kesten, S. J.; Turner, W. R. European Journal of Medicinal Chemistry, 1993 , vol. 28, # 11 p. 837 - 852

Full Text: HTML

Citation Number: 24

Abstract

Abstract Structure-activity relationships have been ascertained and chemical methodology developed for a series of antimalarial 3-chloroindolo [3, 2-c] quinoline-5-oxides. The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3. Substitution at positions 7, 8, 9, 10 is not essential, although the most potent analog in our studies was the 8-nitro compound 4vv.

 Related Synthetic Route
Methyl N-(4-methoxyphenyl)-beta-alaninate Structure

42313-52-0

Methyl N-(4-met...

~%

4(1H)-Quinolinone,2,3-dihydro-6-methoxy- Structure

3835-21-0

4(1H)-Quinolino...

methyl N-tosyl-3-(4-methoxyanilino)propionate Structure

637038-53-0

methyl N-tosyl-...

~%

4(1H)-Quinolinone,2,3-dihydro-6-methoxy- Structure

3835-21-0

4(1H)-Quinolino...

methyl N-(3-chlorophenyl)-β-alaninate Structure

42313-47-3

methyl N-(3-chl...

~%

11H-Indolo[3,2-c]quinolin-9-amine, 3-chloro-N,N-diethyl-8-methoxy- Structure

34374-22-6

11H-Indolo[3,2-...

3-[(3-chlorophenyl)-(4-methylphenyl)sulfonyl-amino]propanoic acid Structure

66737-56-2

3-[(3-chlorophe...

~%

11H-Indolo[3,2-c]quinolin-9-amine, 3-chloro-N,N-diethyl-8-methoxy- Structure

34374-22-6

11H-Indolo[3,2-...

3-Chloroaniline Structure

108-42-9

3-Chloroaniline

~%

11H-Indolo[3,2-c]quinolin-9-amine, 3-chloro-N,N-diethyl-8-methoxy- Structure

34374-22-6

11H-Indolo[3,2-...

4(1H)-Quinolinone,7-chloro-2,3-dihydro-1-[(4-methylphenyl)sulfonyl]- Structure

66820-85-7

4(1H)-Quinolino...

~%

11H-Indolo[3,2-c]quinolin-9-amine, 3-chloro-N,N-diethyl-8-methoxy- Structure

34374-22-6

11H-Indolo[3,2-...

Methyl N-phenyl-β-alaninate Structure

21911-84-2

Methyl N-phenyl...

~%

11H-indolo[3,2-c]quinoline Structure

239-09-8

11H-indolo[3,2-...

4(1H)-Quinolinone,2,3-dihydro-1-[(4-methylphenyl)sulfonyl]- Structure

14278-37-6

4(1H)-Quinolino...

~%

11H-indolo[3,2-c]quinoline Structure

239-09-8

11H-indolo[3,2-...

methyl 3-[(4-methylphenyl)sulfonyl-phenyl-amino]propanoate Structure

17266-98-7

methyl 3-[(4-me...

~%

11H-indolo[3,2-c]quinoline Structure

239-09-8

11H-indolo[3,2-...

b-Alanine,N-[(4-methylphenyl)sulfonyl]-N-phenyl- Structure

65148-06-3

b-Alanine,N-[(4...

~%

11H-indolo[3,2-c]quinoline Structure

239-09-8

11H-indolo[3,2-...

Structure

74497-02-2

~%

11H-indolo[3,2-c]quinoline Structure

239-09-8

11H-indolo[3,2-...

2,3-Dihydro-1H-quinolin-4-one Structure

4295-36-7

2,3-Dihydro-1H-...

Phenylhydrazine hydrochloride Structure

59-88-1

Phenylhydrazine...

~%

11H-indolo[3,2-c]quinoline Structure

239-09-8

11H-indolo[3,2-...

3-[(3-chlorophenyl)-(4-methylphenyl)sulfonyl-amino]propanoic acid Structure

66737-56-2

3-[(3-chlorophe...

~%

7-Chloro-2,3-dihydro-4-quinolone Structure

21617-15-2

7-Chloro-2,3-di...

methyl N-(3-chlorophenyl)-β-alaninate Structure

42313-47-3

methyl N-(3-chl...

~%

7-Chloro-2,3-dihydro-4-quinolone Structure

21617-15-2

7-Chloro-2,3-di...

3-Chloroaniline Structure

108-42-9

3-Chloroaniline

~%

7-Chloro-2,3-dihydro-4-quinolone Structure

21617-15-2

7-Chloro-2,3-di...

3-[(3-chlorophenyl)-(4-methylphenyl)sulfonyl-amino]propanoic acid Structure

66737-56-2

3-[(3-chlorophe...

~%

7-Chloro-2,3-dihydro-4-quinolone Structure

21617-15-2

7-Chloro-2,3-di...

5-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

21617-16-3

5-CHLORO-2,3-DI...

1-(1-(4-chloro-2-nitrophenyl)ethylidene)-2-phenylhydrazine Structure

65287-66-3

1-(1-(4-chloro-...

~33%

2-(4-chloro-2-nitrophenyl)-1H-indole Structure

65287-40-3

2-(4-chloro-2-n...

2′-Nitroacetophenone Structure

577-59-3

2′-Nitroacetophenone

~%

2-(2-nitrophenyl)-1H-indole Structure

59050-53-2

2-(2-nitropheny...

methyl N-(3-chlorophenyl)-β-alaninate Structure

42313-47-3

methyl N-(3-chl...

~%

3-[(3-chlorophenyl)-(4-methylphenyl)sulfonyl-amino]propanoic acid Structure

66737-56-2

3-[(3-chlorophe...

3-Chloroaniline Structure

108-42-9

3-Chloroaniline

~%

3-[(3-chlorophenyl)-(4-methylphenyl)sulfonyl-amino]propanoic acid Structure

66737-56-2

3-[(3-chlorophe...

4-(METHYLMERCAPTO)ANILINE HYDROCHLORIDE Structure

39870-00-3

4-(METHYLMERCAP...

~%

(4-(METHYLTHIO)PHENYL)HYDRAZINE Structure

51304-69-9

(4-(METHYLTHIO)...

4(1H)-Quinolinone,2,3-dihydro-6-methoxy- Structure

3835-21-0

4(1H)-Quinolino...

Phenylhydrazine hydrochloride Structure

59-88-1

Phenylhydrazine...

~28%

2-methoxy-11H-indolo[3,2-c]quinoline Structure

4295-45-8

2-methoxy-11H-i...

Methyl N-(4-methoxyphenyl)-beta-alaninate Structure

42313-52-0

Methyl N-(4-met...

~%

2-methoxy-11H-indolo[3,2-c]quinoline Structure

4295-45-8

2-methoxy-11H-i...

6-methoxy-1-tosyl-2,3-dihydroquinolin-4(1H)-one Structure

75227-41-7

6-methoxy-1-tos...

~%

2-methoxy-11H-indolo[3,2-c]quinoline Structure

4295-45-8

2-methoxy-11H-i...

methyl N-tosyl-3-(4-methoxyanilino)propionate Structure

637038-53-0

methyl N-tosyl-...

~%

2-methoxy-11H-indolo[3,2-c]quinoline Structure

4295-45-8

2-methoxy-11H-i...

p-Anisidine Structure

104-94-9

p-Anisidine

~%

2-methoxy-11H-indolo[3,2-c]quinoline Structure

4295-45-8

2-methoxy-11H-i...

Methyl N-phenyl-β-alaninate Structure

21911-84-2

Methyl N-phenyl...

~%

b-Alanine,N-[(4-methylphenyl)sulfonyl]-N-phenyl- Structure

65148-06-3

b-Alanine,N-[(4...

methyl N-(3-chlorophenyl)-β-alaninate Structure

42313-47-3

methyl N-(3-chl...

~%

4(1H)-Quinolinone,7-chloro-2,3-dihydro-1-[(4-methylphenyl)sulfonyl]- Structure

66820-85-7

4(1H)-Quinolino...

3-Chloroaniline Structure

108-42-9

3-Chloroaniline

~%

4(1H)-Quinolinone,7-chloro-2,3-dihydro-1-[(4-methylphenyl)sulfonyl]- Structure

66820-85-7

4(1H)-Quinolino...

Methyl N-(3-bromophenyl)-β-alaninate Structure

857576-77-3

Methyl N-(3-bro...

~%

7-Bromo-2,3-dihydro-1H-quinolin-4-one Structure

114417-34-4

7-Bromo-2,3-dih...

3-Bromoaniline Structure

591-19-5

3-Bromoaniline

~%

7-Bromo-2,3-dihydro-1H-quinolin-4-one Structure

114417-34-4

7-Bromo-2,3-dih...

4(1H)-Quinolinone,2,3-dihydro-1-[(4-methylphenyl)sulfonyl]- Structure

14278-37-6

4(1H)-Quinolino...

~83%

2,3-Dihydro-1H-quinolin-4-one Structure

4295-36-7

2,3-Dihydro-1H-...

2-Chloroaniline Structure

95-51-2

2-Chloroaniline

~%

8-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

21617-11-8

8-CHLORO-2,3-DI...

N-(2-chlorophenyl)-β-alanine methyl ester Structure

51228-54-7

N-(2-chlorophen...

~%

8-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

21617-11-8

8-CHLORO-2,3-DI...

3-[(3-chlorophenyl)-(4-methylphenyl)sulfonyl-amino]propanoic acid Structure

66737-56-2

3-[(3-chlorophe...

~%

7-Chloro-2,3-dihydro-4-quinolone Structure

21617-15-2

7-Chloro-2,3-di...

5-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

21617-16-3

5-CHLORO-2,3-DI...

methyl N-(3-chlorophenyl)-β-alaninate Structure

42313-47-3

methyl N-(3-chl...

~%

5-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

21617-16-3

5-CHLORO-2,3-DI...


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