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

Basic information Safety Supplier Related

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

Product Name:
3-[(5-CHLORO-2-HYDROXYPHENYL)METHYL]-5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOL-2(3H)-ONE
Synonyms:
  • 3-[(5-CHLORO-2-HYDROXYPHENYL)METHYL]-5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOL-2(3H)-ONE
  • BMS 191011
  • 3-(5-chloro-2-hydroxybenzyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one
  • 3-(5-chloro-2-hydroxybenzyl)-5-(4-(trifluoroMethyl)phenyl)-1,3,4
  • 3-(5-Chloro-2-hydroxybenzyl)
  • -5-(4-(trifluoromethyl)
  • BMS-A
  • 1,3,4-Oxadiazol-2(3H)-one, 3-[(5-chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-
CAS:
202821-81-6
MF:
C16H10ClF3N2O3
MW:
370.71
Mol File:
202821-81-6.mol
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3-[(5-CHLORO-2-HYDROXYPHENYL)METHYL]-5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOL-2(3H)-ONE Chemical Properties

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)
pka
9.27±0.43(Predicted)
form 
powder
color 
white to beige
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Safety Information

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
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3-[(5-CHLORO-2-HYDROXYPHENYL)METHYL]-5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOL-2(3H)-ONE Usage And Synthesis

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

Room temperature

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.

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

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