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 ( ...

 Related Synthetic Route
N-(2-aminoethyl)-N-cyclohexylurea Structure

75930-39-1

N-(2-aminoethyl...

~%

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

75930-25-5

N-[2-(cyclohexy...

Learn More
cyclohexylisocyanate Structure

3173-53-3

cyclohexylisocyanate

~%

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

75930-25-5

N-[2-(cyclohexy...

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

15475-13-5

b-D-Ribofuranur...

~%

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

75930-25-5

N-[2-(cyclohexy...

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

75930-32-4

N-[2-(cyclohexy...

~22%

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

75930-25-5

N-[2-(cyclohexy...

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

75930-33-5

b-D-Ribofuranur...

~38%

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

75930-26-6

N-[2-(cyclohexy...

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

75930-39-1

N-(2-aminoethyl...

~%

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

75930-26-6

N-[2-(cyclohexy...

Learn More
cyclohexylisocyanate Structure

3173-53-3

cyclohexylisocyanate

~%

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

75930-26-6

N-[2-(cyclohexy...

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

3415-07-4

b-D-Ribofuranur...

~%

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

75930-26-6

N-[2-(cyclohexy...

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

75930-39-1

N-(2-aminoethyl...

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

3415-07-4

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

75930-33-5

b-D-Ribofuranur...

Learn More
cyclohexylisocyanate Structure

3173-53-3

cyclohexylisocyanate

~%

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

75930-33-5

b-D-Ribofuranur...

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1,2-Ethanediamine Structure

107-15-3

1,2-Ethanediamine

Methylisocyanate 1 x 500mg neat Structure

624-83-9

Methylisocyanat...

~30%

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

62183-21-5

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

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

75930-29-9

1-(2-aminoethyl...

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

75930-39-1

N-(2-aminoethyl...

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

15475-13-5

b-D-Ribofuranur...

~71%

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

75930-32-4

N-[2-(cyclohexy...

Learn More
cyclohexylisocyanate Structure

3173-53-3

cyclohexylisocyanate

~%

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

75930-32-4

N-[2-(cyclohexy...

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

75930-39-1

N-(2-aminoethyl...

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

3544-99-8

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

75930-35-7

b-D-erythro-Pen...

Learn More
cyclohexylisocyanate Structure

3173-53-3

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

75930-35-7

b-D-erythro-Pen...

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

15475-13-5

b-D-Ribofuranur...

~%

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

75930-23-3

3,4-dihydroxy-N...

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

75930-30-2

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

75930-37-9

(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

75930-23-3

3,4-dihydroxy-N...

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

75930-34-6

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

75930-36-8

(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

75930-27-7

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

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

3544-99-8

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

75930-27-7

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

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

3415-07-4

b-D-Ribofuranur...

~%

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

75930-24-4

5-(2,4-dioxopyr...

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

75930-29-9

1-(2-aminoethyl...

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

3415-07-4

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

75930-31-3

b-D-Ribofuranur...

Learn More
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

75930-35-7

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

75930-28-8

N-[2-(cyclohexy...

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

75930-39-1

N-(2-aminoethyl...

~%

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

75930-28-8

N-[2-(cyclohexy...

Learn More
cyclohexylisocyanate Structure

3173-53-3

cyclohexylisocyanate

~%

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

75930-28-8

N-[2-(cyclohexy...

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

3544-99-8

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

75930-28-8

N-[2-(cyclohexy...

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

3544-99-8

b-D-erythro-Pen...

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

75930-29-9

1-(2-aminoethyl...

~74%

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

75930-34-6

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

Learn More
1,2-Ethanediamine Structure

107-15-3

1,2-Ethanediamine

Methylisocyanate 1 x 500mg neat Structure

624-83-9

Methylisocyanat...

~59%

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

62183-21-5

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

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

75930-29-9

1-(2-aminoethyl...

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

75930-29-9

1-(2-aminoethyl...

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

15475-13-5

b-D-Ribofuranur...

~79%

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

75930-30-2

3,4-dihydroxy-N...

Learn More

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