Structure-Activity Relationship of 2-[[(2-Pyridyl) methyl] thio]-1 H-benzimidazoles as Anti Helicobacter pylori Agents in Vitro and Evaluation of their in Vivo Efficacy

…, M Swanson, V Shcherbuchin, H Larsson…

Index: Kuehler, Thomas C.; Swanson, Marianne; Shcherbuchin, Vladimir; Larsson, Hakan; Mellgard, Bjoern; Sjoestroem, Jan-Eric Journal of Medicinal Chemistry, 1998 , vol. 41, # 11 p. 1777 - 1788

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Citation Number: 65

Abstract

A relationship between the structure of 21 2-[[(2-pyridyl) methyl] thio]-1 H-benzimidazoles (6) and their anti He l icobacter py l ori activity expressed as minimum bactericidal concentration (MBC) values is described. Observed MBCs ranged from 256 to 1 μg/mL. The structure- activity relationship (SAR) showed that larger and more lipophilic compounds, especially compounds with such substituents in the 4-position of the pyridyl moiety, generally had ...

 Related Synthetic Route
Ethanoic anhydride Structure

108-24-7

Ethanoic anhydride

4-methoxy-2,3-dimethyl-1-oxidopyridin-1-ium Structure

102625-96-7

4-methoxy-2,3-d...

~%

Acetic acid 4-methoxy-3-methyl-pyridin-2-ylmethyl ester Structure

102625-98-9

Acetic acid 4-m...

N-(4-acetyl-2-nitro-phenyl)acetamide Structure

7418-44-2

N-(4-acetyl-2-n...

~99%

4-AMINO-3-NITRO-ACETOPHENONE Structure

1432-42-4

4-AMINO-3-NITRO...

2,4-DIMETHYL-PYRIDINE 1-OXIDE Structure

1122-45-8

2,4-DIMETHYL-PY...

Ethanoic anhydride Structure

108-24-7

Ethanoic anhydride

~87%

(4-methylpyridin-2-yl)methyl acetate Structure

55485-91-1

(4-methylpyridi...

2,3,5-Trimethylpyridine N-oxide Structure

74409-42-0

2,3,5-Trimethyl...

~%

2-(ACETOXYMETHYL)-4-METHOXY-3,5-DIMETHYLPYRIDINE Structure

91219-90-8

2-(ACETOXYMETHY...

2,3,5-Trimethyl-4-nitropyridine 1-oxide Structure

86604-79-7

2,3,5-Trimethyl...

~%

2-(ACETOXYMETHYL)-4-METHOXY-3,5-DIMETHYLPYRIDINE Structure

91219-90-8

2-(ACETOXYMETHY...

2,3,5-Trimethylpyridine Structure

695-98-7

2,3,5-Trimethyl...

~%

2-(ACETOXYMETHYL)-4-METHOXY-3,5-DIMETHYLPYRIDINE Structure

91219-90-8

2-(ACETOXYMETHY...

4'-ACETAMIDOACETOPHENONE Structure

2719-21-3

4'-ACETAMIDOACE...

~57%

N-(4-acetyl-2-nitro-phenyl)acetamide Structure

7418-44-2

N-(4-acetyl-2-n...

2,3,5-Trimethylpyridine N-oxide Structure

74409-42-0

2,3,5-Trimethyl...

~%

4-Methoxy-2,3,5-trimethylpyridine N-oxide Structure

86604-80-0

4-Methoxy-2,3,5...

2,3,5-Trimethylpyridine Structure

695-98-7

2,3,5-Trimethyl...

~%

4-Methoxy-2,3,5-trimethylpyridine N-oxide Structure

86604-80-0

4-Methoxy-2,3,5...

Sodium Methylate Structure

124-41-4

Sodium Methylate

2,3,5-Trimethyl-4-nitropyridine 1-oxide Structure

86604-79-7

2,3,5-Trimethyl...

~%

4-Methoxy-2,3,5-trimethylpyridine N-oxide Structure

86604-80-0

4-Methoxy-2,3,5...

2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride Structure

86604-75-3

2-Chloromethyl-...

1H-BENZOIMIDAZOLE-2-THIOL Structure

134469-07-1

1H-BENZOIMIDAZO...

~85%

2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-1H-benzimidazole Structure

73590-87-1

2-[(4-methoxy-3...

2,3,5-Trimethylpyridine Structure

695-98-7

2,3,5-Trimethyl...

~%

2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-1H-benzimidazole Structure

73590-87-1

2-[(4-methoxy-3...

2,3,5-Trimethyl-4-nitropyridine 1-oxide Structure

86604-79-7

2,3,5-Trimethyl...

~%

2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-1H-benzimidazole Structure

73590-87-1

2-[(4-methoxy-3...

2,3,5-Trimethylpyridine N-oxide Structure

74409-42-0

2,3,5-Trimethyl...

~%

2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-1H-benzimidazole Structure

73590-87-1

2-[(4-methoxy-3...

3,5-Dimethyl-4-methoxy-2-pyridinemethanol Structure

86604-78-6

3,5-Dimethyl-4-...

~%

2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-1H-benzimidazole Structure

73590-87-1

2-[(4-methoxy-3...

4-Methoxy-2,3,5-trimethylpyridine N-oxide Structure

86604-80-0

4-Methoxy-2,3,5...

~%

2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-1H-benzimidazole Structure

73590-87-1

2-[(4-methoxy-3...

2-(ACETOXYMETHYL)-4-METHOXY-3,5-DIMETHYLPYRIDINE Structure

91219-90-8

2-(ACETOXYMETHY...

~%

2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-1H-benzimidazole Structure

73590-87-1

2-[(4-methoxy-3...

2,3-Dimethyl-4-nitropyridine 1-oxide Structure

37699-43-7

2,3-Dimethyl-4-...

~%

2-{[(4-Methoxy-3-Methyl-2-Pyridinyl)Methyl]Sulfanyl}-1H-Benzimidazole Structure

102804-82-0

2-{[(4-Methoxy-...

(4-Methoxy-3-methylpyridin-2-yl)methanol Structure

86604-77-5

(4-Methoxy-3-me...

~%

2-{[(4-Methoxy-3-Methyl-2-Pyridinyl)Methyl]Sulfanyl}-1H-Benzimidazole Structure

102804-82-0

2-{[(4-Methoxy-...

4-methoxy-2,3-dimethyl-1-oxidopyridin-1-ium Structure

102625-96-7

4-methoxy-2,3-d...

~%

2-{[(4-Methoxy-3-Methyl-2-Pyridinyl)Methyl]Sulfanyl}-1H-Benzimidazole Structure

102804-82-0

2-{[(4-Methoxy-...

Acetic acid 4-methoxy-3-methyl-pyridin-2-ylmethyl ester Structure

102625-98-9

Acetic acid 4-m...

~%

2-{[(4-Methoxy-3-Methyl-2-Pyridinyl)Methyl]Sulfanyl}-1H-Benzimidazole Structure

102804-82-0

2-{[(4-Methoxy-...

2-(Chloromethyl)-4-methoxy-3-methylpyridine Structure

124473-12-7

2-(Chloromethyl...

1H-BENZOIMIDAZOLE-2-THIOL Structure

134469-07-1

1H-BENZOIMIDAZO...

~%

2-{[(4-Methoxy-3-Methyl-2-Pyridinyl)Methyl]Sulfanyl}-1H-Benzimidazole Structure

102804-82-0

2-{[(4-Methoxy-...


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