BAY 38-7271 - CAS 212188-60-8
Catalog number: 212188-60-8
Category: Inhibitor
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Molecular Formula:
C20H21F3O5S
Molecular Weight:
430.44
COA:
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Targets:
Cannabinoid Receptor
Description:
BAY 38-7271, also called as KN 38-7271, is a cannabinoid receptor agonist with analgesic and neuroprotective effects. The doses of BAY 38-7271 in animals needed for maximal neuroprotective efficacy were significantly lower than those inducing typical cannabinoid-like side effects.
Purity:
>98%
Appearance:
Solid powder
Synonyms:
[3-[[(2R)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-4-yl]oxy]phenyl] 4,4,4-trifluorobutane-1-sulfonate; 3-(2-hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate; BAY-38-7271; BAY387271; BAY 38-7271; UNII-SRX4T6TMUS; (-)-Bay-38-7271;
MSDS:
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Boiling Point:
459.0±40.0ºC at 760 mmHg
Density:
1.6±0.1 g/cm3
InChIKey:
XJURALZPEJKKOV-CQSZACIVSA-N
InChI:
1S/C20H21F3O5S/c21-20(22,23)8-3-9-29(25,26)28-17-6-2-5-16(12-17)27-19-7-1-4-15-10-14(13-24)11-18(15)19/h1-2,4-7,12,14,24H,3,8-11,13H2/t14-/m1/s1
Canonical SMILES:
C1C(CC2=C1C=CC=C2OC3=CC(=CC=C3)OS(=O)(=O)CCCC(F)(F)F)CO
1.Characterization of the diarylether sulfonylester (-)-(R)-3-(2-hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) as a potent cannabinoid receptor agonist with neuroprotective properties.
Mauler F1, Mittendorf J, Horváth E, De Vry J. J Pharmacol Exp Ther. 2002 Jul;302(1):359-68.
(-)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) is a new high-affinity cannabinoid receptor subtype 1 (CB1 receptor) ligand (K(i) = 0.46-1.85 nM; rat brain, human cortex, or recombinant human CB1 receptor), structurally unrelated to any cannabinoid receptor ligand known so far. BAY 38-7271 was characterized as a CB1 receptor agonist in 5-[gamma(35)S]-thiophosphate triethylammonium salt binding assays using rat or human CB1 receptors. In the rat hypothermia assay, BAY 38-7271 induced a dose-dependent reduction in body temperature (minimal effective dose = 6 microg/kg, i.v.); whereas in rats trained to discriminate the CB1/CB2 receptor agonist (-)-cis-3-[2-hydroxy-4(1,1-dimethyl-heptyl)phenyl]-trans-4-(3-hydroxypropyl) cyclohexanol (CP 55,940; 0.03 mg/kg, i.p.) from vehicle, BAY 38-7271 induced complete generalization (3 microg/kg, i.v.). In both in vivo models, a specific CB1 receptor-mediated mechanism was confirmed by demonstrating that the effects of CP 55,940 and BAY 38-7271 were blocked by pretreatment with the selective CB1 receptor antagonist N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamidehydrochloride.
2.Cannabinoid receptor subtypes 1 and 2 mediate long-lasting neuroprotection and improve motor behavior deficits after transient focal cerebral ischemia.
Schmidt W1, Schäfer F, Striggow V, Fröhlich K, Striggow F. Neuroscience. 2012 Dec 27;227:313-26. doi: 10.1016/j.neuroscience.2012.09.080. Epub 2012 Oct 13.
The endocannabinoid system is crucially involved in the regulation of brain activity and inflammation. We have investigated the localization of cannabinoid CB1 and CB2 receptors in adult rat brains before and after focal cerebral ischemia due to endothelin-induced transient occlusion of the middle cerebral artery (eMCAO). Using immunohistochemistry, both receptor subtypes were identified in cortical neurons. After eMCAO, neuronal cell death was accompanied by reduced neuronal CB1 and CB2 receptor-linked immunofluorescence. In parallel, CB1 receptor was found in activated microglia/macrophages 3 days post eMCAO and in astroglia cells at days 3 and 7. CB2 receptor labeling was identified in activated microglia/macrophages or astroglia 3 and 7d ays post ischemia, respectively. In addition, immune competent CD45-positive cells were characterized by pronounced CB2 receptor staining 3 and 7 days post eMCAO. KN38-72717, a potent and selective CB1 and CB2 receptor agonist, revealed a significant, dose-dependent and long-lasting reduction of cortical lesion sizes due to eMCAO, when applied consecutively before, during and after eMCAO.
3.Discriminative stimulus effects of the structurally novel cannabinoid CB1/CB2 receptor partial agonist BAY 59-3074 in the rat.
De Vry J1, Jentzsch KR. Eur J Pharmacol. 2004 Nov 28;505(1-3):127-33.
BAY 59-3074 [3-[2-cyano-3-(trifluoromethyl)phenoxy]phenyl-4,4,4-trifluoro-1-butane-sulfonate] is a structurally novel cannabinoid CB1/CB2 receptor partial agonist with analgesic properties. The present study was performed to confirm its receptor binding profile in a highly sensitive in vivo assay. Rats (n=10) learned to discriminate BAY 59-3074 (0.5 mg/kg, p.o., t-1 h) from vehicle in a fixed-ratio: 10, food-reinforced two-lever procedure after a median number of 28 training sessions. BAY 59-3074 generalized dose-dependently (ED(50): 0.081 mg/kg, p.o.) and the cue was detectable between 0.25 and 4 h after administration. The selective cannabinoid CB1 receptor antagonist SR 141716A [N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochloride] blocked the discriminative effects of BAY 59-3074 (ID50: 1.79 mg/kg, i.p.). Complete generalization was also obtained after i.p. administration of BAY 59-3074 (ED50 value: 0.
4.Neuroprotective and brain edema-reducing efficacy of the novel cannabinoid receptor agonist BAY 38-7271.
Mauler F1, Hinz V, Augstein KH, Fassbender M, Horváth E. Brain Res. 2003 Oct 31;989(1):99-111.
BAY 38-7271 is a new high-affinity cannabinoid receptor agonist with strong neuroprotective efficacy in a rat model of traumatic brain injury (acute subdural hematoma, SDH). In the present study we investigated CB1 receptor signal transduction by [35S]GTPgammaS binding in situ and in vitro to assess changes in receptor functionality after SDH. Further, we continued to investigate the neuroprotective properties of BAY 38-7271 in the rat SDH and transient middle cerebral artery occlusion (tMCA-O) model as well as the efficacy with respect to SDH-induced brain edema. [35S]GTPgammaS binding revealed minor attenuation of CB1 receptor functionality on brain membranes from injured hemispheres when compared to non-injured hemispheres or controls. In the rat SDH model, BAY 38-7271 displayed strong neuroprotective efficacy when administered immediately after SDH either as a 1 h (65% infarct volume reduction at 0.1 microg/kg) or short-duration (15 min) infusion (53% at 10 microg/kg).
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CAS 212188-60-8 BAY 38-7271

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