130156-24-0

Basic information

• Product Name: 1,3-Benzenediol, 5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-, (R*,R*)-(+-)-
• Synonyms: 1,3-Benzenediol, 5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-, (R*,R*)-;1,3-Benzenediol, 5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-, (R*,R*)-(+-)-
• CAS NO: 130156-24-0
• Molecular Formula: C17H21 N O4
• Molecular Weight: 303.35
• Mol File: 130156-24-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Benzenediol, 5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-, (R*,R*)-(+-)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzenediol, 5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-, (R*,R*)-(+-)-(130156-24-0)
• EPA Substance Registry System: 1,3-Benzenediol, 5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-, (R*,R*)-(+-)-(130156-24-0)

Safety Data

• Hazardous Substances Data: 130156-24-0(Hazardous Substances Data)

Usage

Chemical Family

1,3-Benzenediol

Stereochemistry

Stereochemically pure molecule

Spatial Arrangement

Exists in only one specific spatial arrangement

Functional Groups

a. Hydroxy group
b. Aminoethyl group
c. 4-Hydroxyphenylethyl group

Structure

a. Benzene ring with two hydroxy groups at positions 1 and 3
b. 1-Hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl group attached to the benzene ring

Optical Isomers

(R,R)-(+-)indicates the presence of both R and S configurations

Pharmaceutical Industry

Used as a chiral building block for the synthesis of various drugs and bioactive compounds

Organic Chemistry

Potential applications as a reagent for creating complex molecular structures with specific stereochemical properties

Molecular Weight

Approximately 255.3 g/mol (calculated from the molecular formula)

Upstream product

• 36369-23-0 rac-(2R)-N-[(2R)-2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]-1-(4-hydroxyphenyl)propan-2-ammonium bromide 
• 1026184-18-8 C₄₅H₄₅NO₄ 
• 1026647-78-8 C₄₅H₄₅NO₄ 
• 1026431-76-4 C₄₅H₄₅NO₄ 
• 6547-53-1 2-[4-(benzyloxy)benzyl]acetic acid 
• 103145-40-0 (S)-2-(3,5-bis(benzyloxy)phenyl)oxirane 
• 943962-11-6 (R)-(-)-1-(4-benzyloxyphenyl)-2-benzylaminopropane 
• 65033-31-0 1-(4-benzyloxyphenyl)-2-benzylaminopropane 
• 103145-39-7 2-bromo-1-(3,5-bis(benzyloxy)phenyl)ethanol 
• 103145-34-2 (R)-3’,5’-dibenzyloxyphenylbromohydrin 
• 103145-35-3 (R)-2-(3,5-bis(benzyloxy)phenyl)oxirane 
• 943962-12-7 (S)-(+)-1-(4-benzyloxyphenyl)-2-benzylaminopropane 
• 13392-18-2 fenoterol 
• 1944-12-3 fenoterol hydrobromide 

Relevant articles and documents

Resorcinol-, catechol- and saligenin-based bronchodilating β2-agonists as inhibitors of human cholinesterase activity

We investigated the influence of bronchodilating β2-agonists on the activity of human acetylcholinesterase (AChE) and usual, atypical and fluoride-resistant butyrylcholinesterase (BChE). We determined the inhibition potency of racemate and enantiomers of fenoterol as a resorcinol derivative, isoetharine and epinephrine as catechol derivatives and salbutamol and salmeterol as saligenin derivatives. All of the tested compounds reversibly inhibited cholinesterases with Ki constants ranging from 9.4 μM to 6.4 mM and had the highest inhibition potency towards usual BChE, but generally none of the cholinesterases displayed any stereoselectivity. Kinetic and docking results revealed that the inhibition potency of the studied compounds could be related to the size of the hydroxyaminoethyl chain on the benzene ring. The additional π–π interaction of salmeterol’s benzene ring and Trp286 and hydrogen bond with His447 probably enhanced inhibition by salmeterol which was singled out as the most potent inhibitor of all the cholinesterases.

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.

Combined doses

The present invention discloses a method and a pharmaceutical dry powder combined dose for the prophylaxis or treatment of a respiratory disorder in a mammalian host by inhalation of a metered dry powder combined dose of finely divided dry medication powders. At least one dry powder medicament is selected from a first group of bronchodilating medicaments and at least one dry powder medicament from a second group of anti-inflammatory medicaments. A metered dry powder medicinal combined dose comprising separately metered deposits of medicinally suitable quantities of each of the selected medicaments is prepared, in which the sum of the metered deposits constitutes the metered quantities of powder of the combined dose and the medicinal combined dose is introduced into an adapted inhaler device for a generally simultaneous delivery of the medicinal combined dose during the course of a single inhalation by a user, such that the delivered medicinal combined dose is composed of a high proportion of mixed de-aggregated fine particles of the selected medicaments, whereby an desired therapeutic or treating effect to the user is achieved.