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

Imdazole systems. I. Imidzo [2, 1??b][1, 3, 5] benzothiadiazepine derivatives as potential antipsychotic agents

LD Vecchia, J Dellureficio, B Kisis…

Index: Della Vecchia; Dellureficio; Kisis; Vlattas Journal of Heterocyclic Chemistry, 1983 , vol. 20, # 5 p. 1287 - 1294

Full Text: HTML

Citation Number: 7

Abstract

Abstract Imidazo [2, 1-b][1, 3, 5] benzothiadiazepine 3 constitutes a novel ring system, and its analogs 3a-i were synthesized to investigate their potential antipsychotic activity. The synthesis of the ring system was achieved by reaction of 2-aminophenylthioimidazoles 7 with phosgene or thiophosgene and by ring closure of the 1-[2-(2-imidazolyl) thiophenyliminocarbonyl]-1-piperazines 13. An efficient method for the conversion of ...

4-methyl-1,3-dihydroimidazole-2-thione Structure

4-methyl-1,3-di...

2-Nitrochlorobenzene Structure

2-Nitrochlorobenzene

~81%

5-methyl-2-(2-nitrophenyl)sulfanyl-1H-imidazole Structure

5-methyl-2-(2-n...

2-(4-chloro-2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(4-chloro-2-n...

~80%

5-chloro-2-(1H-imidazol-2-ylsulfanyl)aniline Structure

5-chloro-2-(1H-...

1-Bromo-2-nitrobenzene Structure

1-Bromo-2-nitro...

2-MERCAPTOIMIDAZOLE Structure

2-MERCAPTOIMIDAZOLE

~84%

2-(2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(2-nitropheny...

2-(2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(2-nitropheny...

~84%

2-(1H-imidazol-2-ylsulfanyl)aniline Structure

2-(1H-imidazol-...

1-Bromo-2-nitrobenzene Structure

1-Bromo-2-nitro...

~%

2-(1H-imidazol-2-ylsulfanyl)aniline Structure

2-(1H-imidazol-...

methylpiperazine Structure

methylpiperazine

5-methylthioimidazo[2,1-b][1,3,5]benzothiadiazepine Structure

5-methylthioimi...

~55%

Pentiapine Structure

1-Bromo-2-nitrobenzene Structure

1-Bromo-2-nitro...

~%

Pentiapine Structure

2-(1H-imidazol-2-ylsulfanyl)aniline Structure

2-(1H-imidazol-...

~%

Pentiapine Structure

2-(2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(2-nitropheny...

~%

Pentiapine Structure

imidazo[2,1-b][1,3,5]benzothiadiazepine-5(6H)-thione Structure

imidazo[2,1-b][...

~%

Pentiapine Structure

methylpiperazine Structure

methylpiperazine

~%

Pentiapine Structure

imidazo[2,1-b][1,3,5]benzothiadiazepine-5(6H)-one Structure

imidazo[2,1-b][...

~%

Pentiapine Structure

Cyanogen bromide Structure

Cyanogen bromide

1-[2-(2-imidazolyl)thiophenyliminothiocarbonyl]-4-methylpiperazine Structure

1-[2-(2-imidazo...

~%

Pentiapine Structure

N-[2-(1H-imidazol-2-ylsulfanyl)phenyl]-4-methylpiperazine-1-carboxamide Structure

N-[2-(1H-imidaz...

~%

Pentiapine Structure

methylpiperazine Structure

methylpiperazine

5-cyanothioimidazo[2,1-b][1,3,5]benzothiadiazepine Structure

5-cyanothioimid...

~%

Pentiapine Structure

1,4-Dichloro-2-nitrobenzene Structure

1,4-Dichloro-2-...

~%

5-chloro-2-(1H-imidazol-2-ylsulfanyl)aniline Structure

5-chloro-2-(1H-...

methylpiperazine Structure

methylpiperazine

imidazo[2,1-b][1,3,5]benzothiadiazepine-5(6H)-one Structure

imidazo[2,1-b][...

~98%

N-[2-(1H-imidazol-2-ylsulfanyl)phenyl]-4-methylpiperazine-1-carboxamide Structure

N-[2-(1H-imidaz...

1-Bromo-2-nitrobenzene Structure

1-Bromo-2-nitro...

~%

N-[2-(1H-imidazol-2-ylsulfanyl)phenyl]-4-methylpiperazine-1-carboxamide Structure

N-[2-(1H-imidaz...

2-(1H-imidazol-2-ylsulfanyl)aniline Structure

2-(1H-imidazol-...

~%

N-[2-(1H-imidazol-2-ylsulfanyl)phenyl]-4-methylpiperazine-1-carboxamide Structure

N-[2-(1H-imidaz...

2-(2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(2-nitropheny...

~%

N-[2-(1H-imidazol-2-ylsulfanyl)phenyl]-4-methylpiperazine-1-carboxamide Structure

N-[2-(1H-imidaz...

2-(4-fluoro-2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(4-fluoro-2-n...

~82%

5-fluoro-2-(1H-imidazol-2-ylsulfanyl)aniline Structure

5-fluoro-2-(1H-...

2,5-Difluoronitrobenzene Structure

2,5-Difluoronit...

~%

5-fluoro-2-(1H-imidazol-2-ylsulfanyl)aniline Structure

5-fluoro-2-(1H-...

2-[2-nitro-4-(trifluoromethyl)phenyl]sulfanyl-1H-imidazole Structure

2-[2-nitro-4-(t...

~85%

2-(1H-imidazol-2-ylsulfanyl)-5-(trifluoromethyl)aniline Structure

2-(1H-imidazol-...

3-Nitro-4-chlorobenzotrifluoride Structure

3-Nitro-4-chlor...

~%

2-(1H-imidazol-2-ylsulfanyl)-5-(trifluoromethyl)aniline Structure

2-(1H-imidazol-...

2-(4-methoxy-2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(4-methoxy-2-...

~92%

2-(1H-imidazol-2-ylsulfanyl)-5-methoxyaniline Structure

2-(1H-imidazol-...

4-Chloro-3-nitroanisole Structure

4-Chloro-3-nitr...

~%

2-(1H-imidazol-2-ylsulfanyl)-5-methoxyaniline Structure

2-(1H-imidazol-...

5-methyl-2-(2-nitrophenyl)sulfanyl-1H-imidazole Structure

5-methyl-2-(2-n...

~87%

2-[(5-methyl-1H-imidazol-2-yl)sulfanyl]aniline Structure

2-[(5-methyl-1H...

2-Nitrochlorobenzene Structure

2-Nitrochlorobenzene

~%

2-[(5-methyl-1H-imidazol-2-yl)sulfanyl]aniline Structure

2-[(5-methyl-1H...

2-MERCAPTOIMIDAZOLE Structure

2-MERCAPTOIMIDAZOLE

1,4-Dichloro-2-nitrobenzene Structure

1,4-Dichloro-2-...

~78%

2-(4-chloro-2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(4-chloro-2-n...

2,5-Difluoronitrobenzene Structure

2,5-Difluoronit...

2-MERCAPTOIMIDAZOLE Structure

2-MERCAPTOIMIDAZOLE

~84%

2-(4-fluoro-2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(4-fluoro-2-n...

2-MERCAPTOIMIDAZOLE Structure

2-MERCAPTOIMIDAZOLE

3-Nitro-4-chlorobenzotrifluoride Structure

3-Nitro-4-chlor...

~93%

2-[2-nitro-4-(trifluoromethyl)phenyl]sulfanyl-1H-imidazole Structure

2-[2-nitro-4-(t...

2-MERCAPTOIMIDAZOLE Structure

2-MERCAPTOIMIDAZOLE

4-Chloro-3-nitroanisole Structure

4-Chloro-3-nitr...

~69%

2-(4-methoxy-2-nitrophenyl)sulfanyl-1H-imidazole Structure

2-(4-methoxy-2-...