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Home > Imidazoles > 10045-45-1
10045-45-1 | 2H-Benzimidazol-2-one, 1-ethyl-1,3-dihydro-
CAS No: 10045-45-1 Catalog No: AG000217 MDL No:MFCD00005715
Product Description
Catalog Number:
AG000217
Chemical Name:
2H-Benzimidazol-2-one, 1-ethyl-1,3-dihydro-
CAS Number:
10045-45-1
Molecular Formula:
C9H10N2O
Molecular Weight:
162.1885
MDL Number:
MFCD00005715
IUPAC Name:
3-ethyl-1H-benzimidazol-2-one
InChI:
InChI=1S/C9H10N2O/c1-2-11-8-6-4-3-5-7(8)10-9(11)12/h3-6H,2H2,1H3,(H,10,12)
InChI Key:
CXUCKELNYMZTRT-UHFFFAOYSA-N
SMILES:
CCn1c(=O)[nH]c2c1cccc2
EC Number:
233-148-1
UNII:
M82W79SS4W
Properties
Complexity:
193
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
162.079g/mol
Formal Charge:
0
Heavy Atom Count:
12
Hydrogen Bond Acceptor Count:
1
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
162.192g/mol
Monoisotopic Mass:
162.079g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
32.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.1
Literature
| Title | Journal |
|---|---|
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| Why mouse airway submucosal gland serous cells do not secrete fluid in response to cAMP stimulation. | The Journal of biological chemistry 20121102 |
| Cerebellar ataxia by enhanced Ca(V)2.1 currents is alleviated by Ca2+-dependent K+-channel activators in Cacna1a(S218L) mutant mice. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20121031 |
| Mechanisms of bicarbonate secretion: lessons from the airways. | Cold Spring Harbor perspectives in medicine 20120801 |
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| Expression and Role of the Intermediate-Conductance Calcium-Activated Potassium Channel KCa3.1 in Glioblastoma. | Journal of signal transduction 20120101 |
| K(Ca)2 and k(ca)3 channels in learning and memory processes, and neurodegeneration. | Frontiers in pharmacology 20120101 |
| Towards therapeutic applications of arthropod venom k(+)-channel blockers in CNS neurologic diseases involving memory acquisition and storage. | Journal of toxicology 20120101 |
| Identification of the functional binding pocket for compounds targeting small-conductance Ca²⁺-activated potassium channels. | Nature communications 20120101 |
| SK2 channels are neuroprotective for ischemia-induced neuronal cell death. | Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20111201 |
| Calcium-activated potassium channel KCa3.1 in lung dendritic cell migration. | American journal of respiratory cell and molecular biology 20111101 |
| Evidence for aconitine-induced inhibition of delayed rectifier K(+) current in Jurkat T-lymphocytes. | Toxicology 20111028 |
| Functional reduction of SK3-mediated currents precedes AMPA-receptor-mediated excitotoxicity in dopaminergic neurons. | Neuropharmacology 20110601 |
| Negative gating modulation by (R)-N-(benzimidazol-2-yl)-1,2,3,4-tetrahydro-1-naphthylamine (NS8593) depends on residues in the inner pore vestibule: pharmacological evidence of deep-pore gating of K(Ca)2 channels. | Molecular pharmacology 20110601 |
| Small conductance calcium-activated potassium type 2 channels regulate alcohol-associated plasticity of glutamatergic synapses. | Biological psychiatry 20110401 |
| Calmodulin-dependent activation of the epithelial calcium-dependent chloride channel TMEM16A. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20110301 |
| Endothelium-dependent vasodilation in human mesenteric artery is primarily mediated by myoendothelial gap junctions intermediate conductance calcium-activated K+ channel and nitric oxide. | The Journal of pharmacology and experimental therapeutics 20110301 |
| Use of intermediate/small conductance calcium-activated potassium-channel activator for endothelial protection. | The Journal of thoracic and cardiovascular surgery 20110201 |
| Diet-induced obesity impairs endothelium-derived hyperpolarization via altered potassium channel signaling mechanisms. | PloS one 20110101 |
| An SK3 channel/nWASP/Abi-1 complex is involved in early neurogenesis. | PloS one 20110101 |
| The K+ channel opener 1-EBIO potentiates residual function of mutant CFTR in rectal biopsies from cystic fibrosis patients. | PloS one 20110101 |
| Modulation of calcium-activated potassium channels induces cardiogenesis of pluripotent stem cells and enrichment of pacemaker-like cells. | Circulation 20101102 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Small conductance calcium-activated potassium channels: from structure to function. | Progress in neurobiology 20100701 |
| Reduced nucleus accumbens SK channel activity enhances alcohol seeking during abstinence. | Neuron 20100311 |
| In vivo pharmacological manipulation of small conductance Ca(2+)-activated K(+) channels influences motor behavior, object memory and fear conditioning. | Neuropharmacology 20100301 |
| Expression of Ca2+ -activated K+ channels in human dermal fibroblasts and their roles in apoptosis. | Skin pharmacology and physiology 20100101 |
| Ictal activity induced by group I metabotropic glutamate receptor activation and loss of afterhyperpolarizations. | Neuropharmacology 20100101 |
| K+ channel openers restore verapamil-inhibited lung fluid resolution and transepithelial ion transport. | Respiratory research 20100101 |
| Identification and functional characterization of the intermediate-conductance Ca(2+)-activated K(+) channel (IK-1) in biliary epithelium. | American journal of physiology. Gastrointestinal and liver physiology 20091101 |
| Selective activation of the SK1 subtype of human small-conductance Ca2+-activated K+ channels by 4-(2-methoxyphenylcarbamoyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (GW542573X) is dependent on serine 293 in the S5 segment. | Molecular pharmacology 20090901 |
| A positive modulator of K Ca 2 and K Ca 3 channels, 4,5-dichloro-1,3-diethyl-1,3-dihydro-benzoimidazol-2-one (NS4591), inhibits bladder afferent firing in vitro and bladder overactivity in vivo. | The Journal of pharmacology and experimental therapeutics 20090101 |
| Synthesis and structure-activity relationship studies of 2-(N-substituted)-aminobenzimidazoles as potent negative gating modulators ofsmall conductance Ca2+-activated K+ channels. | Journal of medicinal chemistry 20081211 |
| SK (KCa2) channels do not control somatic excitability in CA1 pyramidal neurons but can be activated by dendritic excitatory synapses and regulate their impact. | Journal of neurophysiology 20081101 |
| Molecular and cellular basis of small--and intermediate-conductance, calcium-activated potassium channel function in the brain. | Cellular and molecular life sciences : CMLS 20081001 |
| Engagement of the EP2 prostanoid receptor closes the K+ channel KCa3.1 in human lung mast cells and attenuates their migration. | European journal of immunology 20080901 |
| Temporal processing across multiple topographic maps in the electrosensory system. | Journal of neurophysiology 20080801 |
| IK1 channel activity contributes to cisplatin sensitivity of human epidermoid cancer cells. | American journal of physiology. Cell physiology 20080601 |
| Calcium-activated potassium currents differentially modulate respiratory rhythm generation. | The European journal of neuroscience 20080601 |
| Openers of calcium-activated potassium channels and endothelium-dependent hyperpolarizations in the guinea pig carotid artery. | Naunyn-Schmiedeberg's archives of pharmacology 20080401 |
| Selective positive modulation of the SK3 and SK2 subtypes of small conductance Ca2+-activated K+ channels. | British journal of pharmacology 20070701 |
| Formation of cellular projections in neural progenitor cells depends on SK3 channel activity. | Journal of neurochemistry 20070601 |
| Adenosine closes the K+ channel KCa3.1 in human lung mast cells and inhibits their migration via the adenosine A2A receptor. | European journal of immunology 20070601 |
| Calcium and small-conductance calcium-activated potassium channels in gonadotropin-releasing hormone neurons before, during, and after puberty. | Endocrinology 20070501 |
| Inhibition of intermediate-conductance Ca2+-activated K+ channel and cytoprotective properties of 4-piperidinomethyl-2-isopropyl-5-methylphenol. | The Journal of pharmacy and pharmacology 20070501 |
| Ca2+ release-dependent hyperpolarizations modulate the firing pattern of juvenile GABA neurons in mouse substantia nigra pars reticulata in vitro. | The Journal of physiology 20061215 |
| Role of Ca2+-activated K+ channels in duodenal mucosal ion transport and bicarbonate secretion. | American journal of physiology. Gastrointestinal and liver physiology 20061201 |
| Expression of intermediate-conductance, Ca2+-activated K+ channel (KCNN4) in H441 human distal airway epithelial cells. | American journal of physiology. Lung cellular and molecular physiology 20061101 |
| Inhibitory gating modulation of small conductance Ca2+-activated K+ channels by the synthetic compound (R)-N-(benzimidazol-2-yl)-1,2,3,4-tetrahydro-1-naphtylamine (NS8593) reduces afterhyperpolarizing current in hippocampal CA1 neurons. | Molecular pharmacology 20061101 |
| Combination of Ca2+ -activated K+ channel blockers inhibits acetylcholine-evoked nitric oxide release in rat superior mesenteric artery. | British journal of pharmacology 20061101 |
| Exposure to sodium butyrate leads to functional downregulation of calcium-activated potassium channels in human airway epithelial cells. | Pflugers Archiv : European journal of physiology 20061101 |
| Distinct K+ conductive pathways are required for Cl- and K+ secretion across distal colonic epithelium. | American journal of physiology. Cell physiology 20061001 |
| In vivo characterisation of the small-conductance KCa (SK) channel activator 1-ethyl-2-benzimidazolinone (1-EBIO) as a potential anticonvulsant. | European journal of pharmacology 20060928 |
| SK Ca2+-activated K+ channel ligands alter the firing pattern of dopamine-containing neurons in vivo. | Neuroscience 20060630 |
| Impaired small-conductance Ca2+-activated K+ channel-dependent EDHF responses in Type II diabetic ZDF rats. | British journal of pharmacology 20060601 |
| Mechanisms underlying the impaired EDHF-type relaxation response in mesenteric arteries from Otsuka Long-Evans Tokushima Fatty (OLETF) rats. | European journal of pharmacology 20060524 |
| Subtype-specific, bi-component inhibition of SK channels by low internal pH. | Biochemical and biophysical research communications 20060512 |
| Impairment of PAR-2-mediated relaxation system in colonic smooth muscle after intestinal inflammation. | British journal of pharmacology 20060501 |
| Decreases in the precision of Purkinje cell pacemaking cause cerebellar dysfunction and ataxia. | Nature neuroscience 20060301 |
| DCEBIO stimulates Cl- secretion in the mouse jejunum. | American journal of physiology. Cell physiology 20060101 |
| Interactions of N-terminal and C-terminal parts of the small conductance Ca2+ activated K+ channel, hSK3. | Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20060101 |
| Specific enhancement of SK channel activity selectively potentiates the afterhyperpolarizing current I(AHP) and modulates the firing properties of hippocampal pyramidal neurons. | The Journal of biological chemistry 20051216 |
| Activation of SK channels inhibits epileptiform bursting in hippocampal CA3 neurons. | Brain research 20051214 |
| Ion transport regulated by protease-activated receptor 2 in human airway Calu-3 epithelia. | British journal of pharmacology 20051001 |
| Reduced hyperpolarization in endothelial cells of rabbit aortic valve following chronic nitroglycerine administration. | British journal of pharmacology 20051001 |
| 1-Ethyl-2-benzimidazolinone (EBIO) suppresses epileptiform activity in in vitro hippocampus. | Neuropharmacology 20050901 |
| Evidence in favor of a calcium-sensing receptor in arterial endothelial cells: studies with calindol and Calhex 231. | Circulation research 20050819 |
| Cl- secretory effects of EBIO in the rabbit conjunctival epithelium. | American journal of physiology. Cell physiology 20050701 |
| Mediators involved in decreasing peripheral vascular resistance with carbachol in the rat hind limb perfusion model. | Journal of pharmacological sciences 20050701 |
| Beta2-adrenoceptor regulation of the K+ channel iKCa1 in human mast cells. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050601 |
| Impaired EDHF-mediated vasodilation and function of endothelial Ca-activated K channels in uremic rats. | Kidney international 20050601 |
| A functional role for small-conductance calcium-activated potassium channels in sensory pathways including nociceptive processes. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20050406 |
| Genistein stimulates electrogenic Cl(-) secretion in mouse jejunum. | American journal of physiology. Cell physiology 20041201 |
| Reduction of airway anion secretion via CFTR in sphingomyelin pathway. | Biochemical and biophysical research communications 20041112 |
| Activation of human IK and SK Ca2+ -activated K+ channels by NS309 (6,7-dichloro-1H-indole-2,3-dione 3-oxime). | Biochimica et biophysica acta 20041011 |
| A 'virtual gland' method for quantifying epithelial fluid secretion. | American journal of physiology. Lung cellular and molecular physiology 20041001 |
| Regulation of antiprotease and antimicrobial protein secretion by airway submucosal gland serous cells. | The Journal of biological chemistry 20040910 |
| The K+ channel iKCA1 potentiates Ca2+ influx and degranulation in human lung mast cells. | The Journal of allergy and clinical immunology 20040701 |
| Hypoxia-induced inhibition of whole cell membrane currents and ion transport of A549 cells. | American journal of physiology. Lung cellular and molecular physiology 20040601 |
| ATP release triggered by activation of the Ca2+-activated K+ channel in human airway Calu-3 cells. | American journal of respiratory cell and molecular biology 20040301 |
| An apamin- and scyllatoxin-insensitive isoform of the human SK3 channel. | Molecular pharmacology 20040301 |
| Inhibition of endothelium-dependent vasorelaxation by extracellular K(+): a novel controlling signal for vascular contractility. | American journal of physiology. Heart and circulatory physiology 20040101 |
| Calcium and Vitamin D increase mRNA levels for the growth control hIK1 channel in human epidermal keratinocytes but functional channels are not observed. | BMC dermatology 20040101 |
| Tempol, an antioxidant, restores endothelium-derived hyperpolarizing factor-mediated vasodilation during hypertension. | European journal of pharmacology 20031114 |
| Role of endothelial intermediate conductance KCa channels in cerebral EDHF-mediated dilations. | American journal of physiology. Heart and circulatory physiology 20031001 |
| Calcium activates SK channels in the intact human lens. | Investigative ophthalmology & visual science 20030901 |
| Apamin-sensitive small conductance calcium-activated potassium channels, through their selective coupling to voltage-gated calcium channels, are critical determinants of the precision, pace, and pattern of action potential generation in rat subthalamic nucleus neurons in vitro. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20030820 |
| Effects of intermediate-conductance Ca2+-activated K+ channel modulators on human prostate cancer cell proliferation. | European journal of pharmacology 20030627 |
| Modulation of Ca2+-activated Cl- secretion by basolateral K+ channels in human normal and cystic fibrosis airway epithelia. | Pediatric research 20030401 |
| Inhibition of EDHF by two new combinations of K+-channel inhibitors in rat isolated mesenteric arteries. | British journal of pharmacology 20030301 |
| Unexpected down-regulation of the hIK1 Ca2+-activated K+ channel by its opener 1-ethyl-2-benzimidazolinone in HaCaT keratinocytes. Inverse effects on cell growth and proliferation. | The Journal of biological chemistry 20030131 |
| Stimulatory effects of chlorzoxazone, a centrally acting muscle relaxant, on large conductance calcium-activated potassium channels in pituitary GH3 cells. | Brain research 20030103 |
| SK4/IK1-like channels mediate TEA-insensitive, Ca2+-activated K+ currents in bovine parotid acinar cells. | American journal of physiology. Cell physiology 20030101 |
| Expression and activity of potassium ion channels in human prostate cancer. | Cancer letters 20021201 |
| Characterization of a charybdotoxin-sensitive intermediate conductance Ca2+-activated K+ channel in porcine coronary endothelium: relevance to EDHF. | British journal of pharmacology 20021201 |
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| Role for endothelium-derived hyperpolarizing factor in vascular tone in rat mesenteric and hindlimb circulations in vivo. | The Journal of physiology 20020801 |
| Charybdotoxin-sensitive small conductance K(Ca) channel activated by bradykinin and substance P in endothelial cells. | British journal of pharmacology 20020801 |
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| Physiological role of calcium-activated potassium currents in the rat lateral amygdala. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20020301 |
| Characterization of basolateral K+ channels underlying anion secretion in the human airway cell line Calu-3. | The Journal of physiology 20020201 |
| Activation of endothelial cell IK(Ca) with 1-ethyl-2-benzimidazolinone evokes smooth muscle hyperpolarization in rat isolated mesenteric artery. | British journal of pharmacology 20011201 |
| Chlorzoxazone or 1-EBIO increases Na(+) absorption across cystic fibrosis airway epithelial cells. | American journal of physiology. Lung cellular and molecular physiology 20011101 |
| Novel effects of minocycline on Ca(2+)-dependent Cl(-) secretion in human airway epithelial Calu-3 cells. | Toxicology and applied pharmacology 20011015 |
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| Phenanthrolines--a new class of CFTR chloride channel openers. | British journal of pharmacology 20011001 |
| Regulation of anion secretion by nitric oxide in human airway epithelial cells. | American journal of physiology. Lung cellular and molecular physiology 20010801 |
| Comparison of effects of diabetes mellitus on an EDHF-dependent and an EDHF-independent artery. | American journal of physiology. Heart and circulatory physiology 20010701 |
| Microelectrode and impedance analysis of anion secretion in Calu-3 cells. | JOP : Journal of the pancreas 20010701 |
| EDHF is not K+ but may be due to spread of current from the endothelium in guinea pig arterioles. | American journal of physiology. Heart and circulatory physiology 20010601 |
| Pharmacological modulation of SK3 channels. | Neuropharmacology 20010601 |
| Differential expression of the small-conductance, calcium-activated potassium channel SK3 is critical for pacemaker control in dopaminergic midbrain neurons. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20010515 |
| Control of electrical activity in central neurons by modulating the gating of small conductance Ca2+-activated K+ channels. | The Journal of biological chemistry 20010330 |
| NH(2)-terminal modification of a channel-forming peptide increases capacity for epithelial anion secretion. | American journal of physiology. Cell physiology 20010301 |
| Modulation of recombinant small-conductance Ca(2+)-activated K(+) channels by the muscle relaxant chlorzoxazone and structurally related compounds. | The Journal of pharmacology and experimental therapeutics 20010301 |
| Assessment of CFTR chloride channel openers in intact normal and cystic fibrosis murine epithelia. | British journal of pharmacology 20010201 |
| Benzimidazolone activators of chloride secretion: potential therapeutics for cystic fibrosis and chronic obstructive pulmonary disease. | The Journal of pharmacology and experimental therapeutics 20010201 |
| Expression and biological significance of Ca2+-activated ion channels in human keratinocytes. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20010101 |
| Characterisation of the rat SK4/IK1 K(+) channel. | Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20010101 |
| EBIO, an agent causing maintained epithelial chloride secretion by co-ordinate actions at both apical and basolateral membranes. | Pflugers Archiv : European journal of physiology 20010101 |
| Pharmacological activation of cloned intermediate- and small-conductance Ca(2+)-activated K(+) channels. | American journal of physiology. Cell physiology 20000301 |
| Characterization of the cloned human intermediate-conductance Ca2+-activated K+ channel. | The American journal of physiology 19980901 |
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