112281-28-4

Basic information

• Product Name: 5-(2-Oxiranyl)-8-(phenylMethoxy)-2(1H)-quinolinone
• Synonyms: 5-(2-Oxiranyl)-8-(phenylMethoxy)-2(1H)-quinolinone
• CAS NO: 112281-28-4
• Molecular Formula: C₁₈H₁₅NO₃
• Molecular Weight: 293
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 112281-28-4.mol

Chemical Properties

• Melting Point: 114-116 °C
• Boiling Point: 556.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.298±0.06 g/cm3(Predicted)
• Solubility: Chloroform
• PKA: 10.92±0.70(Predicted)
• CAS DataBase Reference: 5-(2-Oxiranyl)-8-(phenylMethoxy)-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-Oxiranyl)-8-(phenylMethoxy)-2(1H)-quinolinone(112281-28-4)
• EPA Substance Registry System: 5-(2-Oxiranyl)-8-(phenylMethoxy)-2(1H)-quinolinone(112281-28-4)

Safety Data

• Hazardous Substances Data: 112281-28-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(2-Oxiranyl)-8-(phenylMethoxy)-2(1H)-quinolinone is used as a key intermediate in the synthesis of various pharmaceutical compounds, including quinolones, benzoxazolones, and benzoxazinones. These synthesized compounds serve as β agonists, which are crucial in the treatment of respiratory diseases by helping to relax the smooth muscles in the airways and improve breathing.
Used in Respiratory Disease Treatment:
In the field of respiratory medicine, 5-(2-Oxiranyl)-8-(phenylMethoxy)-2(1H)-quinolinone is utilized as a precursor for the development of β agonist drugs. These drugs are specifically designed to target and activate β-adrenergic receptors in the respiratory system, leading to the relaxation of bronchial muscles and alleviation of symptoms associated with respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD). The use of 5-(2-Oxiranyl)-8-(phenylMethoxy)-2(1H)-quinolinone in the development of β agonists contributes to the improvement of patients' quality of life and the management of their respiratory health.

Upstream product

• 93609-84-8 5-acetyl-8-benzyloxy-1H-quinolin-2-one 
• 62978-73-8 5-acetyl-8-hydroxy-2(1H)-quinolinone 
• 148-24-3 8-quinolinol 
• 956234-40-5 8-(benzyloxy)-5-(2-bromo-1-hydroxyethyl)quinolin-2(1H)-one 
• 100331-89-3 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one 
• 869868-63-3 8-benzyloxy-5-(2-chloro-1-hydroxy-ethyl)-1H-quinolin-2-one 
• 108835-26-3 8-(benzyloxy)-5-(hydroxymethyl)quinoline N-oxide 
• 108835-27-4 8-(benzyloxy)quinoline-5-carboxaldehyde N-oxide 
• 108835-25-2 8-(benzyloxy)-5-(hydroxymethyl)quinoline 
• 100-39-0 benzyl bromide 
• 4053-44-5 5-(hydroxymethyl)-8-hydroxyquinoline 
• 147002-43-5 2-(8-hydroxy-2-oxo-1H-quinolin-5-yl)-2-hydroxyacetic acid 
• 15450-76-7 8-Hydroxy-1H-quinolin-2-one 
• 15450-72-3 2-oxo-1,2-dihydroquinolin-8-yl acetate 

Downstream Products

• 226991-46-4 5-[2-(N-phenethyl)-1-hydroxyethylamino]-8-(benzyloxy)-2(1H)-quinolinone 
• 1027282-06-9 C₂₇H₃₅N₃O₅ 

Relevant articles and documents

Synthesis and biological evaluation of β2-adrenoceptor agonists bearing the 2-amino-2-phenylethanol scaffold

A new series of β2-adrenoceptor agonists bearing the 2-amino-2-phenylethanol scaffold was synthesized. Evaluation of the compounds using cell assays and an in vitro guinea pig trachea relaxation assay showed that 8-hydroxy-5-(2-hydroxy-1-((4-hy

Discovery of β-arrestin-biased β2-adrenoceptor agonists from 2-amino-2-phenylethanol derivatives

β-Arrestins are a small family of proteins important for signal transduction at G protein-coupled receptors (GPCRs). β-Arrestins are involved in the desensitization of GPCRs. Recently, biased ligands possessing different efficacies in activating the G protein- versus the β-arrestin-dependent signals downstream of a single GPCR have emerged, which can be used to selectively modulate GPCR signal transduction in such a way that desirable signals are enhanced to produce therapeutic effects while undesirable signals of the same GPCR are suppressed to avoid side effects. In the present study, we evaluated agonist bias for compounds developed along a drug discovery project of β2-adrenoceptor agonists. About 150 compounds, including derivatives of fenoterol, 2-amino-1-phenylethanol and 2-amino-2-phenylethanol, were obtained or synthesized, and initially screened for their β-adrenoceptor-mediated activities in the guinea pig tracheal smooth muscle relaxation assay or the cardiomyocyte contractility assay. Nineteen bioactive compounds were further assessed using both the HTRF cAMP assay and the PathHunter β-arrestin assay. Their concentration-response data in stimulating cAMP synthesis and β-arrestin recruitment were applied to the Black–Leff operational model for ligand bias quantitation. As a result, three compounds (L-2, L-4, and L-12) with the core structure of 5-(1-amino-2-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one were identified as a new series of β-arrestin-biased β2-adrenoceptor agonists, whereas salmeterol was found to be Gs-biased. These findings would facilitate the development of novel drugs for the treatment of both heart failure and asthma.

Beta2-receptorexcitant and preparation method and application thereof

The invention relates to a following formula I showed compound in a free form, a salt form or a solvated form and having a beta2-receptor exciting effect. II and III are contained in R1, Ar are following formula groups IV and V, definition of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R13, R14, R15, R16, m and o is shown in the description. The invention further relates to a preparation method of the compound and application of a compound serving as a drug, in particular to treatment of diseases such as a chronic obstructive pulmonary disease, asthma and heart failure the aspects of a respiratory and cardiovascular system and a cardiovascular system.

HYDROXY-SUBSTITUTED BENZO-CONDENSED HETEROCYCLES FOR USE AS BETA AGONISTS IN THE TREATMENT OF RESPIRATORY DISEASES

The invention relates to the compounds of general formula (1), wherein the groups n, A, B, R1, R2 and R3 are defined as in the claims and in the description, and to methods for producing the same. The invention also relates to the use of these compounds as drugs, especially as drugs for use in the treatment of respiratory diseases.

Beta agonists for the treatment of respiratory diseases

The present invention relates to compounds of general formula 1 wherein the groups n, A, B, R1, R2 and R3 may have the meanings given in the claims and in the specification, processes for preparing them, and their use as pharmaceutical compositions, particularly as pharmaceutical compositions for the treatment of respiratory complaints.

Structure-affinity profile of 8-hydroxycarbostyril-based agonists that dissociate slowly from the β2-adrenoceptor

Several carbostyril-based β-agonists have been shown to bind tightly to and slowly dissociate from the β2-adrenoceptor (β2AR). In the present study, the structural features of 8-hydroxy-5-[2-[(1-phenyl-2-methylprop-2- yl)amino]-1-hydroxyethyl]-carbostyril (11a) which contribute to its binding properties at the β2AR were investigated using a series of synthesized analogs. The k(off), estimated by the rate of cAMP decline in DDT1 MF-2 (DDT) cells with a reduced receptor density, K(i) and ligand-induced receptor reductions were determined. All of the derivatives stimulated cAMP accumulation in DDT cells in the sub to mid nanomolar range and elicited the same maximal stimulation as (-)isoproterenol. Derivatives of 11a with side chain N-substitutions comprising 2-methylbutyl, phenylethyl and isopropyl had higher k(off)-values and lower affinities as compared to 11a. Increasing the number of methylenes between the side chain tertiary alpha carbon and phenyl from 1 in 11a to 3 or reducing the number to 0 also resulted in derivatives with higher k(off)- and K(i)-values). In addition, replacement of the 8- hydroxycarbostyril nucleus of 11a with catechol reduced the affinity of the compound for the β2AR by 48-fold and increased its k(off). Only those derivatives with the lowest k(off)-values induced a decrease in the receptor density of DDT cell membranes following a preincubation and extensive washing. The data show that the 8-hydroxycarbostyril nucleus in conjunction with substitutions on the tertiary alpha carbon of the side chain and positioning of the phenyl group are important characteristics determining the high affinity and slow dissociation of 11a from the β2AR.

Carbostyril Derivatives Having Potent β-Adrenergic Agonist Properties

Derivatives carrying a substituent in the para position of the phenyl group of 8-hydroxy-5--1-hydroxyethyl>carbostyril (10) were prepared and their effects on β-adrenoceptors evaluated in vitro.Unsubstituted compound