5586-92-5

Usage

InChI:InChI=1/C16H16O2/c1-13(17)11-14-7-9-16(10-8-14)18-12-15-5-3-2-4-6-15/h2-10H,11-12H2,1H3

Upstream product

• 93969-55-2 1-benzyloxy-4-(2-nitropropyl)benzene 
• 100780-36-7 (E)-1-(benzyloxy)-4-(2-nitroprop-1-enyl)benzene 
• 770-39-8 4-methoxyphenylacetone 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 6547-53-1 2-[4-(benzyloxy)benzyl]acetic acid 
• 108-24-7 acetic anhydride 
• 56441-69-1 2-<4-(phenylmethoxy)phenyl>acetic acid ethyl ester 
• 917-54-4 methyllithium 

Downstream Products

• 65033-31-0 1-(4-benzyloxyphenyl)-2-benzylaminopropane 
• 943962-11-6 (R)-(-)-1-(4-benzyloxyphenyl)-2-benzylaminopropane 
• 943962-12-7 (S)-(+)-1-(4-benzyloxyphenyl)-2-benzylaminopropane 
• 1026184-18-8 C₄₅H₄₅NO₄ 
• 1026647-78-8 C₄₅H₄₅NO₄ 
• 1026431-76-4 C₄₅H₄₅NO₄ 
• 391234-97-2 (R,S)-5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol 
• 130156-24-0 (S,R)-5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol 
• 130156-24-0 (S,S)-(+)-Fenoterol 
• 130156-24-0 (R,R)-(-)-Fenoterol 
• 78069-47-3 1-(4-benzyloxyphenyl) propan-2-one ethylene ketal 
• 770-39-8 4-methoxyphenylacetone 

Relevant academic research and scientific papers

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.

Rational design, synthesis and structure-activity relationships of 4-alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues as novel tyrosinase inhibitors

In continuing our program aimed to search for potent compounds as highly efficient tyrosinase inhibitors, here a series of novel 4-alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues were designed, synthesized and their biological activities on mushroom tyrosinase were evaluated. Notably, most of compounds displayed remarkable tyrosinase inhibitory activities with IC50 value of lower than 1.0 μM. Furthermore, the structure-activity relationships (SARs) were discussed and the inhibition mechanism and the inhibitory kinetics of selected compounds 7k and 8d were also investigated. Taken together, these results suggested that such compounds could serve as the promising candidates for the treatment of tyrosinase-related disorders and further development of such compounds might be of great interest.

Pyrazolo[1,5-a]pyrimidine-based inhibitors of HCV polymerase

The present paper describes a novel series of HCV RNA polymerase inhibitors based on a pyrazolo[1,5-a]pyrimidine scaffold bearing hydrophobic groups and an acidic functionality. Several compounds were optimized to low nanomolar potencies in a biochemical RdRp assay. SAR trends clearly reveal a stringent preference for a cyclohexyl group as one of the hydrophobes, and improved activities for carboxylic acid derivatives.

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.

Mass spectrometric investigations on phenylacetic acid derivatives, IV: Loss of ortho-substituents from ionized phenyl-2-propanones upon electron impact

In the gas phase, the phenyl-2-propanone molecules 2a-4a lose upon electron impact chloro-, bromo-, and iodo-radicals specifically at the orthopOsition of the phenyl group giving rise to strong (M-Hal.)+-ions (70/12 eV; 1st and 2nd FFR) of identical structure as confirmed by their MIKE-CAD-spectra. The daughter ions at m/z 133 from o-chlorophenyl-2-propanone (2a) and 2,2-dimethyl-2,3-dihydro[b]furane (11) are structurally similar but not identical (similarity index 99.8). The collisionally activated (2nd FFR) (M-Br.)+-ions from o-bromophenyl-2-propanone (3a) and 1-bromo-1-phenyl-2-propanone (12) produce virtually congruent spectra. The most impOrtant subsequent fragmentation of the (M-Hal-)+-ions from 2a-4a is the loss of CO which incorporates the C-atom of the carbonyl group exclusively (13C labelling). Mechanistic aspects of the fragmentation sequences are discussed (Figs. 5 and 8).

Reduction of Oximes and Aliphatic Nitro Compounds to Imines for Further in situ Reactions: A Novel Synthesis of Pyrroles and Pyrrolin-2-ones

Tributhylphosphine-diphenyl disulphide is a self-drying reagent capable of reducing ketoximes and secondary aliphatic nitro compounds to the corresponding imines under strictly anhydrous conditions at room temperature.The imine may be hydrolysed to a ketone, acetylated to give an enamide, reduced to an amine , or captured by hydrogen cyanide to produce an α-amino nitrile.In the case of 1,4-nitro ketones or esters, intramolecular cyclisation leads to pyrroles or pyrrolin-2-ones.Aldoximes and primary nitro compounds are converted into nitriles by the reagent.Hydroxamic acids are reduced to the corresponding amides.

A MILD REDUCTION OF ALIPHATIC NITRO COMPOUNDS TO IMINES FOR FURTHER IN SITU REACTIONS : A SIMPLE SYNTHESIS OF PYRROLES

Tributylphosphine-diphenyldisulphide reduces nitroalkanes to imines which can be trapped intramolecularly to give pyrroles.

Ethanamine derivatives their preparation and use in pharmaceutical compositions

The compounds of formula (II): STR1 in which R1 is a hydrogen, fluorine, chlorine or bromine atom or a hydroxyl, hydroxymethyl, methyl, methoxyl, amino, formamido, acetamido, methylsulphonylamido, nitro, benzyloxy, methylsulphonylmethyl, ureido, trifluoromethyl or p-methoxybenzylamino group; R2 is a hydrogen, fluorine, chlorine or bromine atom or a hydroxyl group; R3 is a hydrogen, chlorine or bromine atom or a hydroxyl group, R4 is a hydrogen atom or a methyl group; R5 is a hydrogen atom or a methyl group; R6 is a hydrogen, fluorine or chlorine atom or a methyl, methoxyl or hydroxy group; X is an oxygen atom or a bond; Y is an alkylene group of up to 6 carbon atoms or a bond; and Z is an alkylene, alkenylene or alkynylene group of up to 10 carbon atoms, have been found to possess anti-obesity and/or anti-hyperglycaemic activity.

Synthesis of bronchospasmolytically effective β phenylethyl aminoalkyl xanthines

New theophylline and theobromine derivatives are synthesized from the β phenylethylaminoalkyl xanthines, whose phenyl substituent is substituted by one or two hydroxyl groups and partially also by other substituents. Different methods of synthesis are described, among them the production of the bronchospasmolytic 7 (3 [2 (3,5 dihydroxyphenyl) 2 hydroxy ethylamino] propyl) theophylline (reproterol . HCl).