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

2, 4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 11. Quinolylmethyl analogs with basic substituents conveying specificity

SE Davis, BS Rauckman, JH Chan…

Index: Davis, Steven E.; Rauckman, Barbara S.; Chan, Joseph H.; Roth, Barbara Journal of Medicinal Chemistry, 1989 , vol. 32, # 8 p. 1936 - 1942

Full Text: HTML

Citation Number: 18

Abstract

A series of nine 2, 4-diamino-5-[6-(or 7-) quinolylmethyl] pyrimidines has been prepared by condensations of qui-nolinecarboxaldehydes with 0-anilinopropionitriles, followed by treatment with guanidine. All compounds had basic or methoxy substituents at the 2-or 4- positions of the quinoline ring. All of the 6-quinolylmethyl derivatives were highly inhibitory against Escherichia coli dihydrofolate reductase (DHFR), provided that an &substituent ...

6-bromo-8-methoxy-2-methyl-4-quinolone Structure

6-bromo-8-metho...

~94%

6-bromo-4-chloro-8-methoxy-2-methylquinoline Structure

6-bromo-4-chlor...

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4-Bromo-o-anisidine Structure

4-Bromo-o-anisidine

~%

6-bromo-4-chloro-8-methoxy-2-methylquinoline Structure

6-bromo-4-chlor...

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2-Anisidine Structure

~%

6-bromo-4-chloro-8-methoxy-2-methylquinoline Structure

6-bromo-4-chlor...

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ethyl 3-(4-bromo-2-methoxyphenyl)iminobutanoate Structure

ethyl 3-(4-brom...

~%

6-bromo-4-chloro-8-methoxy-2-methylquinoline Structure

6-bromo-4-chlor...

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Sodium Methylate Structure

Sodium Methylate

6-bromo-4-chloro-8-methoxy-2-methylquinoline Structure

6-bromo-4-chlor...

~87%

6-bromo-4,8-dimethoxy-2-methylquinoline Structure

6-bromo-4,8-dim...

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4-Bromo-o-anisidine Structure

4-Bromo-o-anisidine

~%

6-bromo-4,8-dimethoxy-2-methylquinoline Structure

6-bromo-4,8-dim...

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2-Anisidine Structure

~%

6-bromo-4,8-dimethoxy-2-methylquinoline Structure

6-bromo-4,8-dim...

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6-bromo-8-methoxy-2-methyl-4-quinolone Structure

6-bromo-8-metho...

~%

6-bromo-4,8-dimethoxy-2-methylquinoline Structure

6-bromo-4,8-dim...

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ethyl 3-(4-bromo-2-methoxyphenyl)iminobutanoate Structure

ethyl 3-(4-brom...

~%

6-bromo-4,8-dimethoxy-2-methylquinoline Structure

6-bromo-4,8-dim...

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4-Bromo-o-anisidine Structure

4-Bromo-o-anisidine

~%

4,8-dimethoxy-2-methylquinoline-6-carbaldehyde Structure

4,8-dimethoxy-2...

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2-Anisidine Structure

~%

4,8-dimethoxy-2-methylquinoline-6-carbaldehyde Structure

4,8-dimethoxy-2...

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6-bromo-8-methoxy-2-methyl-4-quinolone Structure

6-bromo-8-metho...

~%

4,8-dimethoxy-2-methylquinoline-6-carbaldehyde Structure

4,8-dimethoxy-2...

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ethyl 3-(4-bromo-2-methoxyphenyl)iminobutanoate Structure

ethyl 3-(4-brom...

~%

4,8-dimethoxy-2-methylquinoline-6-carbaldehyde Structure

4,8-dimethoxy-2...

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N,N-Dimethylformamide Structure

N,N-Dimethylfor...

6-bromo-4,8-dimethoxy-2-methylquinoline Structure

6-bromo-4,8-dim...

~%

4,8-dimethoxy-2-methylquinoline-6-carbaldehyde Structure

4,8-dimethoxy-2...

6-formyl-4,8-dimethoxy-2-(n-pentyl)quinoline Structure

6-formyl-4,8-di...

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n-Butyllithium Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

6-bromo-4,8-dimethoxy-2-methylquinoline Structure

6-bromo-4,8-dim...

~%

4,8-dimethoxy-2-methylquinoline-6-carbaldehyde Structure

4,8-dimethoxy-2...

Detail Learn More

N-(4-bromo-2-methylphenyl)-3-oxobutanamide Structure

N-(4-bromo-2-me...

~62%

6-bromo-4,8-dimethyl-1H-quinolin-2-one Structure

6-bromo-4,8-dim...

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4-Bromo-2-methylaniline Structure

4-Bromo-2-methy...

~%

6-bromo-4,8-dimethyl-1H-quinolin-2-one Structure

6-bromo-4,8-dim...

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6-bromo-4-chloro-8-methoxy-2-methylquinoline Structure

6-bromo-4-chlor...

~%

4,8-dimethoxy-2-methylquinoline-6-carbaldehyde Structure

4,8-dimethoxy-2...

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4-Bromo-o-anisidine Structure

4-Bromo-o-anisidine

~%

5-[(4,8-dimethoxy-2-methylquinolin-6-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(4,8-dimetho...

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2-Anisidine Structure

~%

5-[(4,8-dimethoxy-2-methylquinolin-6-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(4,8-dimetho...

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6-bromo-4-chloro-8-methoxy-2-methylquinoline Structure

6-bromo-4-chlor...

~%

5-[(4,8-dimethoxy-2-methylquinolin-6-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(4,8-dimetho...

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6-bromo-8-methoxy-2-methyl-4-quinolone Structure

6-bromo-8-metho...

~%

5-[(4,8-dimethoxy-2-methylquinolin-6-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(4,8-dimetho...

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ethyl 3-(4-bromo-2-methoxyphenyl)iminobutanoate Structure

ethyl 3-(4-brom...

~%

5-[(4,8-dimethoxy-2-methylquinolin-6-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(4,8-dimetho...

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6-bromo-4,8-dimethoxy-2-methylquinoline Structure

6-bromo-4,8-dim...

~%

5-[(4,8-dimethoxy-2-methylquinolin-6-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(4,8-dimetho...

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4,8-dimethoxy-2-methylquinoline-6-carbaldehyde Structure

4,8-dimethoxy-2...

~%

5-[(4,8-dimethoxy-2-methylquinolin-6-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(4,8-dimetho...

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Dimethylamine Structure

6-bromo-4-chloro-8-methoxy-2-methylquinoline Structure

6-bromo-4-chlor...

~87%

6-bromo-8-methoxy-N,N,2-trimethylquinolin-4-amine Structure

6-bromo-8-metho...

Learn More

4-Bromo-o-anisidine Structure

4-Bromo-o-anisidine

~%

6-bromo-8-methoxy-N,N,2-trimethylquinolin-4-amine Structure

6-bromo-8-metho...

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2-Anisidine Structure

~%

6-bromo-8-methoxy-N,N,2-trimethylquinolin-4-amine Structure

6-bromo-8-metho...

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6-bromo-8-methoxy-2-methyl-4-quinolone Structure

6-bromo-8-metho...

~%

6-bromo-8-methoxy-N,N,2-trimethylquinolin-4-amine Structure

6-bromo-8-metho...

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ethyl 3-(4-bromo-2-methoxyphenyl)iminobutanoate Structure

ethyl 3-(4-brom...

~%

6-bromo-8-methoxy-N,N,2-trimethylquinolin-4-amine Structure

6-bromo-8-metho...

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6-bromo-4,8-dimethyl-1H-quinolin-2-one Structure

6-bromo-4,8-dim...

~99%

6-bromo-2-chloro-4,8-dimethylquinoline Structure

6-bromo-2-chlor...

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4-Bromo-2-methylaniline Structure

4-Bromo-2-methy...

~%

6-bromo-2-chloro-4,8-dimethylquinoline Structure

6-bromo-2-chlor...

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N-(4-bromo-2-methylphenyl)-3-oxobutanamide Structure

N-(4-bromo-2-me...

~%

6-bromo-2-chloro-4,8-dimethylquinoline Structure

6-bromo-2-chlor...

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4-Bromo-2-methylaniline Structure

4-Bromo-2-methy...

~%

4-(6-bromo-4,8-dimethylquinolin-2-yl)morpholine Structure

4-(6-bromo-4,8-...

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morpholine Structure

6-bromo-2-chloro-4,8-dimethylquinoline Structure

6-bromo-2-chlor...

~96%

4-(6-bromo-4,8-dimethylquinolin-2-yl)morpholine Structure

4-(6-bromo-4,8-...

Learn More

6-bromo-4,8-dimethyl-1H-quinolin-2-one Structure

6-bromo-4,8-dim...

~%

4-(6-bromo-4,8-dimethylquinolin-2-yl)morpholine Structure

4-(6-bromo-4,8-...

Learn More

N-(4-bromo-2-methylphenyl)-3-oxobutanamide Structure

N-(4-bromo-2-me...

~%

4-(6-bromo-4,8-dimethylquinolin-2-yl)morpholine Structure

4-(6-bromo-4,8-...

Learn More

4-Bromo-o-anisidine Structure

4-Bromo-o-anisidine

~%

4-(dimethylamino)-8-methoxy-2-methylquinoline-6-carbaldehyde Structure

4-(dimethylamin...

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2-Anisidine Structure

~%

4-(dimethylamino)-8-methoxy-2-methylquinoline-6-carbaldehyde Structure

4-(dimethylamin...

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6-bromo-4-chloro-8-methoxy-2-methylquinoline Structure

6-bromo-4-chlor...

~%

4-(dimethylamino)-8-methoxy-2-methylquinoline-6-carbaldehyde Structure

4-(dimethylamin...

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6-bromo-8-methoxy-2-methyl-4-quinolone Structure

6-bromo-8-metho...

~%

4-(dimethylamino)-8-methoxy-2-methylquinoline-6-carbaldehyde Structure

4-(dimethylamin...

Learn More

ethyl 3-(4-bromo-2-methoxyphenyl)iminobutanoate Structure

ethyl 3-(4-brom...

~%

4-(dimethylamino)-8-methoxy-2-methylquinoline-6-carbaldehyde Structure

4-(dimethylamin...

Learn More

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

6-bromo-8-methoxy-N,N,2-trimethylquinolin-4-amine Structure

6-bromo-8-metho...

~%

4-(dimethylamino)-8-methoxy-2-methylquinoline-6-carbaldehyde Structure

4-(dimethylamin...

4-(dimethylamino)-8-methoxy-2-pentylquinoline-6-carbaldehyde Structure

4-(dimethylamin...

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n-Butyllithium Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

6-bromo-8-methoxy-N,N,2-trimethylquinolin-4-amine Structure

6-bromo-8-metho...

~%

4-(dimethylamino)-8-methoxy-2-methylquinoline-6-carbaldehyde Structure

4-(dimethylamin...

Detail Learn More

6-Bromo-2-chloro-4-methylquinoline Structure

6-Bromo-2-chlor...

Dimethylamine Structure

~71%

6-bromo-N,N,4-trimethylquinolin-2-amine Structure

6-bromo-N,N,4-t...

Learn More

N-(4-Bromophenyl)-3-oxobutanamide Structure

N-(4-Bromopheny...

~%

6-bromo-N,N,4-trimethylquinolin-2-amine Structure

6-bromo-N,N,4-t...

Learn More

6-Bromo-4-methyl-2-quinolinol Structure

6-Bromo-4-methy...

~%

6-bromo-N,N,4-trimethylquinolin-2-amine Structure

6-bromo-N,N,4-t...

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6-Bromo-2-chloro-4-methylquinoline Structure

6-Bromo-2-chlor...

~%

2-(dimethylamino)-4-methylquinoline-6-carbaldehyde Structure

2-(dimethylamin...

Learn More

N-(4-Bromophenyl)-3-oxobutanamide Structure

N-(4-Bromopheny...

~%

2-(dimethylamino)-4-methylquinoline-6-carbaldehyde Structure

2-(dimethylamin...

Learn More

6-Bromo-4-methyl-2-quinolinol Structure

6-Bromo-4-methy...

~%

2-(dimethylamino)-4-methylquinoline-6-carbaldehyde Structure

2-(dimethylamin...

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N,N-Dimethylformamide Structure

N,N-Dimethylfor...

6-bromo-N,N,4-trimethylquinolin-2-amine Structure

6-bromo-N,N,4-t...

~%

2-(dimethylamino)-4-methylquinoline-6-carbaldehyde Structure

2-(dimethylamin...

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4-Bromo-2-methylaniline Structure

4-Bromo-2-methy...

~%

4,8-dimethyl-2-morpholin-4-ylquinoline-6-carbaldehyde Structure

4,8-dimethyl-2-...

Learn More

6-bromo-2-chloro-4,8-dimethylquinoline Structure

6-bromo-2-chlor...

~%

4,8-dimethyl-2-morpholin-4-ylquinoline-6-carbaldehyde Structure

4,8-dimethyl-2-...

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6-bromo-4,8-dimethyl-1H-quinolin-2-one Structure

6-bromo-4,8-dim...

~%

4,8-dimethyl-2-morpholin-4-ylquinoline-6-carbaldehyde Structure

4,8-dimethyl-2-...

Learn More

N-(4-bromo-2-methylphenyl)-3-oxobutanamide Structure

N-(4-bromo-2-me...

~%

4,8-dimethyl-2-morpholin-4-ylquinoline-6-carbaldehyde Structure

4,8-dimethyl-2-...

Learn More

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

4-(6-bromo-4,8-dimethylquinolin-2-yl)morpholine Structure

4-(6-bromo-4,8-...

~%

4,8-dimethyl-2-morpholin-4-ylquinoline-6-carbaldehyde Structure

4,8-dimethyl-2-...

Learn More

6-Bromo-4-methyl-2-quinolinol Structure

6-Bromo-4-methy...

~95%

6-Bromo-2-chloro-4-methylquinoline Structure

6-Bromo-2-chlor...

Learn More

N-(3-bromophenyl)-3-oxo-butanamide Structure

N-(3-bromopheny...

~%

7-Bromo-2-chloro-4-methyl-1-azanaphthalene Structure

7-Bromo-2-chlor...

Learn More

Sodium Methylate Structure

Sodium Methylate

7-Bromo-2-chloro-4-methyl-1-azanaphthalene Structure

7-Bromo-2-chlor...

~85%

7-bromo-2-methoxy-4-methylquinoline Structure

7-bromo-2-metho...

Learn More

N-(3-bromophenyl)-3-oxo-butanamide Structure

N-(3-bromopheny...

~%

7-bromo-2-methoxy-4-methylquinoline Structure

7-bromo-2-metho...

Learn More

7-bromo-4-methyl-1H-quinolin-2-one Structure

7-bromo-4-methy...

~%

7-bromo-2-methoxy-4-methylquinoline Structure

7-bromo-2-metho...

Learn More

4-Bromo-o-anisidine Structure

4-Bromo-o-anisidine

Ethyl acetoacetate Structure

Ethyl acetoacetate

~79%

ethyl 3-(4-bromo-2-methoxyphenyl)iminobutanoate Structure

ethyl 3-(4-brom...

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2-Anisidine Structure

~%

ethyl 3-(4-bromo-2-methoxyphenyl)iminobutanoate Structure

ethyl 3-(4-brom...

Learn More

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

7-bromo-2-methoxy-4-methylquinoline Structure

7-bromo-2-metho...

~%

2-methoxy-4-methylquinoline-7-carbaldehyde Structure

2-methoxy-4-met...

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N-(3-bromophenyl)-3-oxo-butanamide Structure

N-(3-bromopheny...

~%

2-methoxy-4-methylquinoline-7-carbaldehyde Structure

2-methoxy-4-met...

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7-bromo-4-methyl-1H-quinolin-2-one Structure

7-bromo-4-methy...

~%

2-methoxy-4-methylquinoline-7-carbaldehyde Structure

2-methoxy-4-met...

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7-Bromo-2-chloro-4-methyl-1-azanaphthalene Structure

7-Bromo-2-chlor...

~%

2-methoxy-4-methylquinoline-7-carbaldehyde Structure

2-methoxy-4-met...

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Guanidine hydrochloride Structure

Guanidine hydro...

N/A Structure

~13%

5-[(2-methoxy-4-methylquinolin-7-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(2-methoxy-4...

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N-(3-bromophenyl)-3-oxo-butanamide Structure

N-(3-bromopheny...

~%

5-[(2-methoxy-4-methylquinolin-7-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(2-methoxy-4...

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7-bromo-4-methyl-1H-quinolin-2-one Structure

7-bromo-4-methy...

~%

5-[(2-methoxy-4-methylquinolin-7-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(2-methoxy-4...

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7-Bromo-2-chloro-4-methyl-1-azanaphthalene Structure

7-Bromo-2-chlor...

~%

5-[(2-methoxy-4-methylquinolin-7-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(2-methoxy-4...

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7-bromo-2-methoxy-4-methylquinoline Structure

7-bromo-2-metho...

~%

5-[(2-methoxy-4-methylquinolin-7-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(2-methoxy-4...

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2-methoxy-4-methylquinoline-7-carbaldehyde Structure

2-methoxy-4-met...

~%

5-[(2-methoxy-4-methylquinolin-7-yl)methyl]pyrimidine-2,4-diamine Structure

5-[(2-methoxy-4...

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Diketene Structure

4-Bromo-2-methylaniline Structure

4-Bromo-2-methy...

~54%

N-(4-bromo-2-methylphenyl)-3-oxobutanamide Structure

N-(4-bromo-2-me...

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