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

Synthesis and antimalarial effects of N2-aryl-N4-[(dialkylamino) alkyl]-and N4-aryl-N2-[(dialkylamino) alkyl]-2, 4-quinazolinediamines

EF Elslager, C Hess, J Johnson, D Ortwine…

Index: Elslager; Hess; Johnson; Ortwine; Chu; Werbel Journal of Medicinal Chemistry, 1981 , vol. 24, # 2 p. 127 - 140

Full Text: HTML

Citation Number: 25

Abstract

Chemistry. The synthetic approach utilized for the preparation of the N44 (dialky1amino) alkyll-W-phenyl-2, 4-quinazolinediamines (VI) involved modifications of previous5p6 procedures and is depicted in Scheme I. Condensation of the appropriate 2, 4- dichloroquinazoline (IV) with the requisite N, N-dialkylalkylenediamine in ether, alcohol- ether, alcohol, nitrobenzene, or dilute aqueous sodium hydroxide5 generated the ...

N/A Structure

3,4-Dichloroaniline Structure

3,4-Dichloroaniline

~51%

6-Chloro-N2-(3,4-dichlorophenyl)-N4-(2-(1-methyl-2-pyrrolidinyl)ethyl)-2,4-quinazolinediamine Structure

6-Chloro-N2-(3,...

2,4,6-Trichloroquinazoline Structure

2,4,6-Trichloro...

~%

6-Chloro-N2-(3,4-dichlorophenyl)-N4-(2-(1-methyl-2-pyrrolidinyl)ethyl)-2,4-quinazolinediamine Structure

6-Chloro-N2-(3,...

N-Methyl-2-(2-aminoethyl)pyrrolidine Structure

N-Methyl-2-(2-a...

~%

6-Chloro-N2-(3,4-dichlorophenyl)-N4-(2-(1-methyl-2-pyrrolidinyl)ethyl)-2,4-quinazolinediamine Structure

6-Chloro-N2-(3,...

2,6-dichloro-N-(1-ethylpiperidin-3-yl)quinazolin-4-amine hydrochloride Structure

2,6-dichloro-N-...

3,5-Dichloroaniline Structure

3,5-Dichloroaniline

~52%

6-chloro-N-(3,5-dichlorophenyl)-N-(1-ethyl-3-piperidyl)quinazoline-2,4-diamine Structure

6-chloro-N-(3,5...

1-ETHYLPIPERIDIN-3-AMINE Structure

1-ETHYLPIPERIDI...

~%

6-chloro-N-(3,5-dichlorophenyl)-N-(1-ethyl-3-piperidyl)quinazoline-2,4-diamine Structure

6-chloro-N-(3,5...

2,4,6-Trichloroquinazoline Structure

2,4,6-Trichloro...

~%

6-chloro-N-(3,5-dichlorophenyl)-N-(1-ethyl-3-piperidyl)quinazoline-2,4-diamine Structure

6-chloro-N-(3,5...

2,6-dichloro-N-(1-ethylpiperidin-3-yl)quinazolin-4-amine hydrochloride Structure

2,6-dichloro-N-...

3,4-Dichloroaniline Structure

3,4-Dichloroaniline

~36%

6-chloro-N-(3,4-dichlorophenyl)-N-(1-ethyl-3-piperidyl)quinazoline-2,4-diamine Structure

6-chloro-N-(3,4...

1-ETHYLPIPERIDIN-3-AMINE Structure

1-ETHYLPIPERIDI...

~%

6-chloro-N-(3,4-dichlorophenyl)-N-(1-ethyl-3-piperidyl)quinazoline-2,4-diamine Structure

6-chloro-N-(3,4...

2,4,6-Trichloroquinazoline Structure

2,4,6-Trichloro...

~%

6-chloro-N-(3,4-dichlorophenyl)-N-(1-ethyl-3-piperidyl)quinazoline-2,4-diamine Structure

6-chloro-N-(3,4...

5-amino-N,N-diethyl-2-methoxybenzenemethanamine Structure

5-amino-N,N-die...

N1-(2-chloroquinazolin-4-yl)-N4,N4-dimethylcyclohexane-1,4-diamine hydrochloride Structure

N1-(2-chloroqui...

~46%

N-[3-(diethylaminomethyl)-4-methoxy-phenyl]-N-(4-dimethylaminocyclohexyl)quinazoline-2,4-diamine Structure

N-[3-(diethylam...

2,4-Dichloroquinazoline Structure

2,4-Dichloroqui...

~%

N-[3-(diethylaminomethyl)-4-methoxy-phenyl]-N-(4-dimethylaminocyclohexyl)quinazoline-2,4-diamine Structure

N-[3-(diethylam...

N,N-Dimethyl-1,4-cyclohexanediamine Structure

N,N-Dimethyl-1,...

~%

N-[3-(diethylaminomethyl)-4-methoxy-phenyl]-N-(4-dimethylaminocyclohexyl)quinazoline-2,4-diamine Structure

N-[3-(diethylam...

2,7-dichloro-N-(1-ethylpiperidin-3-yl)quinazolin-4-amine hydrochloride Structure

2,7-dichloro-N-...

3,5-Dichloroaniline Structure

3,5-Dichloroaniline

~72%

7-chloro-N-(3,5-dichlorophenyl)-N-(1-ethyl-3-piperidyl)quinazoline-2,4-diamine Structure

7-chloro-N-(3,5...

1-ETHYLPIPERIDIN-3-AMINE Structure

1-ETHYLPIPERIDI...

~%

7-chloro-N-(3,5-dichlorophenyl)-N-(1-ethyl-3-piperidyl)quinazoline-2,4-diamine Structure

7-chloro-N-(3,5...

2,4,7-Trichloroquinazoline Structure

2,4,7-Trichloro...

~%

7-chloro-N-(3,5-dichlorophenyl)-N-(1-ethyl-3-piperidyl)quinazoline-2,4-diamine Structure

7-chloro-N-(3,5...