53671-71-9

Basic information

• Product Name: ICI 89406
• Synonyms: N-[2-[3-(2-CYANOPHENOXY)-2-HYDROXYPROPYLAMINO]ETHYL]-N'-PHENYLUREA;ICI 89406;C025716;Urea, N-(2-((3-(2-cyanophenoxy)-2-hydroxypropyl)amino)ethyl)-N'-phenyl-
• CAS NO: 53671-71-9
• Molecular Formula: C₁₉H₂₂N₄O₃
• Molecular Weight: 354.4
• Mol File: 53671-71-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 155-156 °C(Solv: acetonitrile (75-05-8))
• Boiling Point: 575 °C at 760 mmHg
• Flash Point: 301.5 °C
• Appearance: /
• Density: 1.25 g/cm³
• Storage Temp.: Store at RT
• PKA: 12.29±0.46(Predicted)
• CAS DataBase Reference: ICI 89406(CAS DataBase Reference)
• NIST Chemistry Reference: ICI 89406(53671-71-9)
• EPA Substance Registry System: ICI 89406(53671-71-9)

Safety Data

• Hazardous Substances Data: 53671-71-9(Hazardous Substances Data)

Usage

Uses

ICI 89406 is beta-1-selective antagonist.

Biological Activity

β -adrenergic antagonist and low efficacy partial agonist; does not affect resting cardiac parameters.

Upstream product

• 53673-01-1 1-(2-aminoethyl)-3-phenylurea 
• 38465-16-6 1,2-epoxy-3-(2-cyanophenyl)propane 
• 611-20-1 salicylonitrile 
• 215654-49-2 tert-butyl (2-(3-phenylureido)ethyl)carbamate 
• 85850-48-2 2-<<(phenylamino)carbonyl>amino>ethylamine hydrochloride 

Relevant articles and documents

Design of new beta1-selective adrenoceptor ligands as potential radioligands for in vivo imaging.

In general, the failing human heart is characterized by a selective reduction in beta(1)-adrenoceptors (beta(1)-ARs) without change in beta(2)-AR density. Medical imaging techniques, either single photon emission computed tomography (SPECT) or positron emission tomography (PET) with appropriate radioligands, offer the possibility of assessing beta-adrenoceptor density non-invasively in humans. To date, neither a SPECT nor a PET radioligand is available for the selective imaging of cardiac beta(1)-ARs. The aim of this study was to develop potential high affinity beta(1)-selective AR radioligands for the non-invasive in vivo imaging of the beta(1)-AR density in the human heart using SPECT or PET. A variety of racemic N-aryl-N'-[2-[3-aryloxy-2-hydroxy-propylamino]-ethyl]-urea derivatives and chain-elongated analogues, related to the established beta(1)-AR antagonist, ICI 89,406 8i, were synthesized. Competition studies using the non-selective AR ligand, [(125)I]iodocyanopindolol ([(125)I]ICYP), and ventricular membrane preparations of wild-type mice revealed nine ligands with higher beta(1)-AR affinities (up to 76-fold) and beta(1)-AR selectivities (up to 139-fold) than 8i. Mostly, these ligands possess a 2-substituted phenoxy group and a 4-substituted phenyl residue in contrast to the lead compound 8i. The non-radioactive counterparts of the desired SPECT- and PET-radiotracers were synthesized as reference compounds [e.g., 8f, 8g, 8h and 8l as the non-radioactive analogues of the radioiodinated SPECT radioligands, 8e and 8h as the non-radioactive compounds of C-11 labelled PET-tracers (C-11 in the methoxy group)]. The established library of high affinity beta(1)-selective AR antagonists was screened for chemical precursors for the radiosynthesis of the mentioned radioligands. Furthermore, the library consists of some comparison compounds that are unsubstituted, allyl- and alkyl-substituted or chain-elongated (e.g., 8a, 8j, 8o and 8r-t). Future steps will include radiolabelling and pharmacokinetic evaluation of the beta(1)-selective target compounds, which could be applied as sympathetic innervation agents for in vivo investigations and diagnostics in patients suffering from cardiac diseases like heart failure and ventricular arrhythmias.