177704-09-5

Basic information

• Product Name: (2S)-(+)-1-(3',4'-dibenzyloxyphenoxy)-2,3-epoxypropane
• Synonyms: (2S)-(+)-1-(3',4'-dibenzyloxyphenoxy)-2,3-epoxypropane
• CAS NO: 177704-09-5
• Molecular Weight: 362.425
• Mol File: 177704-09-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S)-(+)-1-(3',4'-dibenzyloxyphenoxy)-2,3-epoxypropane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-(+)-1-(3',4'-dibenzyloxyphenoxy)-2,3-epoxypropane(177704-09-5)
• EPA Substance Registry System: (2S)-(+)-1-(3',4'-dibenzyloxyphenoxy)-2,3-epoxypropane(177704-09-5)

Safety Data

• Hazardous Substances Data: 177704-09-5(Hazardous Substances Data)

Upstream product

• 27688-86-4 3,4-dibenzyloxyphenol 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 100-39-0 benzyl bromide 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 189082-97-1 3,4-bis(benzyloxy)phenyl formate 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 27688-87-5 (S)-3-(3,4-dibenzyloxyphenoxy)-1,2-epoxypropane 

Downstream Products

• 782436-39-9 (2S)-(-)-1-(3',4'-dibenzyloxyphenoxy)-3-(2-(3'',4''-dimethoxyphenyl)ethylamino)-2-propanol 
• 74513-77-2 (2S)-1-(3,4-dihydroxyphenoxy)-3-[2-(3',4'-dimethoxyphenyl)ethyl]amino-2-propanol 

Relevant articles and documents

Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

Starting from the β-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gαs, while they only show weak or even no β-arrestin-2 recruitment at both β1- and β2-AR. Molecular dynamics simulations suggest that the difference in G protein efficacy and β-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the β2-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser5.46 and Asn6.55, and the aromatic head group of the ligands.

Synthesis and β-adrenoceptor agonist properties of (±)-1-(3',4'- dihydroxyphenoxy)-3-(3',4'-dimethoxyphenyl) ethylamino-2-propanol hydrochloride, (±)-RO363.HCl, and the (2S)-(-)-isomer

The synthesis of (±)-1-(3',4'-dihydroxyphenoxy)-3-(3',4'- dimethoxyphenyl)ethylamino-2-propanol hydrochloride, (±)RO363.HCl, and the (2S)-(-)-isomer is described for the first time. The binding affinities for (±)-RO363.HCl, (2S)-(-)-RO363.HCl and a number of well known β-adrenoceptor agonists for transfected humanβ1,-, β2- and β3-adrenoceptors expressed in Chinese hamster ovary cells have been determined and compared with the functional potencies in rat atria (β1) and trachea (β2). The results indicate that both (±)-RO363 and (2S)-(-)-RO363 are selective for the human and rat β1-adrenoceptors. The (2S)-(-)-isomer of RO363, as expected, has a higher binding affinity for the human and functional potency for rat β- adrenoceptor subtypes than the racemate. However, in contrast to the catecholamines and formoterol, the functional potency of the racemic mixture and its (-)-enantiomer are not significantly different from their binding affinity, suggesting that they are examples of partial agonists with sufficient intrinsic activity to produce full agonist responses.