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

Folate antagonists. 22. Antimalarial and antibacterial effects of 2, 4-diamino-6-quinazolinesulfonamides

…, NL Colbry, J Davoll, MP Hutt, JL Johnson…

Index: Elslager; Colbry; Davoll; Hutt; Johnson; Werbel Journal of Medicinal Chemistry, 1984 , vol. 27, # 12 p. 1740 - 1743

Full Text: HTML

Citation Number: 22

Abstract

The even greater activity uncovered with the development of the 6-arylthio analogues represented by 11, demonstrating the utility of a S spacer coupled with the possibility of introducing a dual inhibitory mechanism; ie, inhibition, of PABA incorporation along with DHFR inhibition encouraged the preparation of a series of 2, 4-di-amino-6- quinazolinesulfonamides 111. The synthesis and biological activity of this series are the ...

2,4,6-triamino-5-chloroquinazoline Structure

2,4,6-triamino-...

~%

2,4-diamino-5-chloro-N,N-diethylquinazoline-6-sulfonamide Structure

2,4-diamino-5-c...

2,4-diamino-5-chloroquinazoline-6-sulfonyl chloride Structure

2,4-diamino-5-c...

Diethylamine Structure

~%

2,4-diamino-5-chloro-N,N-diethylquinazoline-6-sulfonamide Structure

2,4-diamino-5-c...

1,2-Ethanediamine,N1,N1-diethyl-N2-methyl- Structure

1,2-Ethanediami...

N/A Structure

~60%

2,4-diamino-N-[2-(diethylamino)ethyl]-N-methylquinazoline-6-sulfonamide Structure

2,4-diamino-N-[...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

2,4-diamino-N-[2-(diethylamino)ethyl]-N-methylquinazoline-6-sulfonamide Structure

2,4-diamino-N-[...

4-Piperidinopiperidine Structure

4-Piperidinopip...

N/A Structure

~45%

6-(4-piperidin-1-ylpiperidin-1-yl)sulfonylquinazoline-2,4-diamine Structure

6-(4-piperidin-...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

6-(4-piperidin-1-ylpiperidin-1-yl)sulfonylquinazoline-2,4-diamine Structure

6-(4-piperidin-...

N-Carbethoxy Piperazine Structure

N-Carbethoxy Pi...

N/A Structure

~55%

ethyl 4-(2,4-diaminoquinazolin-6-yl)sulfonylpiperazine-1-carboxylate Structure

ethyl 4-(2,4-di...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

ethyl 4-(2,4-diaminoquinazolin-6-yl)sulfonylpiperazine-1-carboxylate Structure

ethyl 4-(2,4-di...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

2,4-diamino-N-(3,4-dichlorophenyl)quinazoline-6-sulfonamide Structure

2,4-diamino-N-(...

N/A Structure

3,4-Dichloroaniline Structure

3,4-Dichloroaniline

~41%

2,4-diamino-N-(3,4-dichlorophenyl)quinazoline-6-sulfonamide Structure

2,4-diamino-N-(...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

6-pyrrolidin-1-ylsulfonylquinazoline-2,4-diamine Structure

6-pyrrolidin-1-...

Pyrrolidine Structure

N/A Structure

~29%

6-pyrrolidin-1-ylsulfonylquinazoline-2,4-diamine Structure

6-pyrrolidin-1-...

3-Chloro-N-methylaniline Structure

3-Chloro-N-meth...

N/A Structure

~44%

2,4-diamino-N-(3-chlorophenyl)-N-methylquinazoline-6-sulfonamide Structure

2,4-diamino-N-(...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

2,4-diamino-N-(3-chlorophenyl)-N-methylquinazoline-6-sulfonamide Structure

2,4-diamino-N-(...

N/A Structure

N-Methylaniline Structure

N-Methylaniline

~60%

2,4-diamino-N-methyl-N-phenylquinazoline-6-sulfonamide Structure

2,4-diamino-N-m...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

6-piperidin-1-ylsulfonylquinazoline-2,4-diamine Structure

6-piperidin-1-y...

Piperidine Structure

N/A Structure

~36%

6-piperidin-1-ylsulfonylquinazoline-2,4-diamine Structure

6-piperidin-1-y...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

2,4-diamino-N-methyl-N-phenylquinazoline-6-sulfonamide Structure

2,4-diamino-N-m...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

2,4-diamino-N-[(3,4-dichlorophenyl)methyl]-N-methylquinazoline-6-sulfonamide Structure

2,4-diamino-N-[...

1-(3,4-Dichlorophenyl)-N-methylmethanamine Structure

1-(3,4-Dichloro...

N/A Structure

~36%

2,4-diamino-N-[(3,4-dichlorophenyl)methyl]-N-methylquinazoline-6-sulfonamide Structure

2,4-diamino-N-[...

N/A Structure

~%

2,4-diaminoquinazoline-6-sulfonamide Structure

2,4-diaminoquin...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

2,4-diaminoquinazoline-6-sulfonamide Structure

2,4-diaminoquin...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

2,4-diamino-N-(3-bromophenyl)quinazoline-6-sulfonamide Structure

2,4-diamino-N-(...

N/A Structure

3-Bromoaniline Structure

~41%

2,4-diamino-N-(3-bromophenyl)quinazoline-6-sulfonamide Structure

2,4-diamino-N-(...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

6-(3,4-dihydro-1H-isoquinolin-2-ylsulfonyl)quinazoline-2,4-diamine Structure

6-(3,4-dihydro-...

1,2,3,4-Tetrahydroisoquinoline Structure

1,2,3,4-Tetrahy...

N/A Structure

~35%

6-(3,4-dihydro-1H-isoquinolin-2-ylsulfonyl)quinazoline-2,4-diamine Structure

6-(3,4-dihydro-...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

2,4-diamino-N,N-dipropylquinazoline-6-sulfonamide Structure

2,4-diamino-N,N...

Dipropylamine Structure

N/A Structure

~%

2,4-diamino-N,N-dipropylquinazoline-6-sulfonamide Structure

2,4-diamino-N,N...

Thiomorpholine Structure

N/A Structure

~65%

6-thiomorpholin-4-ylsulfonylquinazoline-2,4-diamine Structure

6-thiomorpholin...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

6-thiomorpholin-4-ylsulfonylquinazoline-2,4-diamine Structure

6-thiomorpholin...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

6-Quinazolinesulfonamide,2,4-diamino-N,N-diethyl- Structure

6-Quinazolinesu...

N/A Structure

Diethylamine Structure

~%

6-Quinazolinesulfonamide,2,4-diamino-N,N-diethyl- Structure

6-Quinazolinesu...

morpholine Structure

N/A Structure

~59%

6-morpholin-4-ylsulfonylquinazoline-2,4-diamine Structure

6-morpholin-4-y...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

6-morpholin-4-ylsulfonylquinazoline-2,4-diamine Structure

6-morpholin-4-y...

2,4,6-triamino-5-chloroquinazoline Structure

2,4,6-triamino-...

~%

2,4-diamino-5-chloro-N,N-dimethylquinazoline-6-sulfonamide Structure

2,4-diamino-5-c...

quinazoline-2,4-diamine,sulfuric acid Structure

quinazoline-2,4...

~%

6-(4-methylpiperazin-1-yl)sulfonylquinazoline-2,4-diamine Structure

6-(4-methylpipe...

methylpiperazine Structure

methylpiperazine

N/A Structure

~41%

6-(4-methylpiperazin-1-yl)sulfonylquinazoline-2,4-diamine Structure

6-(4-methylpipe...

2,4-diamino-5-chloroquinazoline-6-sulfonyl chloride Structure

2,4-diamino-5-c...

Dimethylamine Structure

~%

2,4-diamino-5-chloro-N,N-dimethylquinazoline-6-sulfonamide Structure

2,4-diamino-5-c...