103145-35-3

Basic information

• Product Name: (R)-2-(3,5-bis(benzyloxy)phenyl)oxirane
• Synonyms: (R)-2-(3,5-bis(benzyloxy)phenyl)oxirane
• CAS NO: 103145-35-3
• Molecular Weight: 332.399
• Mol File: 103145-35-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-2-(3,5-bis(benzyloxy)phenyl)oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(3,5-bis(benzyloxy)phenyl)oxirane(103145-35-3)
• EPA Substance Registry System: (R)-2-(3,5-bis(benzyloxy)phenyl)oxirane(103145-35-3)

Safety Data

• Hazardous Substances Data: 103145-35-3(Hazardous Substances Data)

Upstream product

• 103145-34-2 (R)-3’,5’-dibenzyloxyphenylbromohydrin 

Downstream Products

• 1026590-20-4 C₃₇H₃₇NO₃ 
• 1026184-18-8 C₄₅H₄₅NO₄ 
• 1026647-78-8 C₄₅H₄₅NO₄ 
• 1026431-67-3 C₃₉H₄₁NO₄ 
• 1026025-95-5 C₃₈H₃₈N₂O₅ 
• 1026408-27-4 C₃₈H₃₈N₂O₅ 
• 1026631-37-7 C₃₈H₃₉NO₃ 
• 1026407-81-7 C₃₆H₄₃NO₃ 
• 130156-24-0 (R,R)-(-)-Fenoterol 

Relevant articles and documents

Use of fenoterol and fenoterol analogues in the treatment of glioblastomas and astrocytomas

This disclosure concerns the discovery of the use of fenoterol and (R,R)- and (R,S)-fenoterol analogs for the treatment of a tumor expressing a β2-adrenergic receptor, such as a primary brain tumor, including a glioblastoma or astrocytoma expressing a β2-adrenergic receptor. In one example, the method includes administering to a subject a therapeutically effective amount of fenoterol, a specific fenoterol analog or a combination thereof to reduce one or more symptoms associated with the tumor, thereby treating the tumor in the subject.

Comparative molecular field analysis of fenoterol derivatives: A platform towards highly selective and effective β2-adrenergic receptor agonists

Purpose: To use a previously developed CoMFA model to design a series of new structures of high selectivity and efficacy towards the β2-adrenergic receptor. Results: Out of 21 computationally designed structures 6 compounds were synthesized and characterized for β2-AR binding affinities, subtype selectivities and functional activities. Conclusion: the best compound is (R,R)-4-methoxy-1-naphthylfelnoterol with Kiβ2-AR = 0.28 μm, Kiβ1-AR/Kiβ2-AR = 573, EC50cAMP = 3.9 nm, EC50cardio = 16 nm. The CoMFA model appears to be an effective predictor of the cardiomocyte contractility of the studied compounds which are targeted for use in congestive heart failure.

Comparative molecular field analysis of the binding of the stereoisomers of fenoterol and fenoterol derivatives to the β2 adrenergic receptor

Stereoisomers of fenoterol and six fenoterol derivatives have been synthesized and their binding affinities for the β2 adrenergic receptor (Kiβ2-AR), the subtype selectivity relative to the β1-AR (Kiβ1-AR/K iβ2-AR) and their functional activities were determined. Of the 26 compounds synthesized in the study, submicromolar binding affinities were observed for (R,R)-fenoterol, the (R,R)-isomer of the p-methoxy, and (R,R)- and (R,S)-isomers of 1-naphthyl derivatives and all of these compounds were active at submicromolar concentrations in cardiomyocyte contractility tests. The Kiβ1-AR/K iβ2-AR ratios were >40 for (R,R)-fenoterol and the (R,R)-p-methoxy and (R,S)-1-naphthyl derivatives and 14 for the (R,R)-1-napthyl derivative. The binding data was analyzed using comparative molecular field analysis (CoMFA), and the resulting model indicated that the fenoterol derivatives interacted with two separate binding sites and one steric restricted site on the pseudo-receptor and that the chirality of the second stereogenic center affected Kiβ2 and subtype selectivity.