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

N??(4??Biphenylmethyl) imidazoles as Potential Therapeutics for the Treatment of Prostate Cancer: Metabolic Robustness Due to Fluorine Substitution?

F Leroux, TU Hutschenreuter, C Charrière…

Index: Leroux, Frederic; Hutschenreuter, Tilman U.; Charriere, Celine; Scopelliti, Rosario; Hartmann, Rolf W. Helvetica Chimica Acta, 2003 , vol. 86, # 7 p. 2671 - 2686

Full Text: HTML

Citation Number: 44

Abstract

Abstract 3, 3′, 5, 5′-And 2, 2′, 6, 6′-tetrafluoro-substituted 1-[(1, 1′-biphenyl]-4-yl) methyl]-1H-imidazoles were synthesized as inhibitors of 17α-hydroxylase-C17, 20-lyase (P450 17, CYP 17). P450 17 is the key enzyme of androgen biosynthesis. Its inhibition is a novel therapeutic approach for treatment of prostate cancer. To increase the so-far insufficient in vivo lifetime of such compounds, the metabolically sensitive positions were ...

4'-Bromo-[1,1'-biphenyl]-4-carboxaldehyde Structure

4'-Bromo-[1,1'-...

~96%

[4-(4-bromophenyl)phenyl]methanol Structure

[4-(4-bromophen...

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4,4'-Dibromobiphenyl Structure

4,4'-Dibromobiphenyl

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~89%

4'-Bromo-[1,1'-biphenyl]-4-carboxaldehyde Structure

4'-Bromo-[1,1'-...

4,4'-Biphenyldicarbaldehyde Structure

4,4'-Biphenyldi...

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2,2',6,6'-tetrafluoro-4'-methoxy[1,1'-biphenyl]-4-methanol Structure

2,2',6,6'-tetra...

~82%

2-(bromomethyl)-5-(3,5-difluoro-4-methoxyphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

2-(bromomethyl)-5-(3,5-difluoro-4-methoxyphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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1-(3,5-difluorophenyl)-3,5-difluorobenzene Structure

1-(3,5-difluoro...

~%

2-(bromomethyl)-5-(3,5-difluoro-4-methoxyphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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5-(3,5-difluorophenyl)-1,3-difluoro-2-methylbenzene Structure

5-(3,5-difluoro...

~%

2-(bromomethyl)-5-(3,5-difluoro-4-methoxyphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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5-(3,5-difluorophenyl)-1,3-difluoro-2-methoxybenzene Structure

5-(3,5-difluoro...

~%

2-(bromomethyl)-5-(3,5-difluoro-4-methoxyphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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3,3',5,5'-tetrafluoro-4'-methoxy[1,1'-biphenyl]-4-carbaldehyde Structure

3,3',5,5'-tetra...

~%

2-(bromomethyl)-5-(3,5-difluoro-4-methoxyphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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5-Bromo-1,3-difluoro-2-iodobenzene Structure

5-Bromo-1,3-dif...

~76%

5-bromo-2-(4-bromo-2,6-difluorophenyl)-1,3-difluorobenzene Structure

5-bromo-2-(4-br...

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1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

5-bromo-2-(4-bromo-2,6-difluorophenyl)-1,3-difluorobenzene Structure

5-bromo-2-(4-br...

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5-bromo-2-(4-bromo-2,6-difluorophenyl)-1,3-difluorobenzene Structure

5-bromo-2-(4-br...

~%

2-(4-bromo-2,6-difluorophenyl)-5-(bromomethyl)-1,3-difluorobenzene Structure

2-(4-bromo-2,6-...

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4'-bromo-2,2',6,6'-tetrafluoro-[1,1'-biphenyl]-4-carbaldehyde Structure

4'-bromo-2,2',6...

~%

2-(4-bromo-2,6-difluorophenyl)-5-(bromomethyl)-1,3-difluorobenzene Structure

2-(4-bromo-2,6-...

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4'-bromo-2,2',6,6'-tetrafluoro[1,1'-biphenyl]-4-methanol Structure

4'-bromo-2,2',6...

~80%

2-(4-bromo-2,6-difluorophenyl)-5-(bromomethyl)-1,3-difluorobenzene Structure

2-(4-bromo-2,6-...

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1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

2-(4-bromo-2,6-difluorophenyl)-5-(bromomethyl)-1,3-difluorobenzene Structure

2-(4-bromo-2,6-...

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5-Bromo-1,3-difluoro-2-iodobenzene Structure

5-Bromo-1,3-dif...

~%

2-(4-bromo-2,6-difluorophenyl)-5-(bromomethyl)-1,3-difluorobenzene Structure

2-(4-bromo-2,6-...

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N/A Structure

~79%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methylbenzene Structure

2-[4-(bromometh...

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1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methylbenzene Structure

2-[4-(bromometh...

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5-Bromo-1,3-difluoro-2-iodobenzene Structure

5-Bromo-1,3-dif...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methylbenzene Structure

2-[4-(bromometh...

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5-bromo-2-(4-bromo-2,6-difluorophenyl)-1,3-difluorobenzene Structure

5-bromo-2-(4-br...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methylbenzene Structure

2-[4-(bromometh...

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4'-bromo-2,2',6,6'-tetrafluoro-[1,1'-biphenyl]-4-carbaldehyde Structure

4'-bromo-2,2',6...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methylbenzene Structure

2-[4-(bromometh...

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4'-bromo-2,2',6,6'-tetrafluoro[1,1'-biphenyl]-4-methanol Structure

4'-bromo-2,2',6...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methylbenzene Structure

2-[4-(bromometh...

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4-bromo-2,2',6,6'-tetrafluoro-4'-{[(triisopropylsilyl)oxy]methyl}[1,1'-biphenyl] Structure

4-bromo-2,2',6,...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methylbenzene Structure

2-[4-(bromometh...

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2,2',6,6'-tetrafluoro-4-methyl-4'-{[(triisopropylsilyl)oxy]methyl}[1,1'-biphenyl] Structure

2,2',6,6'-tetra...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methylbenzene Structure

2-[4-(bromometh...

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(2,2',6,6'-tetrafluoro-4'-methoxy-[1,1'-biphenyl]-4-yl)methanol Structure

(2,2',6,6'-tetr...

~78%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methoxybenzene Structure

2-[4-(bromometh...

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1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methoxybenzene Structure

2-[4-(bromometh...

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5-Bromo-1,3-difluoro-2-iodobenzene Structure

5-Bromo-1,3-dif...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methoxybenzene Structure

2-[4-(bromometh...

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5-bromo-2-(4-bromo-2,6-difluorophenyl)-1,3-difluorobenzene Structure

5-bromo-2-(4-br...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methoxybenzene Structure

2-[4-(bromometh...

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4'-bromo-2,2',6,6'-tetrafluoro-[1,1'-biphenyl]-4-carbaldehyde Structure

4'-bromo-2,2',6...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methoxybenzene Structure

2-[4-(bromometh...

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4'-bromo-2,2',6,6'-tetrafluoro[1,1'-biphenyl]-4-methanol Structure

4'-bromo-2,2',6...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methoxybenzene Structure

2-[4-(bromometh...

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2,2',6,6'-tetrafluoro-4-methoxy-4'-{[(triisopropylsilyl)oxy]methyl}[1,1'-biphenyl] Structure

2,2',6,6'-tetra...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methoxybenzene Structure

2-[4-(bromometh...

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4-bromo-2,2',6,6'-tetrafluoro-4'-{[(triisopropylsilyl)oxy]methyl}[1,1'-biphenyl] Structure

4-bromo-2,2',6,...

~%

2-[4-(bromomethyl)-2,6-difluorophenyl]-1,3-difluoro-5-methoxybenzene Structure

2-[4-(bromometh...

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4,4'-Dibromobiphenyl Structure

4,4'-Dibromobiphenyl

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~0%

4'-Bromo-[1,1'-biphenyl]-4-carboxaldehyde Structure

4'-Bromo-[1,1'-...

4,4'-Biphenyldicarbaldehyde Structure

4,4'-Biphenyldi...

Learn More

1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~85%

1-(3,5-difluorophenyl)-3,5-difluorobenzene Structure

1-(3,5-difluoro...

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1-(3,5-difluorophenyl)-3,5-difluorobenzene Structure

1-(3,5-difluoro...

Dimethyl sulfate Structure

Dimethyl sulfate

~81%

5-(3,5-difluorophenyl)-1,3-difluoro-2-methylbenzene Structure

5-(3,5-difluoro...

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1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

5-(3,5-difluorophenyl)-1,3-difluoro-2-methylbenzene Structure

5-(3,5-difluoro...

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1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

5-(3,5-difluorophenyl)-1,3-difluoro-2-methoxybenzene Structure

5-(3,5-difluoro...

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1-(3,5-difluorophenyl)-3,5-difluorobenzene Structure

1-(3,5-difluoro...

~%

5-(3,5-difluorophenyl)-1,3-difluoro-2-methoxybenzene Structure

5-(3,5-difluoro...

Learn More

1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~82%

5-Bromo-1,3-difluoro-2-iodobenzene Structure

5-Bromo-1,3-dif...

Learn More

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

5-(3,5-difluorophenyl)-1,3-difluoro-2-methylbenzene Structure

5-(3,5-difluoro...

~80%

4-(3,5-difluoro-4-methylphenyl)-2,6-difluorobenzaldehyde Structure

4-(3,5-difluoro...

Learn More

1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

4-(3,5-difluoro-4-methylphenyl)-2,6-difluorobenzaldehyde Structure

4-(3,5-difluoro...

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1-(3,5-difluorophenyl)-3,5-difluorobenzene Structure

1-(3,5-difluoro...

~%

4-(3,5-difluoro-4-methylphenyl)-2,6-difluorobenzaldehyde Structure

4-(3,5-difluoro...

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N/A Structure

~88%

2-(bromomethyl)-5-(3,5-difluorophenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

2-(bromomethyl)-5-(3,5-difluorophenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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1-(3,5-difluorophenyl)-3,5-difluorobenzene Structure

1-(3,5-difluoro...

~%

2-(bromomethyl)-5-(3,5-difluorophenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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N/A Structure

~%

2-(bromomethyl)-5-(3,5-difluorophenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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3,3',5,5'-tetrafluoro-4'-methyl[1,1'-biphenyl]-4-methanol Structure

3,3',5,5'-tetra...

~90%

2-(bromomethyl)-5-(3,5-difluoro-4-methylphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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1-Bromo-3,5-difluorobenzene Structure

1-Bromo-3,5-dif...

~%

2-(bromomethyl)-5-(3,5-difluoro-4-methylphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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1-(3,5-difluorophenyl)-3,5-difluorobenzene Structure

1-(3,5-difluoro...

~%

2-(bromomethyl)-5-(3,5-difluoro-4-methylphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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5-(3,5-difluorophenyl)-1,3-difluoro-2-methylbenzene Structure

5-(3,5-difluoro...

~%

2-(bromomethyl)-5-(3,5-difluoro-4-methylphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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4-(3,5-difluoro-4-methylphenyl)-2,6-difluorobenzaldehyde Structure

4-(3,5-difluoro...

~%

2-(bromomethyl)-5-(3,5-difluoro-4-methylphenyl)-1,3-difluorobenzene Structure

2-(bromomethyl)...

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Conformationally restricted retinoids

[Journal of Medicinal Chemistry, , vol. 27, # 11 p. 1516 - 1531]

Conformationally restricted retinoids

[Journal of Medicinal Chemistry, , vol. 27, # 11 p. 1516 - 1531]

Silicon directed ipso-substitution of polymer bound arylsila...

[Tetrahedron Letters, , vol. 37, # 16 p. 2703 - 2706]

Silicon directed ipso-substitution of polymer bound arylsila...

[Tetrahedron Letters, , vol. 37, # 16 p. 2703 - 2706]

Silicon directed ipso-substitution of polymer bound arylsila...

[Tetrahedron Letters, , vol. 37, # 16 p. 2703 - 2706]