185563-94-4

Basic information

• Product Name: 3-Isoxazolecarboxylic acid, 4,5-dihydro-5-[4-[[1-(triphenylmethyl)-1H-imidazol-2-yl]amino]butyl]-, ethyl ester
• CAS NO: 185563-94-4
• Molecular Formula: C32H34N4O3
• Molecular Weight: 522.647
• Mol File: 185563-94-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-Isoxazolecarboxylic acid, 4,5-dihydro-5-[4-[[1-(triphenylmethyl)-1H-imidazol-2-yl]amino]butyl]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isoxazolecarboxylic acid, 4,5-dihydro-5-[4-[[1-(triphenylmethyl)-1H-imidazol-2-yl]amino]butyl]-, ethyl ester(185563-94-4)
• EPA Substance Registry System: 3-Isoxazolecarboxylic acid, 4,5-dihydro-5-[4-[[1-(triphenylmethyl)-1H-imidazol-2-yl]amino]butyl]-, ethyl ester(185563-94-4)

Safety Data

• Hazardous Substances Data: 185563-94-4(Hazardous Substances Data)

Usage

Structural Components

Carboxylic acid group
Isoxazole ring
Imidazole group
Ethyl ester moiety

Potential Pharmacological Properties

Potential biological activity due to the presence of imidazole and isoxazole groups
Likely to act as a ligand for biological receptors or enzymes

Medicinal Chemistry Research

May be utilized in medicinal chemistry research
Possible applications in drug discovery and development

Physicochemical Characteristics

Increased lipophilicity due to the ethyl ester group
Enhanced ability to penetrate biological membranes

Overall Significance

Valuable tool for drug discovery and development

Upstream product

• 821-41-0 5-Hexen-1-ol 
• 185563-93-3 1-(triphenylmethyl)imidazole-2-ylamine 
• 185563-92-2 1Triphenylmethyl-2-phthalimidoimidazole 
• 185563-78-4 ethyl 5-(4-oxobutyl)isoxazoline-3-carboxylate 
• 185563-77-3 3-ethoxycarbonyl-5-(4-hydroxybutyl)isoxazoline 

Downstream Products

• 185563-95-5 5-[4-(1-triphenylmethylimidazol-2-ylamino)butyl]isoxazoline-3-carboxylic acid 
• 258845-39-5 2-(3,5-dichloro-biphenyl-4-sulfonylamino)-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid 
• 258845-40-8 2-(3,5-dimethyl-biphenyl-4-sulfonylamino)-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid 
• 185563-99-9 2-(2,4,6-trimethyl-benzenesulfonylamino)-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid tert-butyl ester 
• 258845-37-3 2-(2,6-dichloro-benzenesulfonylamino)-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid 
• 185564-00-5 2-(2,4,6-trimethyl-benzenesulfonylamino)-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid 
• 258845-44-2 2-(biphenyl-4-sulfonylamino)-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid 
• 258845-42-0 2-(naphthalene-1-sulfonylamino)-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid 
• 258845-43-1 2-(3,5-dimethyl-isoxazole-4-sulfonylamino)-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid 
• 258845-41-9 2-benzenesulfonylamino-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid 

Relevant articles and documents

Isoxazolines as potent antagonists of the integrin α(v)β3

Starting with lead compound 2, we sought to increase the selectivity for α(v)β3-mediated cell adhesion by examining the effects of structural changes in both the guanidine mimetic and the substituent α to the carboxylate. To prepare some of the desired aminoimidazoles, a novel reductive amination utilizing a trityl-protected aminoimidazole was developed. It was found that guanidine mimetics with a wide range of pK(a)'s were potent antagonists of α(v)β3. In general, it appeared that an acylated 2-aminoimidazole guanidine mimetic imparted excellent selectivity for α(v)β3-mediated adhesion versus α(IIb)β3-mediated platelet aggregation, with selectivity of approximately 3 orders of magnitude observed for compounds 3g and 3h. It was also found in this series that the α- substituent was required for potent activity and that 2,6-disubstituted arylsulfonamides were optimal. In addition, the selective α(v)β3 antagonist 3h was found to be a potent inhibitor of α(v)β3-mediated cell migration.