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

Potential inhibitors of nucleotide biosynthesis. 1. Nitrosoureidonucleosides. 2

…, HJ Thomas, RW Brockman, GP Wheeler

Index: Montgomery, John A.; Thomas, H. Jeanette; Brockman, R. Wallace; Wheeler, Glynn P. Journal of Medicinal Chemistry, 1981 , vol. 24, # 2 p. 184 - 189

Full Text: HTML

Citation Number: 23

Abstract

Several nitrosoureidonucleosides (9a, 9b, lla, llb, 18 and 20) designed as inhibitors of enzymes that metabolize purine and pyrimidine nucleotides have been prepared and their chemical and biological properties studied. The low level of biological activity observed may be due to the unexpected stability of these nitrosoureas compared to biologically active compounds such as N-methyl-N-nitrwurea (MNU), N~-bis (2-chloroethyl)-N'-nitrosourea ( ...

N-(2-aminoethyl)-N-cyclohexylurea Structure

N-(2-aminoethyl...

~%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

cyclohexylisocyanate Structure

cyclohexylisocyanate

~%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

b-D-Ribofuranuronic acid,1-deoxy-1-(1,6-dihydro-6-oxo-9H-purin-9-yl)- Structure

b-D-Ribofuranur...

~%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

N-[2-(cyclohexylcarbamoylamino)ethyl]-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

~22%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

b-D-Ribofuranuronamide,N-[2-[[(cyclohexylamino)carbonyl]amino]ethyl]-1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-Ribofuranur...

~38%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

N-(2-aminoethyl)-N-cyclohexylurea Structure

N-(2-aminoethyl...

~%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

cyclohexylisocyanate Structure

cyclohexylisocyanate

~%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

b-D-Ribofuranuronic acid,1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-Ribofuranur...

~%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

N-(2-aminoethyl)-N-cyclohexylurea Structure

N-(2-aminoethyl...

b-D-Ribofuranuronic acid,1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-Ribofuranur...

~52%

b-D-Ribofuranuronamide,N-[2-[[(cyclohexylamino)carbonyl]amino]ethyl]-1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-Ribofuranur...

cyclohexylisocyanate Structure

cyclohexylisocyanate

~%

b-D-Ribofuranuronamide,N-[2-[[(cyclohexylamino)carbonyl]amino]ethyl]-1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-Ribofuranur...

1,2-Ethanediamine Structure

1,2-Ethanediamine

Methylisocyanate 1 x 500mg neat Structure

Methylisocyanat...

~30%

3-methyl-1-[2-(methylcarbamoylamino)ethyl]urea Structure

3-methyl-1-[2-(...

1-(2-aminoethyl)-3-methylurea Structure

1-(2-aminoethyl...

N-(2-aminoethyl)-N-cyclohexylurea Structure

N-(2-aminoethyl...

b-D-Ribofuranuronic acid,1-deoxy-1-(1,6-dihydro-6-oxo-9H-purin-9-yl)- Structure

b-D-Ribofuranur...

~71%

N-[2-(cyclohexylcarbamoylamino)ethyl]-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

cyclohexylisocyanate Structure

cyclohexylisocyanate

~%

N-[2-(cyclohexylcarbamoylamino)ethyl]-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

N-(2-aminoethyl)-N-cyclohexylurea Structure

N-(2-aminoethyl...

b-D-erythro-Pentofuranuronic acid,1,2-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-erythro-Pen...

~81%

b-D-erythro-Pentofuranuronamide,N-[2-[[(cyclohexylamino)carbonyl]amino]ethyl]-1,2-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-erythro-Pen...

cyclohexylisocyanate Structure

cyclohexylisocyanate

~%

b-D-erythro-Pentofuranuronamide,N-[2-[[(cyclohexylamino)carbonyl]amino]ethyl]-1,2-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-erythro-Pen...

b-D-Ribofuranuronic acid,1-deoxy-1-(1,6-dihydro-6-oxo-9H-purin-9-yl)- Structure

b-D-Ribofuranur...

~%

3,4-dihydroxy-N-[2-[(methyl-nitroso-carbamoyl)amino]ethyl]-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

3,4-dihydroxy-N...

3,4-dihydroxy-N-[2-(methylcarbamoylamino)ethyl]-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

3,4-dihydroxy-N...

~%

(2S,3S,4R,5R)-3,4-dihydroxy-N-(2-(3-methyl-1-nitrosoureido)ethyl)-5-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-2-carboxamide Structure

(2S,3S,4R,5R)-3...

3,4-dihydroxy-N-[2-[(methyl-nitroso-carbamoyl)amino]ethyl]-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

3,4-dihydroxy-N...

3-hydroxy-N-[2-(methylcarbamoylamino)ethyl]-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolane-2-carboxamide Structure

3-hydroxy-N-[2-...

~41%

(2S,3S,5R)-3-hydroxy-5-(2-hydroxy-5-methyl-4-oxopyrimidin-1(4H)-yl)-N-(2-(3-methyl-1-nitrosoureido)ethyl)tetrahydrofuran-2-carboxamide Structure

(2S,3S,5R)-3-hy...

3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-N-[2-[(methyl-nitroso-carbamoyl)amino]ethyl]oxolane-2-carboxamide Structure

3-hydroxy-5-(5-...

b-D-erythro-Pentofuranuronic acid,1,2-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-erythro-Pen...

~%

3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-N-[2-[(methyl-nitroso-carbamoyl)amino]ethyl]oxolane-2-carboxamide Structure

3-hydroxy-5-(5-...

b-D-Ribofuranuronic acid,1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-Ribofuranur...

~%

5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-N-[2-[(methyl-nitroso-carbamoyl)amino]ethyl]oxolane-2-carboxamide Structure

5-(2,4-dioxopyr...

1-(2-aminoethyl)-3-methylurea Structure

1-(2-aminoethyl...

b-D-Ribofuranuronic acid,1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-Ribofuranur...

~44%

b-D-Ribofuranuronamide,1-deoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-N-[2-[[(methylamino)carbonyl]amino]ethyl]- Structure

b-D-Ribofuranur...

b-D-erythro-Pentofuranuronamide,N-[2-[[(cyclohexylamino)carbonyl]amino]ethyl]-1,2-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-erythro-Pen...

~58%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

N-(2-aminoethyl)-N-cyclohexylurea Structure

N-(2-aminoethyl...

~%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

cyclohexylisocyanate Structure

cyclohexylisocyanate

~%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

b-D-erythro-Pentofuranuronic acid,1,2-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-erythro-Pen...

~%

N-[2-(cyclohexylcarbamoyl-nitroso-amino)ethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolane-2-carboxamide Structure

N-[2-(cyclohexy...

b-D-erythro-Pentofuranuronic acid,1,2-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)- Structure

b-D-erythro-Pen...

1-(2-aminoethyl)-3-methylurea Structure

1-(2-aminoethyl...

~74%

3-hydroxy-N-[2-(methylcarbamoylamino)ethyl]-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolane-2-carboxamide Structure

3-hydroxy-N-[2-...

1,2-Ethanediamine Structure

1,2-Ethanediamine

Methylisocyanate 1 x 500mg neat Structure

Methylisocyanat...

~59%

3-methyl-1-[2-(methylcarbamoylamino)ethyl]urea Structure

3-methyl-1-[2-(...

1-(2-aminoethyl)-3-methylurea Structure

1-(2-aminoethyl...

1-(2-aminoethyl)-3-methylurea Structure

1-(2-aminoethyl...

b-D-Ribofuranuronic acid,1-deoxy-1-(1,6-dihydro-6-oxo-9H-purin-9-yl)- Structure

b-D-Ribofuranur...

~79%

3,4-dihydroxy-N-[2-(methylcarbamoylamino)ethyl]-5-(6-oxo-3H-purin-9-yl)oxolane-2-carboxamide Structure

3,4-dihydroxy-N...