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

Synthesis and sugar reducing activity of dioxamoyl derivatives of sulfanilamide

…, VP Chernykh, PA Petyunin, AV Chuvurin…

Index: Bannyi, I. P.; Chernykh, V. P.; Petyunin, P. A.; Chuvurin, A. V.; Chaleeva, L. D.; et al. Pharmaceutical Chemistry Journal, 1982 , vol. 16, # 1 p. 33 - 37 Khimiko-Farmatsevticheskii Zhurnal, 1982 , vol. 16, # 1 p. 43 - 47

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Abstract

Esters II and amides III were obtained by methods described in [6]. In the reaction of amides III with monoethyl oxalate monoacid chloride (ethoxalyl chloride), NR-amides of 4- (ethoxalylamino) benzenesulfonyloxamic acid (IV, Table i) are formed in yields of 72-86%. The latter with primary alkylamines form NR-amides of 4-(N-R'-oxamido) benzenesulfonyloxamic acid (V, Table 2) in yields of 67-90%. Compounds IV and V are ...

Acetic acid, oxo((4-(((oxo((phenylmethyl)amino)acetyl)amino)sulfonyl)p henyl)amino)-, ethyl ester Structure

Acetic acid, ox...

~77%

N-benzyl-N'-[4-[[2-(hydroxyamino)-2-oxoacetyl]amino]phenyl]sulfonyloxamide Structure

N-benzyl-N'-[4-...

N1-((4-aminophenyl)sulfonyl)-N2-benzyloxalamide Structure

N1-((4-aminophe...

~%

N-benzyl-N'-[4-[[2-(hydroxyamino)-2-oxoacetyl]amino]phenyl]sulfonyloxamide Structure

N-benzyl-N'-[4-...

p-(N-Ethoxalylamino)benzenesulfonyloxamic acid ethyl ester Structure

p-(N-Ethoxalyla...

Benzylamine Structure

~68%

N-benzyl-N'-[4-[[2-(benzylamino)-2-oxoacetyl]sulfamoyl]phenyl]oxamide Structure

N-benzyl-N'-[4-...

Acetic acid, oxo((4-(((oxo((phenylmethyl)amino)acetyl)amino)sulfonyl)p henyl)amino)-, ethyl ester Structure

Acetic acid, ox...

Benzylamine Structure

~66%

N-benzyl-N'-[4-[[2-(benzylamino)-2-oxoacetyl]sulfamoyl]phenyl]oxamide Structure

N-benzyl-N'-[4-...

N-(4-Amino-benzolsulfonyl)-oxamidsaeure-ethylester Structure

N-(4-Amino-benz...

~%

N-benzyl-N'-[4-[[2-(benzylamino)-2-oxoacetyl]sulfamoyl]phenyl]oxamide Structure

N-benzyl-N'-[4-...

ethyl 2-[4-[[2-(2-methylpropylamino)-2-oxoacetyl]sulfamoyl]anilino]-2-oxoacetate Structure

ethyl 2-[4-[[2-...

~81%

N'-[4-[[2-(hydroxyamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N'-(2-methylpropyl)oxamide Structure

N'-[4-[[2-(hydr...

N1-((4-aminophenyl)sulfonyl)-N2-isobutyloxalamide Structure

N1-((4-aminophe...

~%

N'-[4-[[2-(hydroxyamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N'-(2-methylpropyl)oxamide Structure

N'-[4-[[2-(hydr...

ethyl [4-[(2-hydroxyethylcarbamoylformyl)sulfamoyl]phenyl]carbamoylfor mate Structure

ethyl [4-[(2-hy...

methylamine Structure

~76%

N'-[4-[[2-(2-hydroxyethylamino)-2-oxoacetyl]sulfamoyl]phenyl]-N-methyloxamide Structure

N'-[4-[[2-(2-hy...

N1-((4-aminophenyl)sulfonyl)-N2-(2-hydroxyethyl)oxalamide Structure

N1-((4-aminophe...

~%

N'-[4-[[2-(2-hydroxyethylamino)-2-oxoacetyl]sulfamoyl]phenyl]-N-methyloxamide Structure

N'-[4-[[2-(2-hy...

((4-(((Aminoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic acid ethyl es ter Structure

((4-(((Aminoace...

~79%

N-[4-[(hydroxycarbamoylformyl)amino]phenyl]sulfonyloxamide Structure

N-[4-[(hydroxyc...

sulfanilyl-oxalamide Structure

sulfanilyl-oxalamide

~%

N-[4-[(hydroxycarbamoylformyl)amino]phenyl]sulfonyloxamide Structure

N-[4-[(hydroxyc...

Isobutylamine Structure

ethyl [4-[(2-hydroxyethylcarbamoylformyl)sulfamoyl]phenyl]carbamoylfor mate Structure

ethyl [4-[(2-hy...

~79%

N-(2-hydroxyethyl)-N'-[4-[[2-(2-methylpropylamino)-2-oxoacetyl]amino]phenyl]sulfonyloxamide Structure

N-(2-hydroxyeth...

N1-((4-aminophenyl)sulfonyl)-N2-(2-hydroxyethyl)oxalamide Structure

N1-((4-aminophe...

~%

N-(2-hydroxyethyl)-N'-[4-[[2-(2-methylpropylamino)-2-oxoacetyl]amino]phenyl]sulfonyloxamide Structure

N-(2-hydroxyeth...

((4-((((Methylamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic ac id ethyl ester Structure

((4-((((Methyla...

~79%

N'-[4-[methyl(oxamoyl)sulfamoyl]phenyl]oxamide Structure

N'-[4-[methyl(o...

4-Amino-N-benzolsulfonyl-oxamidsaeure-N'-methylamid Structure

4-Amino-N-benzo...

~%

N'-[4-[methyl(oxamoyl)sulfamoyl]phenyl]oxamide Structure

N'-[4-[methyl(o...

Ethoxalyl chloride Structure

Ethoxalyl chloride

N1-((4-aminophenyl)sulfonyl)-N2-benzyloxalamide Structure

N1-((4-aminophe...

~83%

Acetic acid, oxo((4-(((oxo((phenylmethyl)amino)acetyl)amino)sulfonyl)p henyl)amino)-, ethyl ester Structure

Acetic acid, ox...

Propylamine Structure

((4-((((Methylamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic ac id ethyl ester Structure

((4-((((Methyla...

~80%

N'-methyl-N'-[4-[[2-oxo-2-(propylamino)acetyl]amino]phenyl]sulfonyloxamide Structure

N'-methyl-N'-[4...

4-Amino-N-benzolsulfonyl-oxamidsaeure-N'-methylamid Structure

4-Amino-N-benzo...

~%

N'-methyl-N'-[4-[[2-oxo-2-(propylamino)acetyl]amino]phenyl]sulfonyloxamide Structure

N'-methyl-N'-[4...

Isobutylamine Structure

((4-((((Methylamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic ac id ethyl ester Structure

((4-((((Methyla...

~83%

N'-[4-[[2-(methylamino)-2-oxoacetyl]sulfamoyl]phenyl]-N'-(2-methylpropyl)oxamide Structure

N'-[4-[[2-(meth...

4-Amino-N-benzolsulfonyl-oxamidsaeure-N'-methylamid Structure

4-Amino-N-benzo...

~%

N'-[4-[[2-(methylamino)-2-oxoacetyl]sulfamoyl]phenyl]-N'-(2-methylpropyl)oxamide Structure

N'-[4-[[2-(meth...

4-Amino-N-benzolsulfonyl-oxamidsaeure-N'-butylamid Structure

4-Amino-N-benzo...

Ethoxalyl chloride Structure

Ethoxalyl chloride

~81%

Acetic acid, ((4-((((butylamino)oxoacetyl)amino)sulfonyl)phenyl)amino) oxo-, ethyl ester Structure

Acetic acid, ((...

2-Aminoethanol Structure

((4-((((Methylamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic ac id ethyl ester Structure

((4-((((Methyla...

~87%

N'-[4-[[2-(2-hydroxyethylamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N'-methyloxamide Structure

N'-[4-[[2-(2-hy...

4-Amino-N-benzolsulfonyl-oxamidsaeure-N'-methylamid Structure

4-Amino-N-benzo...

~%

N'-[4-[[2-(2-hydroxyethylamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N'-methyloxamide Structure

N'-[4-[[2-(2-hy...

Cyclohexylamine Structure

Cyclohexylamine

((4-((((Methylamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic ac id ethyl ester Structure

((4-((((Methyla...

~83%

N'-[4-[[2-(cyclohexylamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N-methyloxamide Structure

N'-[4-[[2-(cycl...

4-Amino-N-benzolsulfonyl-oxamidsaeure-N'-methylamid Structure

4-Amino-N-benzo...

~%

N'-[4-[[2-(cyclohexylamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N-methyloxamide Structure

N'-[4-[[2-(cycl...

Ethoxalyl chloride Structure

Ethoxalyl chloride

N1-((4-aminophenyl)sulfonyl)-N2-(2-hydroxyethyl)oxalamide Structure

N1-((4-aminophe...

~78%

ethyl [4-[(2-hydroxyethylcarbamoylformyl)sulfamoyl]phenyl]carbamoylfor mate Structure

ethyl [4-[(2-hy...

decanamine Structure

((4-((((Methylamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic ac id ethyl ester Structure

((4-((((Methyla...

~72%

N'-[4-[[2-(decylamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N'-methyloxamide Structure

N'-[4-[[2-(decy...

4-Amino-N-benzolsulfonyl-oxamidsaeure-N'-methylamid Structure

4-Amino-N-benzo...

~%

N'-[4-[[2-(decylamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N'-methyloxamide Structure

N'-[4-[[2-(decy...

N1-((4-aminophenyl)sulfonyl)-N2-hydroxyoxalamide Structure

N1-((4-aminophe...

Ethoxalyl chloride Structure

Ethoxalyl chloride

~73%

((4-((((Hydroxyamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic a cid ethyl ester Structure

((4-((((Hydroxy...

4-Amino-N-benzolsulfonyl-oxamidsaeure-N'-methylamid Structure

4-Amino-N-benzo...

Ethoxalyl chloride Structure

Ethoxalyl chloride

~80%

((4-((((Methylamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic ac id ethyl ester Structure

((4-((((Methyla...

sulfanilyl-oxalamide Structure

sulfanilyl-oxalamide

Ethoxalyl chloride Structure

Ethoxalyl chloride

~78%

((4-(((Aminoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic acid ethyl es ter Structure

((4-(((Aminoace...

Ethoxalyl chloride Structure

Ethoxalyl chloride

N1-((4-aminophenyl)sulfonyl)-N2-propyloxalamide Structure

N1-((4-aminophe...

~82%

ethyl [4-[(propylcarbamoylformyl)sulfamoyl]phenyl]carbamoylformate Structure

ethyl [4-[(prop...

Ethoxalyl chloride Structure

Ethoxalyl chloride

N1-((4-aminophenyl)sulfonyl)-N2-isobutyloxalamide Structure

N1-((4-aminophe...

~80%

ethyl 2-[4-[[2-(2-methylpropylamino)-2-oxoacetyl]sulfamoyl]anilino]-2-oxoacetate Structure

ethyl 2-[4-[[2-...

((4-((((Methylamino)oxoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic ac id ethyl ester Structure

((4-((((Methyla...

Benzylamine Structure

~72%

N'-benzyl-N'-[4-[[2-(methylamino)-2-oxoacetyl]sulfamoyl]phenyl]oxamide Structure

N'-benzyl-N'-[4...

4-Amino-N-benzolsulfonyl-oxamidsaeure-N'-methylamid Structure

4-Amino-N-benzo...

~%

N'-benzyl-N'-[4-[[2-(methylamino)-2-oxoacetyl]sulfamoyl]phenyl]oxamide Structure

N'-benzyl-N'-[4...

p-(N-Ethoxalylamino)benzenesulfonyloxamic acid ethyl ester Structure

p-(N-Ethoxalyla...

~90%

((4-((Aminooxoacetyl)amino)phenyl)sulfonyl)ethanediamide Structure

((4-((Aminooxoa...

((4-(((Aminoacetyl)amino)sulfonyl)phenyl)amino)oxoacetic acid ethyl es ter Structure

((4-(((Aminoace...

~84%

((4-((Aminooxoacetyl)amino)phenyl)sulfonyl)ethanediamide Structure

((4-((Aminooxoa...

N-(4-Amino-benzolsulfonyl)-oxamidsaeure-ethylester Structure

N-(4-Amino-benz...

~%

((4-((Aminooxoacetyl)amino)phenyl)sulfonyl)ethanediamide Structure

((4-((Aminooxoa...

sulfanilyl-oxalamide Structure

sulfanilyl-oxalamide

~%

((4-((Aminooxoacetyl)amino)phenyl)sulfonyl)ethanediamide Structure

((4-((Aminooxoa...

ethyl [4-[(propylcarbamoylformyl)sulfamoyl]phenyl]carbamoylformate Structure

ethyl [4-[(prop...

~71%

N'-[4-[[2-(hydroxyamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N-propyloxamide Structure

N'-[4-[[2-(hydr...

N1-((4-aminophenyl)sulfonyl)-N2-propyloxalamide Structure

N1-((4-aminophe...

~%

N'-[4-[[2-(hydroxyamino)-2-oxoacetyl]amino]phenyl]sulfonyl-N-propyloxamide Structure

N'-[4-[[2-(hydr...