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

Synthesis and antibacterial activity of 2, 2'-dithiobis (benzamide) derivatives against Mycobacterium species

R Okachi, H Niino, K Kitaura, K Mineura…

Index: Okachi, Ryo; Niino, Hideki; Kitaura, Kozo; Mineura, Kazuyuki; Nakamizo, Yoshinobu; et al. Journal of Medicinal Chemistry, 1985 , vol. 28, # 12 p. 1772 - 1779

Full Text: HTML

Citation Number: 36

Abstract

A series of compounds, which are analogues of 2, 2 '-dithiobis (benzamide), were synthesized and tested for in vitro antibacterial activity against Mycobacterium tuberculosis H37Rv including resistant strains against streptomycin, kanamycin, or isonicotinic acid hydrazide. MICs of these compounds against atypical mycobacteria, Mycobacterium kansasii and Mycobacterium intracellulare were also examined. Structure-activity ...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

Dibutylamine Structure

~93%

N,N-dibutyl-2-[[2-(dibutylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N,N-dibutyl-2-[...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

phthalimide Structure

~79%

2-[2-[[2-(1,3-dioxoisoindole-2-carbonyl)phenyl]disulfanyl]benzoyl]isoindole-1,3-dione Structure

2-[2-[[2-(1,3-d...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

2-[2-[[2-(1,3-dioxoisoindole-2-carbonyl)phenyl]disulfanyl]benzoyl]isoindole-1,3-dione Structure

2-[2-[[2-(1,3-d...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

Diphenylamine Structure

~58%

2-[[2-(diphenylcarbamoyl)phenyl]disulfanyl]-N,N-diphenylbenzamide Structure

2-[[2-(diphenyl...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

2-[[2-(diphenylcarbamoyl)phenyl]disulfanyl]-N,N-diphenylbenzamide Structure

2-[[2-(diphenyl...

N-(2-hydroxyethyl)-2-[[2-(2-hydroxyethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(2-hydroxyeth...

Dodecanoyl chloride Structure

Dodecanoyl chloride

~%

2-[[2-[[2-(2-dodecanoyloxyethylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]ethyl dodecanoate Structure

2-[[2-[[2-(2-do...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

3,5-diethylaniline Structure

3,5-diethylaniline

~73%

N-(3,5-diethylphenyl)-2-[[2-[(3,5-diethylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(3,5-diethylp...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(3,5-diethylphenyl)-2-[[2-[(3,5-diethylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(3,5-diethylp...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

1-Naphthalenamine,4-chloro- Structure

1-Naphthalenami...

~79%

N-(4-chloronaphthalen-1-yl)-2-[[2-[(4-chloronaphthalen-1-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(4-chloronaph...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(4-chloronaphthalen-1-yl)-2-[[2-[(4-chloronaphthalen-1-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(4-chloronaph...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

4-Aminomethyl piperidine Structure

4-Aminomethyl p...

~74%

N-(piperidin-4-ylmethyl)-2-[[2-(piperidin-4-ylmethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(piperidin-4-...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(piperidin-4-ylmethyl)-2-[[2-(piperidin-4-ylmethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(piperidin-4-...

2,2'-dithiobis(N-2-hydroxypropylbenzamide) Structure

2,2'-dithiobis(...

~%

2-(2-hydroxypropyl)-1,2-benzothiazol-3-one Structure

2-(2-hydroxypro...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

Furfurylamine Structure

~89%

N-(furan-2-ylmethyl)-2-[[2-(furan-2-ylmethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(furan-2-ylme...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(furan-2-ylmethyl)-2-[[2-(furan-2-ylmethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(furan-2-ylme...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

4-phenylbutan-2-amine Structure

4-phenylbutan-2...

~87%

N-(4-phenylbutan-2-yl)-2-[[2-(4-phenylbutan-2-ylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(4-phenylbuta...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(4-phenylbutan-2-yl)-2-[[2-(4-phenylbutan-2-ylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(4-phenylbuta...

N-(2-hydroxyethyl)-2-[[2-(2-hydroxyethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(2-hydroxyeth...

Palmitoyl chloride Structure

Palmitoyl chloride

~%

2-[[2-[[2-(2-hexadecanoyloxyethylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]ethyl hexadecanoate Structure

2-[[2-[[2-(2-he...

N-(3-hydroxypropyl)-2-[[2-(3-hydroxypropylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(3-hydroxypro...

Palmitoyl chloride Structure

Palmitoyl chloride

~%

3-[[2-[[2-(3-pentadecanoyloxypropylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]propyl hexadecanoate Structure

3-[[2-[[2-(3-pe...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

2-Amino-3-naphthol Structure

2-Amino-3-naphthol

~78%

N-(3-hydroxynaphthalen-2-yl)-2-[[2-[(3-hydroxynaphthalen-2-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(3-hydroxynap...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(3-hydroxynaphthalen-2-yl)-2-[[2-[(3-hydroxynaphthalen-2-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(3-hydroxynap...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

Benzenesulfonamide,4-amino-N-2-benzothiazolyl- Structure

Benzenesulfonam...

~76%

N-[4-(1,3-benzothiazol-2-ylsulfamoyl)phenyl]-2-[[2-[[4-(1,3-benzothiazol-2-ylsulfamoyl)phenyl]carbamoyl]phenyl]disulfanyl]benzamide Structure

N-[4-(1,3-benzo...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-[4-(1,3-benzothiazol-2-ylsulfamoyl)phenyl]-2-[[2-[[4-(1,3-benzothiazol-2-ylsulfamoyl)phenyl]carbamoyl]phenyl]disulfanyl]benzamide Structure

N-[4-(1,3-benzo...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

4-Bromo-1-naphthalenamine Structure

4-Bromo-1-napht...

~93%

N-(4-bromonaphthalen-1-yl)-2-[[2-[(4-bromonaphthalen-1-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(4-bromonapht...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(4-bromonaphthalen-1-yl)-2-[[2-[(4-bromonaphthalen-1-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(4-bromonapht...

Dodecanoyl chloride Structure

Dodecanoyl chloride

2,2'-dithiobis(N-2-hydroxypropylbenzamide) Structure

2,2'-dithiobis(...

~%

1-[[2-[[2-(2-dodecanoyloxypropylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]propan-2-yl dodecanoate Structure

1-[[2-[[2-(2-do...

2,2'-dithiobis(N-2-hydroxypropylbenzamide) Structure

2,2'-dithiobis(...

Palmitoyl chloride Structure

Palmitoyl chloride

~%

1-[[2-[[2-(2-hexadecanoyloxypropylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]propan-2-yl hexadecanoate Structure

1-[[2-[[2-(2-he...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

2-Ethylhexylamine Structure

2-Ethylhexylamine

~94%

N-(2-ethylhexyl)-2-[[2-(2-ethylhexylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(2-ethylhexyl...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(2-ethylhexyl)-2-[[2-(2-ethylhexylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(2-ethylhexyl...

N-(2-hydroxyethyl)-2-[[2-(2-hydroxyethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(2-hydroxyeth...

Ethyl isocyanate Structure

Ethyl isocyanate

~92%

2-[[2-[[2-[2-(ethylcarbamoyloxy)ethylcarbamoyl]phenyl]disulfanyl]benzoyl]amino]ethyl N-ethylcarbamate Structure

2-[[2-[[2-[2-(e...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

2-Amino-2-ethyl-1,3-propanediol Structure

2-Amino-2-ethyl...

~88%

N-[1-hydroxy-2-(hydroxymethyl)butan-2-yl]-2-[[2-[[1-hydroxy-2-(hydroxymethyl)butan-2-yl]carbamoyl]phenyl]disulfanyl]benzamide Structure

N-[1-hydroxy-2-...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-[1-hydroxy-2-(hydroxymethyl)butan-2-yl]-2-[[2-[[1-hydroxy-2-(hydroxymethyl)butan-2-yl]carbamoyl]phenyl]disulfanyl]benzamide Structure

N-[1-hydroxy-2-...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

1-Naphthalenemethylamine Structure

1-Naphthaleneme...

~92%

N-(naphthalen-1-ylmethyl)-2-[[2-(naphthalen-1-ylmethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(naphthalen-1...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(naphthalen-1-ylmethyl)-2-[[2-(naphthalen-1-ylmethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(naphthalen-1...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

8-Aminoquinoline Structure

8-Aminoquinoline

~85%

N-quinolin-8-yl-2-[[2-(quinolin-8-ylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-quinolin-8-yl...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-quinolin-8-yl-2-[[2-(quinolin-8-ylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-quinolin-8-yl...

N-(3-hydroxypropyl)-2-[[2-(3-hydroxypropylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(3-hydroxypro...

Butyryl chloride Structure

Butyryl chloride

~%

3-[[2-[[2-(3-butanoyloxypropylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]propyl butanoate Structure

3-[[2-[[2-(3-bu...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

2-nitro-1-naphthylamine Structure

2-nitro-1-napht...

~79%

N-(2-nitronaphthalen-1-yl)-2-[[2-[(2-nitronaphthalen-1-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(2-nitronapht...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(2-nitronaphthalen-1-yl)-2-[[2-[(2-nitronaphthalen-1-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(2-nitronapht...

N-(3-hydroxypropyl)-2-[[2-(3-hydroxypropylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(3-hydroxypro...

Heptanoyl chloride Structure

Heptanoyl chloride

~%

3-[[2-[[2-(3-heptanoyloxypropylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]propyl heptanoate Structure

3-[[2-[[2-(3-he...

N-(3-hydroxypropyl)-2-[[2-(3-hydroxypropylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(3-hydroxypro...

Octanoyl chloride Structure

Octanoyl chloride

~%

3-[[2-[[2-(3-octanoyloxypropylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]propyl octanoate Structure

3-[[2-[[2-(3-oc...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

1-Amino-2-butanol Structure

1-Amino-2-butanol

~87%

N-(2-hydroxybutyl)-2-[[2-(2-hydroxybutylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(2-hydroxybut...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(2-hydroxybutyl)-2-[[2-(2-hydroxybutylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(2-hydroxybut...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

2,2-Dimethoxyethanamine Structure

2,2-Dimethoxyet...

~76%

N-(2,2-dimethoxyethyl)-2-[[2-(2,2-dimethoxyethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(2,2-dimethox...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(2,2-dimethoxyethyl)-2-[[2-(2,2-dimethoxyethylcarbamoyl)phenyl]disulfanyl]benzamide Structure

N-(2,2-dimethox...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

3-Amino-9-ethylcarbazole Structure

3-Amino-9-ethyl...

~66%

N-(9-ethylcarbazol-3-yl)-2-[[2-[(9-ethylcarbazol-3-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(9-ethylcarba...

2,2′-dithiodibenzoic acid Structure

2,2′-dithiodibe...

~%

N-(9-ethylcarbazol-3-yl)-2-[[2-[(9-ethylcarbazol-3-yl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(9-ethylcarba...

2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Structure

2-[(2-carbonoch...

Ethyl glycinate Structure

Ethyl glycinate

~91%

ethyl 2-[[2-[[2-[(2-ethoxy-2-oxoethyl)carbamoyl]phenyl]disulfanyl]benzoyl]amino]acetate Structure

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