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202821-81-6

202821-81-6 Structure

202821-81-6 Structure
IdentificationBack Directory
[Name]

3-[(5-CHLORO-2-HYDROXYPHENYL)METHYL]-5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOL-2(3H)-ONE
[CAS]

202821-81-6
[Synonyms]

BMS-A
BMS 191011
-5-(4-(trifluoromethyl)
BMS-191011 >=98% (HPLC)
3-(5-Chloro-2-hydroxybenzyl)
3-(5-chloro-2-hydroxybenzyl)-5-(4-(trifluoroMethyl)phenyl)-1,3,4
3-(5-chloro-2-hydroxybenzyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one
3-[(5-CHLORO-2-HYDROXYPHENYL)METHYL]-5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOL-2(3H)-ONE
1,3,4-Oxadiazol-2(3H)-one, 3-[(5-chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-
[Molecular Formula]

C16H10ClF3N2O3
[MDL Number]

MFCD09753285
[MOL File]

202821-81-6.mol
[Molecular Weight]

370.71
Chemical PropertiesBack Directory
[Boiling point ]

444.0±55.0 °C(Predicted)
[density ]

1.51±0.1 g/cm3(Predicted)
[storage temp. ]

Store at RT
[solubility ]

DMSO: soluble20mg/mL, clear (warmed)
[form ]

powder
[pka]

9.27±0.43(Predicted)
[color ]

white to beige
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

25
[Safety Statements ]

45
[RIDADR ]

UN 2811 6.1 / PGIII
[WGK Germany ]

3
Hazard InformationBack Directory
[Description]

BMS 191011 is an activator of large-conductance calcium-activated potassium (KCa1.1/BK) channels that increases maximum potassium current to 126% of control in X. laevis oocytes expressing human KCa1.1 channels when used at a concentration of 1 μM. In vivo, BMS 191011 (10-100 μg/kg, i.v.) increases the diameter of retinal arterioles without affecting blood pressure or heart rate in rats, an effect that is reversed by the KCa1.1 channel blocker iberiotoxin .
[Uses]

BMS 191011, is a potent opener of the large-conductance, Ca2+-activated potassium (maxi-K) channel. It has also shown neuroprotective properties in two distinct animal models of stroke- MCAO in the SHR rat and a normotensive model of focal stroke.
[Definition]

ChEBI:3-[(5-chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-one is a member of (trifluoromethyl)benzenes.
[Biological Activity]

Potent Maxi-K channel opener (large-conductance Ca 2+ -activated potassium channel, K Ca 1.1, BK Ca ). Neuroprotectant in two distinct animal models of stroke (MCAO in the SHR rat and a normotensive model of focal stroke).
[storage]

Store at RT
[References]

[1]. hewawasam p, ding m, chen n, et al. synthesis of water-soluble prodrugs of bms-191011: a maxi-k channel opener targeted for post-stroke neuroprotection. bioorganic & medicinal chemistry letters, 2003, 13(10): 1695-1698.
[2]. valverde ma, rojas p, amigo j, et al. acute activation of maxi-k channels (hslo) by estradiol binding to the β subunit. science, 1999, 285(5435): 1929-1931.
[3]. zhang y, bonnan a, bony g, et al. dendritic channelopathies contribute to neocortical and sensory hyperexcitability in fmr1-/y mice. nature neuroscience, 2014, 17(12): 1701-1709.
[4]. gu xq, pamenter me, siemen d, et al. mitochondrial but not plasmalemmal bk channels are hypoxia-sensitive in human glioma. glia, 2014, 62(4): 504-513.
[5]. mori a, suzuki s, sakamoto k, et al. bms-191011, an opener of large-conductance ca2+-activated potassium channels, dilates rat retinal arterioles in vivo. biological and pharmaceutical bulletin, 2011, 34(1): 150-152.
[6]. romine jl, martin sw, meanwell na, et al. 3-[(5-chloro-2-hydroxyphenyl) methyl]-5-[4-(trifluoromethyl) phenyl]-1, 3, 4-oxadiazol-2 (3 h)-one, bms-191011: opener of large-conductance ca2+-activated potassium (maxi-k) channels, identification, solubility, and sar. journal of medicinal chemistry, 2007, 50(3): 528-542.
Spectrum DetailBack Directory
[Spectrum Detail]

3-[(5-CHLORO-2-HYDROXYPHENYL)METHYL]-5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOL-2(3H)-ONE(202821-81-6)1HNMR
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