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

Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

D Conole, TM Beck, M Jay-Smith, MD Tingle…

Index: Conole, Daniel; Beck, Thorsten M.; Jay-Smith, Morgan; Tingle, Malcolm D.; Eason, Charles T.; Brimble, Margaret A.; Rennison, David Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 7 p. 2220 - 2235

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Citation Number: 9

Abstract

Abstract A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia— with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1, 2, 4-oxadiazole 3 (metHb%= 61.0±3.6) and 1, 3, 4-oxadiazole 10 (metHb% ...

3-phenyl-5-(4'-nitrophenyl)-1,2,4-oxadiazole Structure

3-phenyl-5-(4'-...

~82%

4-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline Structure

4-(3-phenyl-1,2...

N-Hydroxybenzenecarboximidamide Structure

N-Hydroxybenzen...

~%

4-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline Structure

4-(3-phenyl-1,2...

Benzonitrile Structure

~%

4-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline Structure

4-(3-phenyl-1,2...

Benzoyl chloride Structure

Benzoyl chloride

4-nitrobenzhydrazide Structure

4-nitrobenzhydrazide

~76%

Benzoic acid, 4-nitro-,2-benzoylhydrazide Structure

Benzoic acid, 4...

4'-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE Structure

4'-(4,4,5,5-TET...

~%

4-(4-AMINOPHENYL)PYRIMIDINE Structure

4-(4-AMINOPHENY...

N-(4-(6-chloropyrimidin-4-yl)phenyl)acetamide Structure

N-(4-(6-chlorop...

~%

4-(4-AMINOPHENYL)PYRIMIDINE Structure

4-(4-AMINOPHENY...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

2-Methyl-5-(4-nitrophenyl)-1,3,4-oxadiazole Structure

2-Methyl-5-(4-n...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

4-NITROBENZOTHIOAMIDE Structure

4-NITROBENZOTHI...

4'-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE Structure

4'-(4,4,5,5-TET...

~%

Benzenamine, 4-(5-pyrimidinyl)- (9CI) Structure

Benzenamine, 4-...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

2-(4-nitrophenyl)-5-phenyl-[1,3,4]oxadiazole Structure

2-(4-nitropheny...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~56%

4-nitrobenzhydrazide Structure

4-nitrobenzhydrazide

Butanoic anhydride Structure

Butanoic anhydride

4-Nitroaniline Structure

~80%

N-(4-nitrophenyl)butanamide Structure

N-(4-nitropheny...

N-(4-(pyridin-4-yl)phenyl)acetamide Structure

N-(4-(pyridin-4...

~91%

4-(Pyridin-4-yl)aniline Structure

4-(Pyridin-4-yl...

2-Methyl-5-(4-nitrophenyl)-1,3,4-oxadiazole Structure

2-Methyl-5-(4-n...

~53%

4-(5-Methyl-1,3,4-oxadiazol-2-yl)aniline Structure

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

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

4-(5-Methyl-1,3,4-oxadiazol-2-yl)aniline Structure

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

4-nitrobenzhydrazide Structure

4-nitrobenzhydrazide

~%

4-(5-Methyl-1,3,4-oxadiazol-2-yl)aniline Structure

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

1-Acetyl-2-(4-nitrobenzoyl)hydrazine Structure

1-Acetyl-2-(4-n...

~%

4-(5-Methyl-1,3,4-oxadiazol-2-yl)aniline Structure

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

4-nitrobenzhydrazide Structure

4-nitrobenzhydrazide

Acetyl chloride Structure

Acetyl chloride

~30%

1-Acetyl-2-(4-nitrobenzoyl)hydrazine Structure

1-Acetyl-2-(4-n...

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

~%

1-Acetyl-2-(4-nitrobenzoyl)hydrazine Structure

1-Acetyl-2-(4-n...