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Review Article

Medicinal significance of benzothiazole scaffold: an insight view

, , , &
Pages 240-266 | Received 22 May 2012, Accepted 09 Aug 2012, Published online: 03 Oct 2012

Figures & data

Figure 1.  Chemical structures of riluzole (3) and 1,3-benzothiazole (4).

Figure 1.  Chemical structures of riluzole (3) and 1,3-benzothiazole (4).

Figure 2.  Chemical structure of 2-aryl-substituted (o-hydroxy (5), o-methoxy (6), m-bromo (7), o-nitro (8) and 4-pyridyl (9)) benzothiazole.

Figure 2.  Chemical structure of 2-aryl-substituted (o-hydroxy (5), o-methoxy (6), m-bromo (7), o-nitro (8) and 4-pyridyl (9)) benzothiazole.

Figure 3.  Chemical structure of 2-(substituted-phenyl)benzothiazole derivatives.

Figure 3.  Chemical structure of 2-(substituted-phenyl)benzothiazole derivatives.

Figure 4.  Chemical structure of 2-phenyl-1,3-benzothiazole derivatives.

Figure 4.  Chemical structure of 2-phenyl-1,3-benzothiazole derivatives.

Figure 5.  Chemical structure of fluorinated benzothiazole-substituted-4-hydroxycyclohexa-2,5-dienones.

Figure 5.  Chemical structure of fluorinated benzothiazole-substituted-4-hydroxycyclohexa-2,5-dienones.

Figure 6.  Chemical structure of antitumour benzothiazole derivatives.

Figure 6.  Chemical structure of antitumour benzothiazole derivatives.

Figure 7.  Chemical structure of benzothiazole derivatives.

Figure 7.  Chemical structure of benzothiazole derivatives.

Figure 8.  Chemical structure of substituted 2-phenyl-benzothiazoles.

Figure 8.  Chemical structure of substituted 2-phenyl-benzothiazoles.

Figure 9.  Chemical structure of benzothiazole derivatives containing piperazino-arylsulfonamides, arylthiol and sulphonamides moieties.

Figure 9.  Chemical structure of benzothiazole derivatives containing piperazino-arylsulfonamides, arylthiol and sulphonamides moieties.

Figure 10.  Chemical structure of prop-2-eneamido, 1-acetyl-pyrazoline and thiazolyl substituted 2-aminobenzothiazoles.

Figure 10.  Chemical structure of prop-2-eneamido, 1-acetyl-pyrazoline and thiazolyl substituted 2-aminobenzothiazoles.

Figure 11.  Chemical structure of N-(5-fluorobenzothiaol-2-yl)-2-guanidinothiazole-4-carboxamide.

Figure 11.  Chemical structure of N-(5-fluorobenzothiaol-2-yl)-2-guanidinothiazole-4-carboxamide.

Figure 12.  Chemical structure of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole.

Figure 12.  Chemical structure of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole.

Figure 13.  Chemical structure of 2-(amino-phenyl)benzothiazole.

Figure 13.  Chemical structure of 2-(amino-phenyl)benzothiazole.

Figure 14.  Chemical structure of antiproliferative 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazoles.

Figure 14.  Chemical structure of antiproliferative 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazoles.

Figure 15.  Chemical structure of 2-acetyl-3-(6-methoxy-benzothiazo)-2-yl-amino-acrylonitrile.

Figure 15.  Chemical structure of 2-acetyl-3-(6-methoxy-benzothiazo)-2-yl-amino-acrylonitrile.

Figure 16.  Chemical structure of amidino-nitro and amidino-amino substituted benzothiazoles.

Figure 16.  Chemical structure of amidino-nitro and amidino-amino substituted benzothiazoles.

Figure 17.  Chemical structure of various substituted imidazobenzothiazole.

Figure 17.  Chemical structure of various substituted imidazobenzothiazole.

Figure 18.  Chemical structure of 2-(4-aminophenyl)benzothiazole derivatives.

Figure 18.  Chemical structure of 2-(4-aminophenyl)benzothiazole derivatives.

Figure 19.  Chemical structure of hydroxylated 2-phenylbenzothiazoles.

Figure 19.  Chemical structure of hydroxylated 2-phenylbenzothiazoles.

Figure 20.  Chemical Structures of benzo[d]isothiazole, benzothiazole and thiazole Schiff's bases.

Figure 20.  Chemical Structures of benzo[d]isothiazole, benzothiazole and thiazole Schiff's bases.

Figure 21.  Chemical structure of 2,6-dichloro-N-[2-(cyclopropanecarbonylamino) benzothiazole-6-yl]benzamides.

Figure 21.  Chemical structure of 2,6-dichloro-N-[2-(cyclopropanecarbonylamino) benzothiazole-6-yl]benzamides.

Figure 22.  Chemical structure of Benzothiazole derivatives.

Figure 22.  Chemical structure of Benzothiazole derivatives.

Figure 23.  Chemical structure of 2-(4-aminophenyl)benzothiazole derivatives.

Figure 23.  Chemical structure of 2-(4-aminophenyl)benzothiazole derivatives.

Figure 24.  Chemical structure of fluorinated benzothiazole derivatives.

Figure 24.  Chemical structure of fluorinated benzothiazole derivatives.

Figure 25.  Chemical structure of 4-thiazolidinone benzothiazole derivatives.

Figure 25.  Chemical structure of 4-thiazolidinone benzothiazole derivatives.

Figure 26.  Chemical structure of 2-(5-substituted-1,3,4-oxadiazole-2-yl)-1,3-benzothiazole derivatives.

Figure 26.  Chemical structure of 2-(5-substituted-1,3,4-oxadiazole-2-yl)-1,3-benzothiazole derivatives.

Figure 27.  Chemical structure of benzothiazole derivatives.

Figure 27.  Chemical structure of benzothiazole derivatives.

Figure 28.  Chemical structure of substituted benzothiazolium derivatives.

Figure 28.  Chemical structure of substituted benzothiazolium derivatives.

Figure 29.  Chemical structure of 2-styrylbenzothiazole-N-oxides.

Figure 29.  Chemical structure of 2-styrylbenzothiazole-N-oxides.

Figure 30.  Chemical structure of 2,4,6-substituted-1,3,5-tris(benzo-thiazolyl)hexahydro-1,3,5-triazine.

Figure 30.  Chemical structure of 2,4,6-substituted-1,3,5-tris(benzo-thiazolyl)hexahydro-1,3,5-triazine.

Figure 31.  Chemical structure of substituted fluoro-benzothiazole.

Figure 31.  Chemical structure of substituted fluoro-benzothiazole.

Figure 32.  Chemical structure of benzothiazole substituted thiazolidinone.

Figure 32.  Chemical structure of benzothiazole substituted thiazolidinone.

Figure 33.  Chemical structure of substituted 2-alkenyl-6-amino-benzothiazoles.

Figure 33.  Chemical structure of substituted 2-alkenyl-6-amino-benzothiazoles.

Figure 34.  Chemical structure of antifungal 2-amino-substituted-benzothiazoles.

Figure 34.  Chemical structure of antifungal 2-amino-substituted-benzothiazoles.

Figure 35.  Chemical structure of Schiff bases of benzothiazole derivatives.

Figure 35.  Chemical structure of Schiff bases of benzothiazole derivatives.

Figure 36.  Chemical structure of antimicrobial substituted-benzothiazoles.

Figure 36.  Chemical structure of antimicrobial substituted-benzothiazoles.

Figure 37.  Chemical structure of benzothiazole derivatives.

Figure 37.  Chemical structure of benzothiazole derivatives.

Figure 38.  Chemical structure of thiourea derivatives bearing benzothiazole moiety.

Figure 38.  Chemical structure of thiourea derivatives bearing benzothiazole moiety.

Figure 39.  Chemical structure of 4-amino-N-(1,3-benzothiazol-2-yl)benzenesulphonamide.

Figure 39.  Chemical structure of 4-amino-N-(1,3-benzothiazol-2-yl)benzenesulphonamide.

Figure 40.  Chemical structure of 2-mercapto-1,3-benzothiazole derivatives.

Figure 40.  Chemical structure of 2-mercapto-1,3-benzothiazole derivatives.

Figure 41.  Chemical structure of antibacterial benzothiazole derivatives.

Figure 41.  Chemical structure of antibacterial benzothiazole derivatives.

Figure 42.  Chemical structure benzothiazole derivatives.

Figure 42.  Chemical structure benzothiazole derivatives.

Figure 43.  Chemical structure of 15-iminobenzothiazolo[2,3-b]pyrimido[5,6-c]pyrimido[2,3-b]benzothiazole-14(H)-one derivatives.

Figure 43.  Chemical structure of 15-iminobenzothiazolo[2,3-b]pyrimido[5,6-c]pyrimido[2,3-b]benzothiazole-14(H)-one derivatives.

Figure 44.  Chemical structure of substituted pyrimido[2,1-b]benzothiazoles.

Figure 44.  Chemical structure of substituted pyrimido[2,1-b]benzothiazoles.

Figure 45.  Chemical structure of antibacterial flurobenzothiazole derivatives.

Figure 45.  Chemical structure of antibacterial flurobenzothiazole derivatives.

Figure 46.  Chemical structure of 6-amino-2-n-pentylthiobenzothiazole (APB).

Figure 46.  Chemical structure of 6-amino-2-n-pentylthiobenzothiazole (APB).

Figure 47.  Chemical structure of 2-methyl-3-[(substituted)benzothiazole-2′-yl]4(3H)-quinazolinones.

Figure 47.  Chemical structure of 2-methyl-3-[(substituted)benzothiazole-2′-yl]4(3H)-quinazolinones.

Figure 48.  Chemical structure of polyfluorinated 2-benzylthio-benzothiazoles.

Figure 48.  Chemical structure of polyfluorinated 2-benzylthio-benzothiazoles.

Figure 49.  Chemical structure of N-(6-methylbenzothiazolyl)-2,3,5,6-tetrasubstituted-4-(aryl)-1,4-dihydropyridines.

Figure 49.  Chemical structure of N-(6-methylbenzothiazolyl)-2,3,5,6-tetrasubstituted-4-(aryl)-1,4-dihydropyridines.

Figure 50.  Chemical structure of 3,5-diaryl-1-benzothiazolopyrazoline derivatives.

Figure 50.  Chemical structure of 3,5-diaryl-1-benzothiazolopyrazoline derivatives.

Figure 51.  Chemical structure of antiparasitic substituted-benzothiazoles.

Figure 51.  Chemical structure of antiparasitic substituted-benzothiazoles.

Figure 52.  Chemical structure of benzothiazole derivatives.

Figure 52.  Chemical structure of benzothiazole derivatives.

Figure 53.  Chemical structure of antimicrobial benzothiazole derivatives.

Figure 53.  Chemical structure of antimicrobial benzothiazole derivatives.

Figure 54.  Chemical structure of benzothiazole derivatives.

Figure 54.  Chemical structure of benzothiazole derivatives.

Figure 55.  Chemical structure of 2-(p-chlorophenoxymethyl)benzothiazole.

Figure 55.  Chemical structure of 2-(p-chlorophenoxymethyl)benzothiazole.

Figure 56.  Chemical structure of benzothiazole derivatives.

Figure 56.  Chemical structure of benzothiazole derivatives.

Figure 57.  Chemical structure of 5-n-undecyl-6-hydroxy-4,7-dioxobenzothiazole.

Figure 57.  Chemical structure of 5-n-undecyl-6-hydroxy-4,7-dioxobenzothiazole.

Figure 58.  Chemical structure of benzothiazole amino alcohols.

Figure 58.  Chemical structure of benzothiazole amino alcohols.

Figure 59.  Chemical structure of benzothiazole derivatives.

Figure 59.  Chemical structure of benzothiazole derivatives.

Figure 60.  Chemical structure of 2-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-3-nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]-1,8-naphthyridine-6-carboxylic acid.

Figure 60.  Chemical structure of 2-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-3-nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]-1,8-naphthyridine-6-carboxylic acid.

Figure 61.  Chemical structure of 2-methylbenzothiazole derivatives.

Figure 61.  Chemical structure of 2-methylbenzothiazole derivatives.

Figure 62.  Chemical structure of benzothiazoline derivatives.

Figure 62.  Chemical structure of benzothiazoline derivatives.

Figure 63.  Chemical structure of flurobenzothiazole derivatives.

Figure 63.  Chemical structure of flurobenzothiazole derivatives.

Figure 64.  Chemical structure of phenyl imidazo-[2,1-b]benzothiazole derivatives.

Figure 64.  Chemical structure of phenyl imidazo-[2,1-b]benzothiazole derivatives.

Figure  65.  Chemical structure of 2-[[2-alkoxy-6-pentadecylphenyl)methyl]thio]-1H-benzothiazole.

Figure  65.  Chemical structure of 2-[[2-alkoxy-6-pentadecylphenyl)methyl]thio]-1H-benzothiazole.

Figure 66.  Chemical structure of 2-substituted-9-chloro-8-fluoropyrimido [2,1-b]benzothiazole-3-cyano-4(H)-ones.

Figure 66.  Chemical structure of 2-substituted-9-chloro-8-fluoropyrimido [2,1-b]benzothiazole-3-cyano-4(H)-ones.

Figure 67.  Chemical structure of anti-inflammatory 2-amino benzothiazole derivatives.

Figure 67.  Chemical structure of anti-inflammatory 2-amino benzothiazole derivatives.

Figure 68.  Chemical structure of 2-substituted-5-benzothiazoleacetic acid and 6-benzothiazoleacetic-2-substituted acid.

Figure 68.  Chemical structure of 2-substituted-5-benzothiazoleacetic acid and 6-benzothiazoleacetic-2-substituted acid.

Figure 69.  Chemical structure of benzothiazole derivatives.

Figure 69.  Chemical structure of benzothiazole derivatives.

Figure 70.  Chemical structure of anticonvulsant benzothiazoles.

Figure 70.  Chemical structure of anticonvulsant benzothiazoles.

Figure 71.  Chemical structure of 1,3-benzothiazol-2-yl benzamides.

Figure 71.  Chemical structure of 1,3-benzothiazol-2-yl benzamides.

Figure 72.  Chemical structure of 1,3-benzothiazol-2-yl-semicarbazones.

Figure 72.  Chemical structure of 1,3-benzothiazol-2-yl-semicarbazones.

Figure 73.  Chemical structure of series of 2-amino[5'-(4-sulphonylbenzylidine)2,4-thiazolidinedione]-7-chloro-6-fluorobenzothiazoles.

Figure 73.  Chemical structure of series of 2-amino[5'-(4-sulphonylbenzylidine)2,4-thiazolidinedione]-7-chloro-6-fluorobenzothiazoles.

Figure 74.  Chemical structure of 2-thioether-benzothiazoles.

Figure 74.  Chemical structure of 2-thioether-benzothiazoles.

Figure 75.  Chemical structure of benzothiazole derivatives.

Figure 75.  Chemical structure of benzothiazole derivatives.

Figure 76.  Chemical structure of benzothiazole derivatives.

Figure 76.  Chemical structure of benzothiazole derivatives.

Figure 77.  Chemical structure of N-(1,3-benzothiazol-2-yl)-1,1-biphenyl-4-carboxamide.

Figure 77.  Chemical structure of N-(1,3-benzothiazol-2-yl)-1,1-biphenyl-4-carboxamide.

Figure 78.  Chemical structure of coronary vasodilatory active benzothiazole derivatives.

Figure 78.  Chemical structure of coronary vasodilatory active benzothiazole derivatives.

Figure 79.  Chemical structure of triamide derivatives bearing a benzothiazole.

Figure 79.  Chemical structure of triamide derivatives bearing a benzothiazole.

Figure 80.  Chemical structure of antioxidant 2-mercapto-6-methylbenzothiazole.

Figure 80.  Chemical structure of antioxidant 2-mercapto-6-methylbenzothiazole.

Figure 81.  Chemical structure of 3H-spiro[1,3-benzothiazole-2,30-indol]-20(10H)-ones derivatives.

Figure 81.  Chemical structure of 3H-spiro[1,3-benzothiazole-2,30-indol]-20(10H)-ones derivatives.

Figure 82.  Chemical structure of substituted benzothiazole ketone.

Figure 82.  Chemical structure of substituted benzothiazole ketone.

Figure 83.  Chemical structure of phosphodiesterase inhibitor benzothiazole derivatives.

Figure 83.  Chemical structure of phosphodiesterase inhibitor benzothiazole derivatives.

Figure 84.  Chemical structure of benzothiazole derivatives.

Figure 84.  Chemical structure of benzothiazole derivatives.

Figure 85.  Chemical structure of 2-arylbenzothiazole derivatives.

Figure 85.  Chemical structure of 2-arylbenzothiazole derivatives.

Figure 86.  Chemical structure of benzothiazole derivatives having A β-fibril binding affinity.

Figure 86.  Chemical structure of benzothiazole derivatives having A β-fibril binding affinity.

Table 1.  Some successful benzothiazole based clinically available drugs.

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