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

Synthesis and antiviral activity of sulfonamidobenzophenone oximes and sulfonamidobenzamides

M Ogata, H Matsumoto, S Shimizu, S Kida…

Index: Ogata, Masaru; Matsumoto, Hiroshi; Shimizu, Sumio; Kida, Shiro; Wada, Toru; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 3 p. 417 - 423

Full Text: HTML

Citation Number: 12

Abstract

To find antiviral agents, various sulfonamidobenzophenone oximes (11) were synthesized from the appropriate m-sulfonamidobenzophenones by hydroxylamine reaction. The reaction products were generally obtained as syn/anti mixtures which were separable by fractional crystallization. The anti isomer had more potent antipoliovirus activity than the syn isomer. Various sulfonamidobenzamides (111) which were structurally related to I1 were ...

2-NITROBENZANILIDE Structure

2-NITROBENZANILIDE

~%

2-(dimethylsulfamoylamino)-N-phenylbenzamide Structure

2-(dimethylsulf...

Structure

~%

2-(dimethylsulfamoylamino)-N-phenylbenzamide Structure

2-(dimethylsulf...

2-Nitrobenzoyl chloride Structure

2-Nitrobenzoyl ...

~%

2-(dimethylsulfamoylamino)-N-phenylbenzamide Structure

2-(dimethylsulf...

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

2'-aminobenzanilide Structure

2'-aminobenzanilide

~%

2-(dimethylsulfamoylamino)-N-phenylbenzamide Structure

2-(dimethylsulf...

2-Aminopyridine Structure

2-Aminopyridine

~%

3-(dimethylsulfamoylamino)-N-pyridin-2-ylbenzamide Structure

3-(dimethylsulf...

3-nitro-N-pyridin-2-ylbenzamide Structure

3-nitro-N-pyrid...

~%

3-(dimethylsulfamoylamino)-N-pyridin-2-ylbenzamide Structure

3-(dimethylsulf...

3-Nitrobenzoyl chloride Structure

3-Nitrobenzoyl ...

~%

3-(dimethylsulfamoylamino)-N-pyridin-2-ylbenzamide Structure

3-(dimethylsulf...

3-amino-N-pyridin-2-yl-benzamide Structure

3-amino-N-pyrid...

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

~%

3-(dimethylsulfamoylamino)-N-pyridin-2-ylbenzamide Structure

3-(dimethylsulf...

Cyclohexylamine Structure

Cyclohexylamine

~%

3-Amino-N-cyclohexylbenzamide Structure

3-Amino-N-cyclo...

3-Nitrobenzoyl chloride Structure

3-Nitrobenzoyl ...

~%

3-Amino-N-cyclohexylbenzamide Structure

3-Amino-N-cyclo...

N-(4-n-Butylphenyl)-4-nitrobenzamide Structure

N-(4-n-Butylphe...

~%

4-amino-N-(4-butylphenyl)benzamide Structure

4-amino-N-(4-bu...

4-Butylaniline Structure

~%

4-amino-N-(4-butylphenyl)benzamide Structure

4-amino-N-(4-bu...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

4-amino-N-(4-butylphenyl)benzamide Structure

4-amino-N-(4-bu...

N-(4-methoxyphenyl)-3-nitrobenzamide Structure

N-(4-methoxyphe...

~%

3-(dimethylsulfamoylamino)-N-(4-methoxyphenyl)benzamide Structure

3-(dimethylsulf...

p-Anisidine Structure

~%

3-(dimethylsulfamoylamino)-N-(4-methoxyphenyl)benzamide Structure

3-(dimethylsulf...

3-Nitrobenzoyl chloride Structure

3-Nitrobenzoyl ...

~%

3-(dimethylsulfamoylamino)-N-(4-methoxyphenyl)benzamide Structure

3-(dimethylsulf...

3-amino-N-(4-methoxyphenyl)benzamide Structure

3-amino-N-(4-me...

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

~%

3-(dimethylsulfamoylamino)-N-(4-methoxyphenyl)benzamide Structure

3-(dimethylsulf...

Tricaine Structure

~%

N-(2-acetylphenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(2-acetylphen...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(2-acetylphenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(2-acetylphen...

Tricaine Structure

~%

N-(3-nitrophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(3-nitropheny...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(3-nitrophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(3-nitropheny...

Tricaine Structure

~%

N-(2-aminophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(2-aminopheny...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(2-aminophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(2-aminopheny...

4-chloro-3-((N,N-dimethylsulfamoyl)amino)benzoic acid Structure

4-chloro-3-((N,...

~%

4-chloro-3-(dimethylsulfamoylamino)-N-phenylbenzamide Structure

4-chloro-3-(dim...

3-Chloroaniline Structure

3-Chloroaniline

~%

3-amino-3'-chlorobenzanilide Structure

3-amino-3'-chlo...

3-Nitrobenzoyl chloride Structure

3-Nitrobenzoyl ...

~%

3-amino-3'-chlorobenzanilide Structure

3-amino-3'-chlo...

N-(4-cyanophenyl)-3-nitrobenzamide Structure

N-(4-cyanopheny...

~%

N-(4-cyanophenyl)-3-(dimethylsulfamoylamino)benzamide Structure

N-(4-cyanopheny...

4-Aminobenzonitrile Structure

4-Aminobenzonitrile

~%

N-(4-cyanophenyl)-3-(dimethylsulfamoylamino)benzamide Structure

N-(4-cyanopheny...

3-Nitrobenzoyl chloride Structure

3-Nitrobenzoyl ...

~%

N-(4-cyanophenyl)-3-(dimethylsulfamoylamino)benzamide Structure

N-(4-cyanopheny...

N/A Structure

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

~%

N-(4-cyanophenyl)-3-(dimethylsulfamoylamino)benzamide Structure

N-(4-cyanopheny...

Benzamide,3-nitro-N-phenyl- Structure

Benzamide,3-nit...

~%

N-phenyl-3-(pyrrolidin-1-ylsulfonylamino)benzamide Structure

N-phenyl-3-(pyr...

1-Pyrrolidinesulfonyl chloride Structure

1-Pyrrolidinesu...

3-Amino-N-phenylbenzamide Structure

3-Amino-N-pheny...

~%

N-phenyl-3-(pyrrolidin-1-ylsulfonylamino)benzamide Structure

N-phenyl-3-(pyr...

Tricaine Structure

~%

N-(3-chlorophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(3-chlorophen...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(3-chlorophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(3-chlorophen...

Tricaine Structure

~%

N-(4-chlorophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(4-chlorophen...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(4-chlorophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(4-chlorophen...

Benzamide,N-(3-chlorophenyl)-3-nitro- Structure

Benzamide,N-(3-...

~%

3-amino-3'-chlorobenzanilide Structure

3-amino-3'-chlo...

(3-aminophenyl)-(4-methoxyphenyl)methanone Structure

(3-aminophenyl)...

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

~77%

1-(dimethylsulfamoylamino)-3-(4-methoxybenzoyl)benzene Structure

1-(dimethylsulf...

Benzamide,3-nitro-N-phenyl- Structure

Benzamide,3-nit...

~%

N-phenyl-3-(piperidin-1-ylsulfonylamino)benzamide Structure

N-phenyl-3-(pip...

Piperidine-1-sulfonyl chloride Structure

Piperidine-1-su...

3-Amino-N-phenylbenzamide Structure

3-Amino-N-pheny...

~%

N-phenyl-3-(piperidin-1-ylsulfonylamino)benzamide Structure

N-phenyl-3-(pip...

Benzamide,3-nitro-N-phenyl- Structure

Benzamide,3-nit...

~%

3-(methanesulfonamido)-N-phenylbenzamide Structure

3-(methanesulfo...

3-Amino-N-phenylbenzamide Structure

3-Amino-N-pheny...

Methanesulfonyl chloride Structure

Methanesulfonyl...

~%

3-(methanesulfonamido)-N-phenylbenzamide Structure

3-(methanesulfo...

ethyl 4-[(dimethylsulfamoyl)amino]benzoate Structure

ethyl 4-[(dimet...

~%

N-(4-chlorophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(4-chlorophen...

Benzocaine Structure

~%

N-(4-chlorophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(4-chlorophen...

4-([(DIMETHYLAMINO)SULFONYL]AMINO)BENZOIC ACID Structure

4-([(DIMETHYLAM...

~%

N-(4-chlorophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(4-chlorophen...

Cyclohexylamine Structure

Cyclohexylamine

~%

N-cyclohexyl-3-(dimethylsulfamoylamino)benzamide Structure

N-cyclohexyl-3-...

3-Nitrobenzoyl chloride Structure

3-Nitrobenzoyl ...

~%

N-cyclohexyl-3-(dimethylsulfamoylamino)benzamide Structure

N-cyclohexyl-3-...

3-Amino-N-cyclohexylbenzamide Structure

3-Amino-N-cyclo...

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

~%

N-cyclohexyl-3-(dimethylsulfamoylamino)benzamide Structure

N-cyclohexyl-3-...

Tricaine Structure

~%

3-(propan-2-ylsulfonylamino)-N-(1,3-thiazol-2-yl)benzamide Structure

3-(propan-2-yls...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

3-(propan-2-ylsulfonylamino)-N-(1,3-thiazol-2-yl)benzamide Structure

3-(propan-2-yls...

Tricaine Structure

~%

N-tert-butyl-3-(propan-2-ylsulfonylamino)benzamide Structure

N-tert-butyl-3-...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-tert-butyl-3-(propan-2-ylsulfonylamino)benzamide Structure

N-tert-butyl-3-...

3-Chloroaniline Structure

3-Chloroaniline

3-Nitrobenzoyl chloride Structure

3-Nitrobenzoyl ...

~%

Benzamide,N-(3-chlorophenyl)-3-nitro- Structure

Benzamide,N-(3-...

Benzamide,3-nitro-N-phenyl- Structure

Benzamide,3-nit...

~%

3-(benzenesulfonamido)-N-phenylbenzamide Structure

3-(benzenesulfo...

3-Amino-N-phenylbenzamide Structure

3-Amino-N-pheny...

chlorophenylsulfone Structure

chlorophenylsulfone

~%

3-(benzenesulfonamido)-N-phenylbenzamide Structure

3-(benzenesulfo...

Benzamide,N-(3-chlorophenyl)-3-nitro- Structure

Benzamide,N-(3-...

~%

N-(3-chlorophenyl)-3-(dimethylsulfamoylamino)benzamide Structure

N-(3-chlorophen...

3-Chloroaniline Structure

3-Chloroaniline

~%

N-(3-chlorophenyl)-3-(dimethylsulfamoylamino)benzamide Structure

N-(3-chlorophen...

3-Nitrobenzoyl chloride Structure

3-Nitrobenzoyl ...

~%

N-(3-chlorophenyl)-3-(dimethylsulfamoylamino)benzamide Structure

N-(3-chlorophen...

3-amino-3'-chlorobenzanilide Structure

3-amino-3'-chlo...

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

~%

N-(3-chlorophenyl)-3-(dimethylsulfamoylamino)benzamide Structure

N-(3-chlorophen...

ethyl 4-[(dimethylsulfamoyl)amino]benzoate Structure

ethyl 4-[(dimet...

~%

N-(3-chlorophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(3-chlorophen...

Benzocaine Structure

~%

N-(3-chlorophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(3-chlorophen...

4-([(DIMETHYLAMINO)SULFONYL]AMINO)BENZOIC ACID Structure

4-([(DIMETHYLAM...

~%

N-(3-chlorophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(3-chlorophen...

Tricaine Structure

~%

N-benzhydryl-3-(propan-2-ylsulfonylamino)benzamide Structure

N-benzhydryl-3-...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-benzhydryl-3-(propan-2-ylsulfonylamino)benzamide Structure

N-benzhydryl-3-...

Tricaine Structure

~%

N-(furan-2-ylmethyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(furan-2-ylme...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(furan-2-ylmethyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(furan-2-ylme...

N-(4-bromophenyl)-4-nitrobenzamide Structure

N-(4-bromopheny...

~%

4-amino-N-(4-bromophenyl)benzamide Structure

4-amino-N-(4-br...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

4-amino-N-(4-bromophenyl)benzamide Structure

4-amino-N-(4-br...

4-Bromoaniline Structure

~%

4-amino-N-(4-bromophenyl)benzamide Structure

4-amino-N-(4-br...

Benzamide,3-nitro-N-phenyl- Structure

Benzamide,3-nit...

~%

N-phenyl-3-(propan-2-ylsulfonylamino)benzamide Structure

N-phenyl-3-(pro...

ISOPROPYLSULFONYL CHLORIDE Structure

ISOPROPYLSULFON...

3-Amino-N-phenylbenzamide Structure

3-Amino-N-pheny...

~%

N-phenyl-3-(propan-2-ylsulfonylamino)benzamide Structure

N-phenyl-3-(pro...

Tricaine Structure

~%

N-(3-hydroxyphenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(3-hydroxyphe...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(3-hydroxyphenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(3-hydroxyphe...

ethyl 4-[(dimethylsulfamoyl)amino]benzoate Structure

ethyl 4-[(dimet...

~%

N-(2-chlorophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(2-chlorophen...

4-([(DIMETHYLAMINO)SULFONYL]AMINO)BENZOIC ACID Structure

4-([(DIMETHYLAM...

~%

N-(2-chlorophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(2-chlorophen...

Tricaine Structure

~%

N-(4-bromophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(4-bromopheny...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(4-bromophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(4-bromopheny...

Tricaine Structure

~%

N-(4-fluorophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(4-fluorophen...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(4-fluorophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(4-fluorophen...

Tricaine Structure

~%

N-benzyl-3-(propan-2-ylsulfonylamino)benzamide Structure

N-benzyl-3-(pro...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-benzyl-3-(propan-2-ylsulfonylamino)benzamide Structure

N-benzyl-3-(pro...

4-(propane-2-sulfonylamino)benzoic acid Structure

4-(propane-2-su...

~%

4-(propan-2-ylsulfonylamino)benzoyl chloride Structure

4-(propan-2-yls...

Aethyl-4-(2-propansulfonamido)benzoat Structure

Aethyl-4-(2-pro...

~%

4-(propan-2-ylsulfonylamino)benzoyl chloride Structure

4-(propan-2-yls...

Benzocaine Structure

~%

4-(propan-2-ylsulfonylamino)benzoyl chloride Structure

4-(propan-2-yls...

Benzocaine Structure

~%

N-(2-chlorophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(2-chlorophen...

N-(4-bromophenyl)-4-nitrobenzamide Structure

N-(4-bromopheny...

~%

N-(4-bromophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(4-bromopheny...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

N-(4-bromophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(4-bromopheny...

4-Bromoaniline Structure

~%

N-(4-bromophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(4-bromopheny...

4-amino-N-(4-bromophenyl)benzamide Structure

4-amino-N-(4-br...

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

~%

N-(4-bromophenyl)-4-(dimethylsulfamoylamino)benzamide Structure

N-(4-bromopheny...

Tricaine Structure

~%

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

Benzamide,4-nitro-N-phenyl- Structure

Benzamide,4-nit...

~%

4-(dimethylsulfamoylamino)-N-phenylbenzamide Structure

4-(dimethylsulf...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

4-(dimethylsulfamoylamino)-N-phenylbenzamide Structure

4-(dimethylsulf...

Structure

~%

4-(dimethylsulfamoylamino)-N-phenylbenzamide Structure

4-(dimethylsulf...

Benzamide,4-amino-N-phenyl- Structure

Benzamide,4-ami...

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

~%

4-(dimethylsulfamoylamino)-N-phenylbenzamide Structure

4-(dimethylsulf...

Tricaine Structure

~%

N-(3,4-dichlorophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(3,4-dichloro...

3-(propan-2-ylsulfonylamino)benzoic acid Structure

3-(propan-2-yls...

~%

N-(3,4-dichlorophenyl)-3-(propan-2-ylsulfonylamino)benzamide Structure

N-(3,4-dichloro...

N-(4-methylphenyl)-4-nitrobenzamide Structure

N-(4-methylphen...

~%

4-(dimethylsulfamoylamino)-N-(4-methylphenyl)benzamide Structure

4-(dimethylsulf...

p-Toluidine Structure

~%

4-(dimethylsulfamoylamino)-N-(4-methylphenyl)benzamide Structure

4-(dimethylsulf...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

4-(dimethylsulfamoylamino)-N-(4-methylphenyl)benzamide Structure

4-(dimethylsulf...

3-(2-FLUOROPHENYL)PIPERIDINE HYDROCHLORIDE Structure

3-(2-FLUOROPHEN...

Dimethylsulfamoyl chloride Structure

Dimethylsulfamo...

~%

4-(dimethylsulfamoylamino)-N-(4-methylphenyl)benzamide Structure

4-(dimethylsulf...

ethyl 4-[(dimethylsulfamoyl)amino]benzoate Structure

ethyl 4-[(dimet...

~%

4-(dimethylsulfamoylamino)-N-(4-ethylphenyl)benzamide Structure

4-(dimethylsulf...

Benzocaine Structure

~%

4-(dimethylsulfamoylamino)-N-(4-ethylphenyl)benzamide Structure

4-(dimethylsulf...

4-([(DIMETHYLAMINO)SULFONYL]AMINO)BENZOIC ACID Structure

4-([(DIMETHYLAM...

~%

4-(dimethylsulfamoylamino)-N-(4-ethylphenyl)benzamide Structure

4-(dimethylsulf...

ethyl 4-[(dimethylsulfamoyl)amino]benzoate Structure

ethyl 4-[(dimet...

~%

4-(dimethylsulfamoylamino)-N-(4-iodophenyl)benzamide Structure

4-(dimethylsulf...

Benzocaine Structure

~%

4-(dimethylsulfamoylamino)-N-(4-iodophenyl)benzamide Structure

4-(dimethylsulf...

4-([(DIMETHYLAMINO)SULFONYL]AMINO)BENZOIC ACID Structure

4-([(DIMETHYLAM...

~%

4-(dimethylsulfamoylamino)-N-(4-iodophenyl)benzamide Structure

4-(dimethylsulf...

ethyl 4-[(dimethylsulfamoyl)amino]benzoate Structure

ethyl 4-[(dimet...

~%

4-([(DIMETHYLAMINO)SULFONYL]AMINO)BENZOIC ACID Structure

4-([(DIMETHYLAM...

Benzocaine Structure

~%

4-([(DIMETHYLAMINO)SULFONYL]AMINO)BENZOIC ACID Structure

4-([(DIMETHYLAM...