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

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

Uses

Used in Pharmaceutical Research:
1-EBIO is used as a research tool for studying the role of Ca2+-sensitive K+ channels in various physiological functions. Its activation of these channels helps researchers understand their involvement in different processes and potential therapeutic applications.
Used in Cystic Fibrosis Treatment:
1-EBIO is used as a potentiator for the residual function of mutant CFTR in rectal biopsies from cystic fibrosis patients. By enhancing the function of the mutant CFTR, it may help improve the symptoms and quality of life for individuals with this genetic disorder.
Used in Neuroscience Research:
1-EBIO is used as a modulator of electrical activity in rat central neurons, specifically in studying the effects of Ca2+-activated K+ channels on neuronal function. This application aids in understanding the role of these channels in neuronal communication and potential neurological disorders.
Used in Ion Channel Research:
1-EBIO is used as an activator of human intermediate conductance Ca2+-activated K+ channels, which helps researchers investigate the properties and functions of these channels in human physiology. This knowledge can be applied to develop targeted therapies for various conditions related to ion channel dysfunction.

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

• 23838-73-5 N-ethyl-benzene-1,2-diamine 
• 20885-66-9 o-(Ethylamino)benzohydroxamsaeure 
• 39573-31-4 1-ethyl-1H-benzo[d]imidazole-2(3H)-thione 
• 10112-15-9 N-Ethyl-2-nitroaniline 
• 1048344-54-2 1-(2-bromophenyl)-1-(ethyl)urea 
• 103-69-5 N-ethyl-N-phenylamine 
• 33758-39-3 N-ethyl-N-phenyl carbamoyl chloride 
• 530-62-1 1,1'-carbonyldiimidazole 
• 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 

Downstream Products

• 929564-97-6 1-[(1R)-3-chloro-1-phenylpropyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one 
• 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 
• 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.

Hypervalent iodine oxidative rearrangement of anthranilamides, salicylamides and some β-substituted amides: A new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds

Oxidation of anthranilamides, salicylamides and some β-substituted amides with iodobenzene diacetate in methanolic potassium hydroxide led to a new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds, respectively. The reaction probably occurs via initial Hofmann-type rearrangement followed by intramolecular cyclization of intermediate isocyanate.

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.

Highly efficient synthesis of ureas and carbamates from amides by iodosylbenzene-induced hofmann rearrangement

A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. Symmetric and asymmetric ureas and carbamates can be prepared by this procedure in up to 98 % yield. Ureidopeptides can also be prepared in good yield by this method. A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. By using this method, heterocyclic products can be easily obtained in excellent yield. Ureidopeptides can also be prepared in good yield by this procedure. Copyright

CYCLOHEXYL AMIDE DERIVATIVES AS CRF RECEPTOR ANTAGONISTS

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

1- Or 3-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2- ones: Potent, selective, and orally efficacious norepinephrine reuptake inhibitors

Sequential structural modifications of the aryloxypropanamine template (e.g., atomoxetine, 2) led to a novel series of 1-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors (NRIs). In general, this series of compounds potently blocked the human norepinephrine transporter (hNET) while exhibiting selectivity at hNET against both the human serotonin (hSERT) and dopamine transporters (hDAT). Numerous compounds (e.g., 19-22) had low nonamolar hNET potency with IC 50 values of 7-10 nM and excellent selectivity (>500 fold) at hNET over hSERT and hDAT. Several compounds, such as 20 and 22, were tested in a telemetric rat model of ovariectomized-induced thermoregulatory dysfunction and were efficacious at oral doses of 3 mg/kg in reducing the tail skin temperature. In addition, compound 20 was also studied in the rat hot plate and spinal nerve ligation (SNL) models of acute and neuropathic pain, respectively, and was orally efficacious at doses of 3-10 mg/kg.

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.

Synthesis and activity of novel 1- or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors

A series of novel 1- or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors was discovered. Several compounds such as 15 and 20 showed good hNET potency. Compounds 15 and 20 also displayed excellent selectivity at hNET that appeared superior to those of reboxetine and atomoxetine (4 and 5).

Substituted propylamine derivatives and methods of their use

The present invention is directed to substituted propylamine derivatives of formula I: or a pharmaceutically acceptable salt thereof, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromylagia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.

Copper-promoted/catalyzed C-N and C-O bond cross-coupling with vinylboronic acid and its utilities

The mildest method of N-vinylation has been discovered. The synthetic utilities of the N- and O-vinylated products include protecting group, cyclopropanation and Grubbs' ring closure metathesis reactions.