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

Synthesis of 2-(2, 3-dihydro-2-oxo-1, 3, 4-oxadiazol-5-yl) benzo heterocycles. A novel series of orally active antiallergic agents

…, RE Brown, B Loev, K Bailey, H Jones…

Index: Musser, John H.; Brown, Richard E.; Loev, Bernard; Bailey, Kevin; Jones, Howard; et al. Journal of Medicinal Chemistry, 1984 , vol. 27, # 2 p. 121 - 125

Full Text: HTML

Citation Number: 66

Abstract

A series of new 2-(2, 3-dihydro-2-oxo-1, 3, 4-oxadiazol-5-y1) benzo heterocycles has been prepared. These compounds were tested as inhibitors of antigen-induced release of histamine (AIR) in vitro from rat peritoneal mast cells (RMC) and as inhibitors of IgE- mediated rat passive cutaneous anaphylaxis in the rat (PCA). Most of this new class of antiallergic agents showed good activity in the RMC assay. The most potent compound, 3- ...

ethyl 2-(5-chlorobenzo[d]oxazole-2-carbonyl)hydrazine-1-carboxylate Structure

ethyl 2-(5-chlo...

~%

5-(5-chloro-1,3-benzoxazol-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(5-chloro-1,3...

ethyl 2-(6-methylbenzo[d]oxazole-2-carbonyl)hydrazine-1-carboxylate Structure

ethyl 2-(6-meth...

~%

5-(6-methyl-1,3-benzoxazol-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(6-methyl-1,3...

3-chloro-7-methyl-1,4-benzoxazin-2-one Structure

3-chloro-7-meth...

~%

5-(6-methyl-1,3-benzoxazol-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(6-methyl-1,3...

ethyl 2-(4-methylbenzo[d]oxazole-2-carbonyl)hydrazine-1-carboxylate Structure

ethyl 2-(4-meth...

~%

5-(4-methyl-1,3-benzoxazol-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(4-methyl-1,3...

3-chloro-5-methyl-1,4-benzoxazin-2-one Structure

3-chloro-5-meth...

~%

5-(4-methyl-1,3-benzoxazol-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(4-methyl-1,3...

methyl 1,5-dimethylbenzimidazole-2-carboxylate Structure

methyl 1,5-dime...

~%

1,5-dimethylbenzimidazole-2-carbohydrazide Structure

1,5-dimethylben...

methyl 3-methyl-1H-indene-2-carboxylate Structure

methyl 3-methyl...

~%

3-methyl-1H-indene-2-carbohydrazide Structure

3-methyl-1H-ind...

methyl 5-methylbenzo[d]oxazole-2-carboxylate Structure

methyl 5-methyl...

~%

5-(5-methyl-1,3-benzoxazol-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(5-methyl-1,3...

Ethanoic anhydride Structure

Ethanoic anhydride

2-(2,3-dihydro-1,3,4-oxadiazol-5-yl)benzoxazole Structure

2-(2,3-dihydro-...

~62%

3-acetyl-5-(1,3-benzoxazol-2-yl)-1,3,4-oxadiazol-2-one Structure

3-acetyl-5-(1,3...

3-CHLORO-2H-BENZO[B][1,4]OXAZIN-2-ONE Structure

3-CHLORO-2H-BEN...

~%

3-acetyl-5-(1,3-benzoxazol-2-yl)-1,3,4-oxadiazol-2-one Structure

3-acetyl-5-(1,3...

ethyl 3-(2-benzoxazolyl)hydrazinecarboxylate Structure

ethyl 3-(2-benz...

~%

3-acetyl-5-(1,3-benzoxazol-2-yl)-1,3,4-oxadiazol-2-one Structure

3-acetyl-5-(1,3...

METHYL BENZO[D]OXAZOLE-2-CARBOXYLATE Structure

METHYL BENZO[D]...

~%

3-acetyl-5-(1,3-benzoxazol-2-yl)-1,3,4-oxadiazol-2-one Structure

3-acetyl-5-(1,3...

3-CHLORO-2H-BENZO[B][1,4]OXAZIN-2-ONE Structure

3-CHLORO-2H-BEN...

~%

5-(1,3-benzoxazol-2-yl)-3-methyl-1,3,4-oxadiazol-2-one Structure

5-(1,3-benzoxaz...

ethyl 3-(2-benzoxazolyl)hydrazinecarboxylate Structure

ethyl 3-(2-benz...

~%

5-(1,3-benzoxazol-2-yl)-3-methyl-1,3,4-oxadiazol-2-one Structure

5-(1,3-benzoxaz...

METHYL BENZO[D]OXAZOLE-2-CARBOXYLATE Structure

METHYL BENZO[D]...

~%

5-(1,3-benzoxazol-2-yl)-3-methyl-1,3,4-oxadiazol-2-one Structure

5-(1,3-benzoxaz...

2-(2,3-dihydro-1,3,4-oxadiazol-5-yl)benzoxazole Structure

2-(2,3-dihydro-...

~%

5-(1,3-benzoxazol-2-yl)-3-methyl-1,3,4-oxadiazol-2-one Structure

5-(1,3-benzoxaz...

1-methyl-2-(trichloromethyl)benzimidazole Structure

1-methyl-2-(tri...

~%

3-acetyl-5-(1-methylbenzimidazol-2-yl)-1,3,4-oxadiazol-2-one Structure

3-acetyl-5-(1-m...

Ethanoic anhydride Structure

Ethanoic anhydride

ethyl 3-(1-methyl-2-benzimidazolyl)hydrazinecarboxylate Structure

ethyl 3-(1-meth...

~%

3-acetyl-5-(1-methylbenzimidazol-2-yl)-1,3,4-oxadiazol-2-one Structure

3-acetyl-5-(1-m...

METHYL 1-METHYL-1H-BENZO[D]IMIDAZOLE-2-CARBOXYLATE Structure

METHYL 1-METHYL...

~91%

1H-Benzimidazole-2-carboxylicacid,1-methyl-,hydrazide(9CI) Structure

1H-Benzimidazol...

methyl 1,5-dimethylbenzimidazole-2-carboxylate Structure

methyl 1,5-dime...

~%

5-(1,5-dimethylbenzimidazol-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(1,5-dimethyl...

phosgene Structure

1,5-dimethylbenzimidazole-2-carbohydrazide Structure

1,5-dimethylben...

~%

5-(1,5-dimethylbenzimidazol-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(1,5-dimethyl...

methyl 3-methyl-1H-indene-2-carboxylate Structure

methyl 3-methyl...

~%

5-(3-methyl-1H-inden-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(3-methyl-1H-...

phosgene Structure

3-methyl-1H-indene-2-carbohydrazide Structure

3-methyl-1H-ind...

~%

5-(3-methyl-1H-inden-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(3-methyl-1H-...

1-methyl-2-(trichloromethyl)benzimidazole Structure

1-methyl-2-(tri...

~%

1H-Benzimidazole-2-carboxylicacid,1-methyl-,hydrazide(9CI) Structure

1H-Benzimidazol...

ethyl 3-(1-methyl-2-benzimidazolyl)hydrazinecarboxylate Structure

ethyl 3-(1-meth...

~85%

5-(1-benzofuran-2-yl)-3H-1,3,4-oxadiazol-2-one Structure

5-(1-benzofuran...

Methanol Structure

1-methyl-2-(trichloromethyl)benzimidazole Structure

1-methyl-2-(tri...

~60%

METHYL 1-METHYL-1H-BENZO[D]IMIDAZOLE-2-CARBOXYLATE Structure

METHYL 1-METHYL...

benzofuran-2-carbonyl chloride Structure

benzofuran-2-ca...

Ethyl hydrazinecarboxylate Structure

Ethyl hydrazine...

~58%

ethyl N-(1-benzofuran-2-carbonylamino)carbamate Structure

ethyl N-(1-benz...