10045-45-1

Basic information

• Product Name: 1-EBIO
• Synonyms: 1-Ethyl-1H-benzimidazole-2(3H)-one;1-Ethyl-2,3-dihydro-1H-benzimidazole-2-one;EBIO;1-Ethyl-2-benzimidazolinone,98%;Einecs 233-148-1;1-EB10;1-ethyl-1,3-dihydro-2H-benzimidazol-2-one(SALTDATA: FREE);1-EBIO, 1-Ethyl-2-benzimidazolinone
• CAS NO: 10045-45-1
• Molecular Formula: C₉H₁₀N₂O
• Molecular Weight: 162.19
• EINECS: 233-148-1
• Product Categories: Ion Channels;BENZIMIDAZOLE;Potassium channel
• Mol File: 10045-45-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 118-120 °C(Solv: ethyl acetate (141-78-6))
• Appearance: /
• Density: 1.161g/cm³
• Refractive Index: 1.566
• Storage Temp.: Store at RT
• Solubility: DMSO: ≥20mg/mL
• PKA: 12.29±0.30(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: 1-EBIO(CAS DataBase Reference)
• NIST Chemistry Reference: 1-EBIO(10045-45-1)
• EPA Substance Registry System: 1-EBIO(10045-45-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 10045-45-1(Hazardous Substances Data)

Usage

Description

1-EBIO is an activator of Ca2+-sensitive K+ channels (EC50 = 490 μM in T84 human carcinoma cells).This action is sensitive to the neurotoxin charybdotoxin (Ki = 3.5 nM). In mouse colonic epithelia, 1-EBIO also activates cAMP-sensitive K+ channels, a response this is inhibited by 293B.In this type of epithelium, but not mouse nasal epithelia, 1-EBIO activates both types of channels, resulting in large Cl- secretory currents.It also activates the human intermediate conductance Ca2+-activated K+ channel (EC50 = 74 μM).1-EBIO is currently used to study the role of these types of K+ channels in diverse physiological functions.

Uses

1-EBIO stimulates Cl- secretion in secretory epithelia through direct activation of clacium potassium channels.1-EBIO was used to study the electrical activity modulated by Ca+2-activated K+ channels in rat central neurons. The effect of 1-EBIO on human intermediate conductance channels was studied.The K+ channel opener 1-EBIO potentiates residual function of mutant CFTR in rectal biopsies from cystic fibrosis patients

Biological Activity

Activator of epithelial K Ca channels, stimulates a large and sustained trans-epithelial Cl - secretory response across T84 monolayers. Induces hyperpolarization to the same magnitude as ACh in aortic value endothelial cells.

References

1) Adeagbo?et al.?(1999),?1-Ethyl-2-benzimidazolinone stimulates endothelial K(Ca) channels and nitric oxide formation in rat mesenteric vessels; Eur. J. Pharmacol.,?379?151 2) Orfila?et al. (2014),?Increasing small conductance Ca2+-activated potassium channel activity reverses ischemia-induced impairment of long-term potentiation; Eur. J. Neurosci.,?40?3179 3) Allen?et al.?(2011),?SK2 channels are neuroprotective for ischemia-induced neuronal cell death; J. Cereb. Blood Flow Metab.,?31?2302 4) Muller?et al. (2012),?Ca2+ activated K channels-new tools to induce cardiac commitment from pluripotent stem cells in mice and men; Stem Cell Rev.,?8?720 5) Fay?et al.?(2006),?SK channels mediate NADPH oxidase-independent reactive oxygen species production and apoptosis in granulocytes; Proc. Natl. Acad. Sci. USA,?103?17548

InChI:InChI=1/C9H10N2O/c1-2-11-8-6-4-3-5-7(8)10-9(11)12/h3-6H,2H2,1H3,(H,10,12)

Upstream product

• 39573-31-4 1-ethyl-1H-benzo[d]imidazole-2(3H)-thione 
• 23838-73-5 N-ethyl-benzene-1,2-diamine 
• 530-62-1 1,1'-carbonyldiimidazole 
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• 33758-39-3 N-ethyl-N-phenyl carbamoyl chloride 
• 1048344-54-2 1-(2-bromophenyl)-1-(ethyl)urea 
• 10112-15-9 N-Ethyl-2-nitroaniline 
• 95-54-5 1,2-diamino-benzene 
• 60739-31-3 1-(1-phenylvinyl)-1H-benzo[d]imidazol-2(3H)-one 
• 31767-67-6 N-Ethylanthranilium fluoroborate 
• 599177-43-2 1-ethyl-3-hexen-1'-yl-2-benzimidazolinone 
• 74375-44-3 o-ethylaminobenzamide 
• 57-13-6 urea 
• 91202-08-3 N-Ethylanthraniloyl azide 

Downstream Products

• 1319742-74-9 trans-5-chloro-N-[4-(3-ethyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-cyclohexyl]-2-methyl-nicotinamide 
• 1057215-56-1 1-ethyl-3-[(1S,2S)-2,3-dihydroxy-1-phenyl-propyl]-1,3-dihydro-2H-benzimidazol-2-one 
• 929564-97-6 1-[(1R)-3-chloro-1-phenylpropyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one 
• 131728-72-8 N-(phenyl)-N-[1-(2-(3-ethyl-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)ethyl)-4-methoxycarbonyl-4-piperidinyl]propanamide 
• 131728-74-0 N-(phenyl)-N-[1-(2-(3-ethyl-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)ethyl)-4-methoxymethyl-4-piperidinyl]propanamide 
• 89659-88-1 1-Ethyl-3-pyridin-2-yl-1,3-dihydro-benzoimidazol-2-one 

Relevant articles and documents

Investigations of unsaturated azoles. 14. Reaction of benzimidazole and its derivatives with p-nitrostyrene oxide. Quaternary ammonium bases

The reactions of benzimidazole and its 2- and 1-alkyl, 2-mercapto, and 2-amino derivatives with p-nitrostyrene oxide have been studied. 1997 Plenum Publishing Corporation.

Photocatalytic Intramolecular C-H Amination Using N-Oxyureas as Nitrene Precursors

Nitrenes are remarkable high-energy chemical species that enable direct C-N bond formation, typically via controlled reactions of metal-stabilized nitrenes. Here, in contrast, the combined use of photocatalysis with careful engineering of the precursor enabled C-H amination forming imidazolidinones and related nitrogen heterocycles from readily accessible hydroxylamine precursors. Preliminary mechanistic results are consistent with the formation of free carbamoyl triplet nitrenes as reactive intermediates.

CYCLOHEXYL AMIDE DERIVATIVES AS CRF RECEPTOR ANTAGONISTS

There are described cydohexyl amide derivatives useful as corticotropin releasing factor (CRF) receptor antagonists

Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones

The copper-catalyzed intramolecular N-arylation of 2-bromoarylureas performed in water leading to the benzo[d]imidazolone framework is reported. The scope of the methodology presented herein proved to?be broad and afforded a significant number of benzoimidazolones in good to excellent yields. The reported protocol is based on the use of CuI and TMEDA acting both as the ligand and as the base in a water solution, which allows for the easy separation of the catalyst containing aqueous phase from the products by simple extraction. Additionally, the N- versus O-arylation competitive processes are also discussed.