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4-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL - CAS 212485-91-1

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Category
Main Product
Product Name
4-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL
Catalog Number
212485-91-1
Synonyms
4-imidazolidin-2-ylidenecyclohexa-2,5-dien-1-one;4-(4,5-Dihydro-1H-imidazol-2-yl)phenol;212485-91-1;666092_ALDRICH;SCHEMBL1882160;4-(1-Imidazoline-2-yl)phenol
CAS Number
212485-91-1
Molecular Weight
0
Molecular Formula
C9H10N2O
COA
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MSDS
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Canonical SMILES
C1CNC(=C2C=CC(=O)C=C2)N1
InChI
InChI=1S/C9H10N2O/c12-8-3-1-7(2-4-8)9-10-5-6-11-9/h1-4,10-11H,5-6H2
InChIKey
LULFCHDWJWJYTP-UHFFFAOYSA-N
Structure
CAS 212485-91-1 4-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL
Specification
Purity
95%
Boiling Point
309.617ºC at 760 mmHg
Melting Point
280ºC ( dec.)
Density
1.217g/cm3
Appearance
white to tan powder, crystals or crystalline powder and/or chunks
Reference Reading
1.Pharmacological evidence that spinal α(2C)- and, to a lesser extent, α(2A)-adrenoceptors inhibit capsaicin-induced vasodilatation in the canine external carotid circulation.
Villalón CM1, Galicia-Carreón J, González-Hernández A, Marichal-Cancino BA, Manrique-Maldonado G, Centurión D. Eur J Pharmacol. 2012 May 15;683(1-3):204-10. doi: 10.1016/j.ejphar.2012.03.002. Epub 2012 Mar 14.
During a migraine attack capsaicin-sensitive trigeminal sensory nerves release calcitonin gene-related peptide (CGRP), producing cranial vasodilatation and central nociception; hence, trigeminal inhibition may prevent this vasodilatation and abort migraine headache. This study investigated the role of spinal α₂-adrenoceptors and their subtypes (i.e. α(2A), α(2B) and/or α(2C)-adrenoceptors) in the inhibition of the canine external carotid vasodilator responses to capsaicin. Anaesthetized vagosympathectomized dogs were prepared to measure arterial blood pressure, heart rate and external carotid conductance. The thyroid artery was cannulated for one-min intracarotid infusions of capsaicin, α-CGRP and acetylcholine. A cannula was inserted intrathecally for spinal (C₁-C₃) administration of 2-amino-6-ethyl-4,5,7,8-tetrahydro-6H-oxazolo-[5,4-d]-azepin-dihydrochloride (B-HT 933; a selective α₂-adrenoceptor agonist) and/or the α₂-adrenoceptor antagonists rauwolscine (α(2A/2B/2C)), 2-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-2,3-dihydro-1-methyl-1H-isoindole maleate (BRL44408; α(2A)), imiloxan (α(2B)) or acridin-9-yl-[4-(4-methylpiperazin-1-yl)-phenyl]amine (JP-1302; α(2C)).
2.Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine.
Nyrönen T1, Pihlavisto M, Peltonen JM, Hoffrén AM, Varis M, Salminen T, Wurster S, Marjamäki A, Kanerva L, Katainen E, Laaksonen L, Savola JM, Scheinin M, Johnson MS. Mol Pharmacol. 2001 May;59(5):1343-54.
We present a mechanism for agonist-promoted alpha(2A)-adrenergic receptor (alpha(2A)-AR) activation based on structural, pharmacological, and theoretical evidence of the interactions between phenethylamine ligands and alpha(2A)-AR. In this study, we have: 1) isolated enantiomerically pure phenethylamines that differ both in their chirality about the beta-carbon, and in the presence/absence of one or more hydroxyl groups: the beta-OH and the catecholic meta- and para-OH groups; 2) used [(3)H]UK-14,304 [5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-6-quinoxalinamine; agonist] and [(3)H]RX821002 [2-(2-methoxy-1,4-benzodioxan-2-yl)-2-imidazoline; antagonist] competition binding assays to determine binding affinities of these ligands to the high- and low-affinity forms of alpha(2A)-AR; 3) tested the ability of the ligands to promote receptor activation by measuring agonist-induced stimulation of [(35)S]GTPgammaS binding in isolated cell membranes; and 4) used automated docking methods and our alpha(2A)-AR model to predict the binding modes of the ligands inside the alpha(2A)-AR binding site.
3.A new ditopic ratiometric receptor for detecting zinc and fluoride ions in living cells.
Li YP1, Zhao Q, Yang HR, Liu SJ, Liu XM, Zhang YH, Hu TL, Chen JT, Chang Z, Bu XH. Analyst. 2013 Sep 21;138(18):5486-94. doi: 10.1039/c3an00351e. Epub 2013 Jul 29.
The synthesis, characterization and ion binding properties of a new ditopic ratiometric receptor (1), based on 2-(4,5-dihydro-1H-imidazol-2-yl)phenol and crown ether moieties, have been described. The ditopic ratiometric receptor has been studied in sensing both F(-) and Zn(2+) ions, exhibiting different fluorescent colour changes from cyan green to blue/black observable by the naked eye under UV-light. The addition of Zn(2+) to the solution of 1 induced the formation of a 2 : 2 ligand-metal complex 1-Zn(2+), which displays a remarkable blue shift of the emission maxima of 1 from 455 nm to 400 nm due to the inhibition of excited-state intramolecular proton transfer (ESIPT) mechanism. The sensing processes were monitored by fluorescence/absorption titrations, and further confirmed by Job's plot and (1)H NMR titrations. The crystal structure of 1-Zn(2+) reveals that 1 binds Zn(2+) in four-coordinated modes. Furthermore, 1 is cell permeable and may be applied to detect trace Zn(2+) and F(-) during the development of a living organism.
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