Structure-activity studies of 5-[[4-(4, 5-dihydro-2-oxazolyl) phenoxy] alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating

…, V Akullian, PM Carabateas, D Cutcliffe…

Index: Diana, Guy D.; Oglesby, Richard C.; Akullian, Vahan; Carabateas, Phillip M.; Cutcliffe, David; et al. Journal of Medicinal Chemistry, 1987 , vol. 30, # 2 p. 383 - 388

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Citation Number: 35

Abstract

The mode of action of compound 1 has been shown to be the inhibition of viral uncoating. 6 The role of uncoating in the replication of picornaviruses is graphically shown in Figure 1. After receptor-mediated adsorption of the virus to the cell membrane, the virion penetrates ...

 Related Synthetic Route
5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

Phenol, 4-(4,5-dihydro-2-oxazolyl)-3-methyl Structure

98033-59-1

Phenol, 4-(4,5-...

~55%

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

105639-03-0

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

ethyl 4-hydroxy-2-methylbenzoate Structure

57081-00-2

ethyl 4-hydroxy...

~%

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

105639-03-0

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

5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

4-(4,5-dihydrooxazol-2-yl)-2-ethylphenol hydrochloride Structure

105639-21-2

4-(4,5-dihydroo...

~65%

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

105639-07-4

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

5-(4,5-dihydro-1,3-oxazol-2-yl)-2-[5-(3-methyl-1,2-oxazol-5-yl)pentoxy]benzaldehyde Structure

105639-13-2

5-(4,5-dihydro-...

~27%

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

105639-15-4

5-[5-[2-(difluo...

5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

~%

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

105639-15-4

5-[5-[2-(difluo...

4-(4,5-dihydro-2-oxazolyl)-2-formylphenol,hydrochloride salt Structure

105639-26-7

4-(4,5-dihydro-...

~%

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

105639-15-4

5-[5-[2-(difluo...

3-chloro-4-(4,5-dihydro-2-oxazoyl)phenol hydrochloride Structure

98033-81-9

3-chloro-4-(4,5...

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

98033-94-4

5-(4-bromobutyl...

~71%

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

98033-98-8

5-[4-[2-chloro-...

Ethyl 3-chloro-4-hydroxybenzoate Structure

16357-41-8

Ethyl 3-chloro-...

~%

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

98033-98-8

5-[4-[2-chloro-...

N/A Structure

98033-80-8

N/A

~%

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

98033-98-8

5-[4-[2-chloro-...

Phenol, 4-(4,5-dihydro-2-oxazolyl)- Structure

81428-58-2

Phenol, 4-(4,5-...

5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

~71%

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

98034-30-1

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

5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

4-(4,5-dihydrooxazol-2-yl)-2-nitrophenol hydrochloride Structure

105639-24-5

4-(4,5-dihydroo...

~24%

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

105639-10-9

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

ethyl 4-hydroxy-3-nitrobenzoate Structure

19013-10-6

ethyl 4-hydroxy...

~%

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

105639-10-9

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

Phenol, 4-(4,5-dihydro-2-oxazolyl)- Structure

81428-58-2

Phenol, 4-(4,5-...

7-(3-methylisoxazol-5-yl)heptyl bromide Structure

91945-38-9

7-(3-methylisox...

~76%

Disoxaril Structure

87495-31-6

Disoxaril

5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

2-bromo-4-(4,5-dihydro-2-oxazolyl)phenol Structure

105639-19-8

2-bromo-4-(4,5-...

~42%

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

105639-04-1

5-[5-[2-bromo-4...

3-BROMO-2-CHLORO-5-PICOLINE Structure

37470-58-9

3-BROMO-2-CHLOR...

~%

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

105639-04-1

5-[5-[2-bromo-4...

5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

4-(4,5-dihydro-2-oxazolyl)-2-formylphenol,hydrochloride salt Structure

105639-26-7

4-(4,5-dihydro-...

~71%

5-(4,5-dihydro-1,3-oxazol-2-yl)-2-[5-(3-methyl-1,2-oxazol-5-yl)pentoxy]benzaldehyde Structure

105639-13-2

5-(4,5-dihydro-...

5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

N/A Structure

98033-64-8

N/A

~45%

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

98033-66-0

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

Ethyl vanillate Structure

617-05-0

Ethyl vanillate

~%

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

98033-66-0

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

bryonamide B Structure

5942-25-6

bryonamide B

~%

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

98033-66-0

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

3-chloro-4-(4,5-dihydro-2-oxazoyl)phenol hydrochloride Structure

98033-81-9

3-chloro-4-(4,5...

7-(3-methylisoxazol-5-yl)heptyl bromide Structure

91945-38-9

7-(3-methylisox...

~73%

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

98033-82-0

5-[7-[2-chloro-...

Ethyl 3-chloro-4-hydroxybenzoate Structure

16357-41-8

Ethyl 3-chloro-...

~%

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

98033-82-0

5-[7-[2-chloro-...

N/A Structure

98033-80-8

N/A

~%

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

98033-82-0

5-[7-[2-chloro-...

3-chloro-4-(4,5-dihydro-2-oxazoyl)phenol hydrochloride Structure

98033-81-9

3-chloro-4-(4,5...

N/A Structure

98033-83-1

N/A

~53%

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

98033-87-5

5-[6-[2-chloro-...

Ethyl 3-chloro-4-hydroxybenzoate Structure

16357-41-8

Ethyl 3-chloro-...

~%

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

98033-87-5

5-[6-[2-chloro-...

N/A Structure

98033-80-8

N/A

~%

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

98033-87-5

5-[6-[2-chloro-...

5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

4-(1,3-oxazolidin-2-ylidene)-2-propan-2-ylcyclohexa-2,5-dien-1-one Structure

105639-22-3

4-(1,3-oxazolid...

~24%

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

105639-08-5

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

5-(5-bromopentyl)-3-methylisoxazole Structure

98033-85-3

5-(5-bromopenty...

4-(4,5-dihydro-2-oxazolyl)-2-(dimethylamino)phenol Structure

105639-27-8

4-(4,5-dihydro-...

~18%

5-(4,5-dihydro-1,3-oxazol-2-yl)-N,N-dimethyl-2-[5-(3-methyl-1,2-oxazol-5-yl)pentoxy]aniline Structure

105639-18-7

5-(4,5-dihydro-...


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