71119-11-4

Basic information

• Product Name: 2-[2-HYDROXY-3-[2-(INDOL-3-YL)-1,1-DIMETHYLETHYLAMINO]PROPOXY]BENZONITRILE
• Synonyms: 2-[2-HYDROXY-3-[2-(INDOL-3-YL)-1,1-DIMETHYLETHYLAMINO]PROPOXY]BENZONITRILE;2-(2-hydroxy-3-((2-(1h-indol-3-yl)-1,1-dimethylethyl)amino)propoxy)benzonitr;Bucindolol;2-[2-Hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy]benzonitrile;3-[2-[3-(o-Cyanophenoxy)-2-hydroxypropylamino]-2-methylpropyl]-1H-indole;Benzonitrile, 2-(2-hydroxy-3-((2-(1H-indol-3-yl)-1,1-dimethylethyl)amino)propoxy)-;Bucindololum;Bucindololum [inn-latin]
• CAS NO: 71119-11-4
• Molecular Formula: C₂₂H₂₅N₃O₂
• Molecular Weight: 363.45
• Mol File: 71119-11-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 125-127°
• Boiling Point: 605.3°C at 760 mmHg
• Flash Point: 319.9°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 1.67E-15mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Store at +4°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.76±0.20(Predicted)
• CAS DataBase Reference: 2-[2-HYDROXY-3-[2-(INDOL-3-YL)-1,1-DIMETHYLETHYLAMINO]PROPOXY]BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-HYDROXY-3-[2-(INDOL-3-YL)-1,1-DIMETHYLETHYLAMINO]PROPOXY]BENZONITRILE(71119-11-4)
• EPA Substance Registry System: 2-[2-HYDROXY-3-[2-(INDOL-3-YL)-1,1-DIMETHYLETHYLAMINO]PROPOXY]BENZONITRILE(71119-11-4)

Safety Data

• Hazardous Substances Data: 71119-11-4(Hazardous Substances Data)

Usage

Uses

Antihypertensive.

Biological Activity

Non-selective β -adrenoceptor antagonist with additional α 1 -adrenoceptor blocking activity. K i values are 1.61, 1.20 and 68.9 nM for β 1 -, β 2 - and α 1 -adrenoceptors respectively. Also acts as a weak 5-HT 2A/2B antagonist. Displays vasodilatory and antihypertensive actions.

InChI:InChI=1/C22H25N3O2/c1-22(2,11-17-13-24-20-9-5-4-8-19(17)20)25-14-18(26)15-27-21-10-6-3-7-16(21)12-23/h3-10,13,18,24-26H,11,14-15H2,1-2H3

Upstream product

• 835-40-5 3-(2,2-dimethyl-2-nitroethyl)-1H-indole 
• 42864-99-3 (RS)-1-chloro-3-(2-cyanophenoxy)propan-2-ol 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 611-20-1 salicylonitrile 

Downstream Products

• 91476-03-8 (S),(R)-N-[3-(2-cyanophenoxy)-2-hydroxypropyl]-N-[1,1-dimethyl-2-(1H-indol-3-yl)ethyl]-N'-[1-(1-naphthyl)ethyl]urea 
• 91476-04-9 (R),(R)-N-[3-(2-cyanophenoxy)-2-hydroxypropyl]-N-[1,1-dimethyl-2-(1H-indol-3-yl)ethyl]-N'-[1-(1-naphthyl)ethyl]urea 

Relevant articles and documents

METHODS AND COMPOSITIONS INVOLVING (S)-BUCINDOLOL

Disclosed is bucindolol substantially free of its R-stereoisomer. Also disclosed are pharmaceutical compositions that include bucindolol substantially free of its R-stereoisomer or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. Also disclosed are methods of treating a patient that involve administering to the patient a therapeutically effective amount of a composition of the present invention. Formula (I).

ANTIHYPERTENSIVE THERAPY

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

3-INDOLYL-TERTIARY BUTYLAMINOPROPANOLS

1-Phenoxy-3-(3-indolyl)-tert.-butyl!amino-2-propanols and related 1-aryloxy compounds are antihypertensive agents having vasodilator and adrenergic β-receptor blocking action. Preferred compounds bear an ortho-substituent in the phenoxy group, and most preferably the cyano group.