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

1, 2-Dihydropyrido [3, 4-b] pyrazines: structure-activity relationships

…, JD Rose, RN Comber, JA Montgomery

Index: Temple Jr.; Wheeler; Elliott; Rose; Comber; Montgomery Journal of Medicinal Chemistry, 1983 , vol. 26, # 1 p. 91 - 95

Full Text: HTML

Citation Number: 19

Abstract

Certain derivatives containing the 1, 2-dihydropyrido [3, 4-blpyrazine (l-deaza-7, 8- dihydropteridine) ring system are active against experimental neoplasms in mice. The mechanism of action of these agents has been attributed to the accumulation of cells at mitosis. Identification of the structural features that are necessary for activity was accomplished by evaluation of modified 1-deazapteridines and ring and ring-opened ...

ethyl N-[5-amino-3-[(N-methylanilino)methyl]-1,2-dihydropyrido[3,4-b]pyrazin-7-yl]carbamate Structure

ethyl N-[5-amin...

~12%

ethyl N-[2-amino-9-[(methyl-phenyl-amino)methyl]-3,7,10-triazabicyclo[4.4.0]deca-1,3,5,7,9-pentaen-4-yl]carbamate Structure

ethyl N-[2-amin...

Carbamic acid, [5-amino-3-[(methylphenylamino)carbonyl]pyrido[3,4-b]pyrazin-7-yl]-, ethyl ester (9CI) Structure

Carbamic acid, ...

Ethyl 3-oxo-3-phenylpropanoate Structure

Ethyl 3-oxo-3-p...

ethyl (5,6-diaminopyridin-2-yl)carbamate Structure

ethyl (5,6-diam...

~%

ethyl (E)-3-[[2-amino-6-(ethoxycarbonylamino)pyridin-3-yl]amino]-3-phenyl-prop-2-enoate Structure

ethyl (E)-3-[[2...

ethyl N-[6-amino-4-[(2-naphthalen-2-yl-2-oxo-ethyl)amino]-5-nitro-pyridin-2-yl]carbamate Structure

ethyl N-[6-amin...

~%

Carbamic acid, (5-amino-1,2-dihydro-3-(2-naphthalenyl)pyrido(3,4-b)pyr azin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

(NE)-N-(2-amino-1-naphthalen-2-yl-ethylidene)hydroxylamine Structure

(NE)-N-(2-amino...

~%

Carbamic acid, (5-amino-1,2-dihydro-3-(2-naphthalenyl)pyrido(3,4-b)pyr azin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

ethyl N-[6-amino-4-[[(2E)-2-hydroxyimino-2-naphthalen-2-yl-ethyl]amino]-5-nitro-pyridin-2-yl]carbamate Structure

ethyl N-[6-amin...

~%

Carbamic acid, (5-amino-1,2-dihydro-3-(2-naphthalenyl)pyrido(3,4-b)pyr azin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

ethyl 6-amino-4-[(1-methyl-2-oxo-2-phenylethyl)amino]-5-nitro-2-pyridinecarbamate Structure

ethyl 6-amino-4...

~71%

ethyl N-(5-amino-9-methyl-8-phenyl-4,7,10-triazabicyclo[4.4.0]deca-1,3 ,5,7-tetraen-3-yl)carbamate Structure

ethyl N-(5-amin...

α-aminopropiophenone oxime Structure

α-aminopropioph...

~%

ethyl N-(5-amino-9-methyl-8-phenyl-4,7,10-triazabicyclo[4.4.0]deca-1,3 ,5,7-tetraen-3-yl)carbamate Structure

ethyl N-(5-amin...

Carbamic acid, (6-amino-4-(2-(3-(hydroxyimino)-3-phenyl)propyl)amino)-5-nitro-2-pyridinyl-, ethyl ester Structure

Carbamic acid, ...

~%

ethyl N-(5-amino-9-methyl-8-phenyl-4,7,10-triazabicyclo[4.4.0]deca-1,3 ,5,7-tetraen-3-yl)carbamate Structure

ethyl N-(5-amin...

Carbamic acid, (5-amino-1,2-dihydro-3-(4-(trifluoromethyl)phenyl)pyrid o(3,4-b)pyrazin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

~19%

ethyl N-[2-amino-9-[4-(trifluoromethyl)phenyl]-3,7,10-triazabicyclo[4.4.0]deca-1,3,5,7,9-pentaen-4-yl]carbamate Structure

ethyl N-[2-amin...

ethyl N-[6-amino-4-[[(2E)-2-hydroxyimino-2-naphthalen-2-yl-ethyl]amino]-5-nitro-pyridin-2-yl]carbamate Structure

ethyl N-[6-amin...

~67%

ethyl N-[6-amino-4-[(2-naphthalen-2-yl-2-oxo-ethyl)amino]-5-nitro-pyridin-2-yl]carbamate Structure

ethyl N-[6-amin...

(NE)-N-(2-amino-1-naphthalen-2-yl-ethylidene)hydroxylamine Structure

(NE)-N-(2-amino...

~%

ethyl N-[6-amino-4-[(2-naphthalen-2-yl-2-oxo-ethyl)amino]-5-nitro-pyridin-2-yl]carbamate Structure

ethyl N-[6-amin...

ethyl 5-nitropyridyl-2-carbamate Structure

ethyl 5-nitropy...

~%

ethyl N-[5-(benzylideneamino)pyridin-2-yl]carbamate Structure

ethyl N-[5-(ben...

Benzaldehyde Structure

ethyl (5-aminopyridin-2-yl)carbamate Structure

ethyl (5-aminop...

~%

ethyl N-[5-(benzylideneamino)pyridin-2-yl]carbamate Structure

ethyl N-[5-(ben...

Carbamic acid, (5-amino-1,2-dihydro-3-phenylpyrido[3, 4-b]pyrazin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

~96%

Carbamic acid,(5-amino-3-phenylpyrido[3,4-b]pyrazin-7-yl)-, ethyl ester (9CI) Structure

Carbamic acid,(...

diethyl 4-((3-(N-methyl-N-phenylamino)-2-oxopropyl)amino)-3-nitro-2,6-pyridinedicarbamate Structure

diethyl 4-((3-(...

~41%

Carbamic acid,[1,2-dihydro-3-[(methylphenylamino)methyl]pyrido[3,4-b]pyrazine-5,7-diyl]bis-,diethyl ester (9CI) Structure

Carbamic acid,[...

ethyl 6-amino-4-[N-methyl-N-(2-oxo-2-phenylethyl)amino]-5-nitro-2-pyridinecarbamate Structure

ethyl 6-amino-4...

~38%

Carbamic acid, (5-amino-1,2-dihydro-1-methyl-3-phenylpyrido(3,4-b)pyrazin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

DL-ALPHA-(METHYLAMINOMETHYL)BENZYL ALCOHOL Structure

DL-ALPHA-(METHY...

~%

Carbamic acid, (5-amino-1,2-dihydro-1-methyl-3-phenylpyrido(3,4-b)pyrazin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

ethyl 6-amino-4-[N-(2-hydroxy-2-phenylethyl)-N-methylamino]-5-nitro-2-pyridinecarbamate Structure

ethyl 6-amino-4...

~%

Carbamic acid, (5-amino-1,2-dihydro-1-methyl-3-phenylpyrido(3,4-b)pyrazin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

Carbamic acid,[6-amino-5-nitro-4-[(2-oxo-4-phenylbutyl)amino]-2-pyridinyl]-, ethyl ester(9CI) Structure

Carbamic acid,[...

~89%

Carbamic acid, (5-amino-1,2-dihydro-3-(2-phenylethyl)pyrido(3,4-b)pyrazin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

Carbamic acid, [6-amino-4-[[2-(hydroxyimino)-4-phenylbutyl]amino]-5-nitro-2-pyridinyl]-,ethyl ester (9CI) Structure

Carbamic acid, ...

~%

Carbamic acid, (5-amino-1,2-dihydro-3-(2-phenylethyl)pyrido(3,4-b)pyrazin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

1-amino-4-phenyl-2-butanone oxime Structure

1-amino-4-pheny...

~%

Carbamic acid, (5-amino-1,2-dihydro-3-(2-phenylethyl)pyrido(3,4-b)pyrazin-7-yl)-, ethyl ester Structure

Carbamic acid, ...

ethyl N-[5-amino-3-[(N-methylanilino)methyl]-1,2-dihydropyrido[3,4-b]pyrazin-7-yl]carbamate Structure

ethyl N-[5-amin...

~18%

ethyl N-[2-amino-9-[(methyl-phenyl-amino)methyl]-3,7,10-triazabicyclo[4.4.0]deca-1,3,5,7,9-pentaen-4-yl]carbamate Structure

ethyl N-[2-amin...

Carbamic acid, [5-amino-3-[(methylphenylamino)carbonyl]pyrido[3,4-b]pyrazin-7-yl]-, ethyl ester (9CI) Structure

Carbamic acid, ...

ethyl N-[5-amino-3-[(N-methylanilino)methyl]-1,2-dihydropyrido[3,4-b]pyrazin-7-yl]carbamate Structure

ethyl N-[5-amin...

~89%

Carbamic acid, [5-amino-1,2,3, 4-tetrahydro-3-[(methylphenylamino)methyl]pyrido[3, 4-b]pyrazin-7-yl]-, ethyl ester Structure

Carbamic acid, ...

Carbamic acid, [6-amino-4-[[2-(hydroxyimino)-4-phenylbutyl]amino]-5-nitro-2-pyridinyl]-,ethyl ester (9CI) Structure

Carbamic acid, ...

~82%

Carbamic acid,[6-amino-5-nitro-4-[(2-oxo-4-phenylbutyl)amino]-2-pyridinyl]-, ethyl ester(9CI) Structure

Carbamic acid,[...

1-amino-4-phenyl-2-butanone oxime Structure

1-amino-4-pheny...

~%

Carbamic acid,[6-amino-5-nitro-4-[(2-oxo-4-phenylbutyl)amino]-2-pyridinyl]-, ethyl ester(9CI) Structure

Carbamic acid,[...