103145-34-2

Upstream product

• 28924-21-2 3,5-dibenzyloxyacetophenone 
• 28924-18-7 2-bromo-1-[3,5-bis(phenylmethoxy)phenyl]ethanone 

Downstream Products

• 103145-35-3 (R)-2-(3,5-bis(benzyloxy)phenyl)oxirane 
• 37394-31-3 (-)-Terbutaline 
• 53144-56-2 (R)‐5‐(2‐(tert‐butylamino)‐1‐hydroxyethyl)benzene‐1,3‐diol hydrochloride 
• 865799-46-8 [(R)-1-(3,5-bis-benzyloxy-phenyl)-2-bromo-ethoxy]-tert-butyl-dimethyl-silane 
• 130156-24-0 (R,R)-(-)-Fenoterol 
• 391234-97-2 (R,S)-5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol 
• 1026407-81-7 C₃₆H₄₃NO₃ 
• 1026631-37-7 C₃₈H₃₉NO₃ 

Relevant academic research and scientific papers

A method of preparing R-terbutaline

A method of preparing R-terbutaline is disclosed for the first time. According to the method, 3,5-dibenzyloxyacetophenone is adopted as an initial material, is subjected to a bromination reaction, and then reduced by borane-methyl sulfide complex under catalysis by S-methyl-CBS; a product is coupled with N-benzyl-tert-butylamine, and then is hydrogenated to remove benzyl to prepare optically pure R-terbutaline; and the R-terbutaline is salted by utilizing a corresponding acid to prepare a medical salt of the R-terbutaline.

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.

Surfactant-accelerated asymmetric transfer hydrogenation with recyclable water-soluble catalyst in aqueous media

Water-soluble ligands (R,R)-2 were successfully prepared, in which the bis-meta-sulphonated ligand was definitely detected as the major product. The corresponding transition-metal complexes containing the ligands displayed excellent catalytic performance in asymmetric transfer hydrogenation (ATH) of aromatic ketones. Especially, the aromatic ketones with a bromine group in the α position could be smoothly reduced to the expected alcohol, keeping the bromine group intact with excellent enantioselectivities (up to 96% ee). The catalyst could be reused at least 21 times without erosion of the enantioselectivity in high conversion. Moreover, it was found that cationic surfactant and proper pH values were necessary for the maintenance of high reactivity.

PREPARATION OF (R,R)-FENOTEROL AND (R,R)- OR (R,S)-FENOTEROL ANALOGUES AND THEIR USE IN TREATING CONGESTIVE HEART FAILURE

This disclosure concerns the discovery of (R,R)- and (R,S)-fenoterol analogues which are highly effective at binding β2-adrenergic receptors. Exemplary chemical structures for these analogues are provided. Also provided are pharmaceutical compositions including the disclosed (R,R)-fenoterol and fenoterol analogues, and methods of using such compounds and compositions for the treatment of cardiac disorders such as congestive heart failure and pulmonary disorders such as asthma or chronic obstructive pulmonary disease.

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.

Compounds for the treatment of diseases

The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.