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

[[(4, 5-Dihydro-2-oxazolyl) phenoxy] alkyl] isoxazoles. Inhibitors of picornavirus uncoating

…, MA McKinlay, MJ Otto, V Akullian…

Index: Diana; McKinlay; Otto; Akullian; Oglesby Journal of Medicinal Chemistry, 1985 , vol. 28, # 12 p. 1906 - 1910

Full Text: HTML

Citation Number: 87

Abstract

carbonyl)-3-benzothienylglycylamido]-3-methyl-3-cephem-4-carboxylate (7) was dissolved in 500 mL of dichloromethane and slurried with 20 g of silica gel 60. The solvent was removed and the mixture was added to an 8 cm X 15 cm column packed with 400 g of silica gel 60 in toluene. The column was eluted with a gradient of 2 L of 5% ethyl acetate in toluene (v/v) to 2 L of 15% ethyl acetate in toluene and finally with 3 L of 15% ethyl acetate ...

5-(8-bromooctyl)-3-methylisoxazole Structure

5-(8-bromooctyl...

4-(1,3-oxazolidin-2-ylidene)cyclohexa-2,5-dien-1-one,hydrochloride Structure

4-(1,3-oxazolid...

~53%

5-[8-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]octyl]-3-methyl-1,2-oxazole Structure

5-[8-[4-(4,5-di...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

5-[8-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]octyl]-3-methyl-1,2-oxazole Structure

5-[8-[4-(4,5-di...

1,7-Dibromoheptane Structure

1,7-Dibromoheptane

~%

5-[8-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]octyl]-3-methyl-1,2-oxazole Structure

5-[8-[4-(4,5-di...

Bryonamide A Structure

~%

5-[8-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]octyl]-3-methyl-1,2-oxazole Structure

5-[8-[4-(4,5-di...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

5-[7-[4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-(4,4-di...

1,6-Dibromohexane Structure

1,6-Dibromohexane

~%

5-[7-[4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-(4,4-di...

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

5-[7-[4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-(4,4-di...

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzonitrile Structure

ethyl 4-((7-(3-...

~%

5-[7-[4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-(4,4-di...

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzenecarboximidate hydrochloride Structure

ethyl 4-((7-(3-...

2-Amino-2-methyl-1-propanol Structure

2-Amino-2-methy...

~%

5-[7-[4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-(4,4-di...

4-(1,3-oxazolidin-2-ylidene)cyclohexa-2,5-dien-1-one,hydrochloride Structure

4-(1,3-oxazolid...

5-(4-bromobutyl)-3-methylisoxazole Structure

5-(4-bromobutyl...

~75%

5-[4-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]butyl]-3-methyl-1,2-oxazole Structure

5-[4-[4-(4,5-di...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

5-[4-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]butyl]-3-methyl-1,2-oxazole Structure

5-[4-[4-(4,5-di...

Bryonamide A Structure

~%

5-[4-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]butyl]-3-methyl-1,2-oxazole Structure

5-[4-[4-(4,5-di...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-5-yl]methanol Structure

[2-[4-[7-(3-met...

1,6-Dibromohexane Structure

1,6-Dibromohexane

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-5-yl]methanol Structure

[2-[4-[7-(3-met...

4-(6-bromohexoxy)benzonitrile Structure

4-(6-bromohexox...

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-5-yl]methanol Structure

[2-[4-[7-(3-met...

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-5-yl]methanol Structure

[2-[4-[7-(3-met...

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzonitrile Structure

ethyl 4-((7-(3-...

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-5-yl]methanol Structure

[2-[4-[7-(3-met...

3-Amino-1,2-propanediol Structure

3-Amino-1,2-pro...

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzenecarboximidate hydrochloride Structure

ethyl 4-((7-(3-...

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-5-yl]methanol Structure

[2-[4-[7-(3-met...

4-(6-bromohexoxy)benzonitrile Structure

4-(6-bromohexox...

~%

5-[7-[4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-(4,4-di...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-4-yl]methanol Structure

[2-[4-[7-(3-met...

1,6-Dibromohexane Structure

1,6-Dibromohexane

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-4-yl]methanol Structure

[2-[4-[7-(3-met...

4-(6-bromohexoxy)benzonitrile Structure

4-(6-bromohexox...

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-4-yl]methanol Structure

[2-[4-[7-(3-met...

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-4-yl]methanol Structure

[2-[4-[7-(3-met...

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzonitrile Structure

ethyl 4-((7-(3-...

~%

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-4-yl]methanol Structure

[2-[4-[7-(3-met...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

5-[5-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl]-3-methyl-1,2-oxazole Structure

5-[5-[4-(4,5-di...

Bryonamide A Structure

~94%

4-(1,3-oxazolidin-2-ylidene)cyclohexa-2,5-dien-1-one,hydrochloride Structure

4-(1,3-oxazolid...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

3-methyl-5-[7-[4-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenoxy]heptyl]-1,2-oxazole Structure

3-methyl-5-[7-[...

1,6-Dibromohexane Structure

1,6-Dibromohexane

~%

3-methyl-5-[7-[4-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenoxy]heptyl]-1,2-oxazole Structure

3-methyl-5-[7-[...

4-(6-bromohexoxy)benzonitrile Structure

4-(6-bromohexox...

~%

3-methyl-5-[7-[4-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenoxy]heptyl]-1,2-oxazole Structure

3-methyl-5-[7-[...

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

3-methyl-5-[7-[4-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenoxy]heptyl]-1,2-oxazole Structure

3-methyl-5-[7-[...

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzonitrile Structure

ethyl 4-((7-(3-...

~%

3-methyl-5-[7-[4-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenoxy]heptyl]-1,2-oxazole Structure

3-methyl-5-[7-[...

DL-Alaninol Structure

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzenecarboximidate hydrochloride Structure

ethyl 4-((7-(3-...

~%

3-methyl-5-[7-[4-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenoxy]heptyl]-1,2-oxazole Structure

3-methyl-5-[7-[...

[2-[4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]phenyl]-4,5-dihydro-1,3-oxazol-5-yl]methanol Structure

[2-[4-[7-(3-met...

methyl iodide Structure

~%

5-[7-[4-[5-(methoxymethyl)-4,5-dihydro-1,3-oxazol-2-yl]phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-[5-(met...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

5-[7-[4-[5-(methoxymethyl)-4,5-dihydro-1,3-oxazol-2-yl]phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-[5-(met...

1,6-Dibromohexane Structure

1,6-Dibromohexane

~%

5-[7-[4-[5-(methoxymethyl)-4,5-dihydro-1,3-oxazol-2-yl]phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-[5-(met...

4-(6-bromohexoxy)benzonitrile Structure

4-(6-bromohexox...

~%

5-[7-[4-[5-(methoxymethyl)-4,5-dihydro-1,3-oxazol-2-yl]phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-[5-(met...

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

5-[7-[4-[5-(methoxymethyl)-4,5-dihydro-1,3-oxazol-2-yl]phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-[5-(met...

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzonitrile Structure

ethyl 4-((7-(3-...

~%

5-[7-[4-[5-(methoxymethyl)-4,5-dihydro-1,3-oxazol-2-yl]phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-[5-(met...

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzenecarboximidate hydrochloride Structure

ethyl 4-((7-(3-...

~%

5-[7-[4-[5-(methoxymethyl)-4,5-dihydro-1,3-oxazol-2-yl]phenoxy]heptyl]-3-methyl-1,2-oxazole Structure

5-[7-[4-[5-(met...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

Disoxaril Structure

1,6-Dibromohexane Structure

1,6-Dibromohexane

~%

Disoxaril Structure

4-(6-bromohexoxy)benzonitrile Structure

4-(6-bromohexox...

~%

Disoxaril Structure

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~%

Disoxaril Structure

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzonitrile Structure

ethyl 4-((7-(3-...

~%

Disoxaril Structure

ethyl 4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)benzenecarboximidate hydrochloride Structure

ethyl 4-((7-(3-...

2-Aminoethanol Structure

~%

Disoxaril Structure

4-(1,3-oxazolidin-2-ylidene)cyclohexa-2,5-dien-1-one,hydrochloride Structure

4-(1,3-oxazolid...

N/A Structure

~73%

5-[6-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]hexyl]-3-methyl-1,2-oxazole Structure

5-[6-[4-(4,5-di...

3,5-Dimethylisoxazole Structure

3,5-Dimethyliso...

~%

5-[6-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]hexyl]-3-methyl-1,2-oxazole Structure

5-[6-[4-(4,5-di...

1,5-Dibromopentane Structure

1,5-Dibromopentane

~%

5-[6-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]hexyl]-3-methyl-1,2-oxazole Structure

5-[6-[4-(4,5-di...

Bryonamide A Structure

~%

5-[6-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]hexyl]-3-methyl-1,2-oxazole Structure

5-[6-[4-(4,5-di...