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

Activated N-nitrosocarbamates for regioselective synthesis of N-nitrosoureas

…, J Oiry, JL Imbach, F Winternitz

Index: Martinez, Jean; Oiry, Joel; Imbach, Jean Louis; Winternitz, Francois Journal of Medicinal Chemistry, 1982 , vol. 25, # 2 p. 178 - 182

Full Text: HTML

Citation Number: 63

Abstract

A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N- nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed. N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N- nitrosoureas. As an interesting example, N, N'-bis [(2-chloroethyl) nitrosocarbamoyl] ...

Methylisocyanate 1 x 500mg neat Structure

Methylisocyanat...

2,4,5-Trichlorophenol Structure

2,4,5-Trichloro...

~85%

Phenol,2,4,5-trichloro-, 1-(N-methylcarbamate) Structure

Phenol,2,4,5-tr...

Carbamic acid, (2-chloroethyl)-, 2,4,5-trichlorophenyl ester Structure

Carbamic acid, ...

~94%

(2,4,5-trichlorophenyl) N-(2-chloroethyl)-N-nitroso-carbamate Structure

(2,4,5-trichlor...

1-Chloro-2-isocyanatoethane Structure

1-Chloro-2-isoc...

2,4,5-Trichlorophenol Structure

2,4,5-Trichloro...

~81%

Carbamic acid, (2-chloroethyl)-, 2,4,5-trichlorophenyl ester Structure

Carbamic acid, ...

1-[(Methylcarbamoyl)oxy]-2,5-pyrrolidinedione Structure

1-[(Methylcarba...

~98%

(2,5-dioxopyrrolidin-1-yl) N-methyl-N-nitrosocarbamate Structure

(2,5-dioxopyrro...

N-Hydroxysuccinimide Structure

N-Hydroxysuccinimide

Methylisocyanate 1 x 500mg neat Structure

Methylisocyanat...

~80%

1-[(Methylcarbamoyl)oxy]-2,5-pyrrolidinedione Structure

1-[(Methylcarba...

(2,4,5-trichlorophenyl) N-(2-chloroethyl)-N-nitroso-carbamate Structure

(2,4,5-trichlor...

Cystamine dihydrochloride Structure

Cystamine dihyd...

~73%

1-(2-chloroethyl)-3-[2-[2-[(2-chloroethyl-nitroso-carbamoyl)amino]ethy ldisulfanyl]ethyl]-1-nitroso-urea Structure

1-(2-chloroethy...

Cystamine dihydrochloride Structure

Cystamine dihyd...

(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

(2,3,4,5,6-pent...

~75%

1-(2-chloroethyl)-3-[2-[2-[(2-chloroethyl-nitroso-carbamoyl)amino]ethy ldisulfanyl]ethyl]-1-nitroso-urea Structure

1-(2-chloroethy...

Cystamine dihydrochloride Structure

Cystamine dihyd...

CARBAMIC ACID, (2-CHLOROETHYL)NITROSO-, 2,5-DIOXO-1-PYRROLIDINYL ESTER Structure

CARBAMIC ACID, ...

~75%

1-(2-chloroethyl)-3-[2-[2-[(2-chloroethyl-nitroso-carbamoyl)amino]ethy ldisulfanyl]ethyl]-1-nitroso-urea Structure

1-(2-chloroethy...

Cystamine dihydrochloride Structure

Cystamine dihyd...

pentafluorophenyl N-(2-chloroethyl)-N-nitrosocarbamate Structure

pentafluorophen...

~76%

1-(2-chloroethyl)-3-[2-[2-[(2-chloroethyl-nitroso-carbamoyl)amino]ethy ldisulfanyl]ethyl]-1-nitroso-urea Structure

1-(2-chloroethy...

(2,5-dioxopyrrolidin-1-yl) N-(2-chloroethyl)carbamate Structure

(2,5-dioxopyrro...

~93%

CARBAMIC ACID, (2-CHLOROETHYL)NITROSO-, 2,5-DIOXO-1-PYRROLIDINYL ESTER Structure

CARBAMIC ACID, ...

N/A Structure

~94%

(2,3,4,5,6-pentachlorophenyl) N-methyl-N-nitrosocarbamate Structure

(2,3,4,5,6-pent...

Peratox Structure

~%

(2,3,4,5,6-pentachlorophenyl) N-methyl-N-nitrosocarbamate Structure

(2,3,4,5,6-pent...

pentachlorophenyl N-(2-chloroethyl)carbamate Structure

pentachlorophen...

~%

(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

(2,3,4,5,6-pent...

Peratox Structure

~%

(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

(2,3,4,5,6-pent...

(2,4,5-trichlorophenyl) N-(2-chloroethyl)-N-nitroso-carbamate Structure

(2,4,5-trichlor...

Cyclohexylamine Structure

Cyclohexylamine

~79%

Lomustine Structure

(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

(2,3,4,5,6-pent...

Cyclohexylamine Structure

Cyclohexylamine

~82%

Lomustine Structure

Cyclohexylamine Structure

Cyclohexylamine

pentafluorophenyl N-(2-chloroethyl)-N-nitrosocarbamate Structure

pentafluorophen...

~81%

Lomustine Structure

(3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Structure

(3R,4R,5R,6R)-3...

(2,4,5-trichlorophenyl) N-(2-chloroethyl)-N-nitroso-carbamate Structure

(2,4,5-trichlor...

~80%

2-((3-chloroethyl)-3-nitrosoureido)glucopyranose Structure

2-((3-chloroeth...

(3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Structure

(3R,4R,5R,6R)-3...

(2,3,4,5,6-pentachlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate Structure

(2,3,4,5,6-pent...

~81%

2-((3-chloroethyl)-3-nitrosoureido)glucopyranose Structure

2-((3-chloroeth...

(3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Structure

(3R,4R,5R,6R)-3...

CARBAMIC ACID, (2-CHLOROETHYL)NITROSO-, 2,5-DIOXO-1-PYRROLIDINYL ESTER Structure

CARBAMIC ACID, ...

~80%

2-((3-chloroethyl)-3-nitrosoureido)glucopyranose Structure

2-((3-chloroeth...

(3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Structure

(3R,4R,5R,6R)-3...

pentafluorophenyl N-(2-chloroethyl)-N-nitrosocarbamate Structure

pentafluorophen...

~81%

2-((3-chloroethyl)-3-nitrosoureido)glucopyranose Structure

2-((3-chloroeth...

A convenient method for the synthesis of activated N-methylc...

[Konakahara; Ozaki; Sato; Gold Synthesis, 1993 , # 1 p. 103 - 106]

A convenient method for the synthesis of activated N-methylc...

[Konakahara; Ozaki; Sato; Gold Synthesis, 1993 , # 1 p. 103 - 106]