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SML2333

Sigma-Aldrich

VU0463271

≥98% (HPLC)

Synonyme(s) :

N-Cyclopropyl-N-(4-methyl-2-thiazolyl)-2-[(6-phenyl-3-pyridazinyl)thio]-acetamide, N-Cyclopropyl-N-(4-methyl-2-thiazolyl)-2-[(6-phenyl-3-pyridazinyl)thio]acetamide, N-Cyclopropyl-N-(4-methylthiazol-2-yl)-2-(6-phenylpyridazin-3-ylthio)acetamide

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About This Item

Formule empirique (notation de Hill):
C19H18N4OS2
Numéro CAS:
1391737-01-1
Poids moléculaire :
382.50
Numéro MDL:
MFCD30182240
Code UNSPSC :
12352200

Pureté

≥98% (HPLC)

Forme

powder

Couleur

off-white to blue-gray

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

InChI

1S/C19H18N4OS2/c1-13-11-26-19(20-13)23(15-7-8-15)18(24)12-25-17-10-9-16(21-22-17)14-5-3-2-4-6-14/h2-6,9-11,15H,7-8,12H2,1H3

Clé InChI

DPONSKCACOZTGN-UHFFFAOYSA-N

Actions biochimiques/physiologiques

VU0463271 is a potent and selective potassium-chloride cotransporter 2 (KCC2) inhibitor that displays greatly enhanced potency than its structural analogs VU0255011 (ML077) & VU0240511 (IC50 = 61, 537, and 568 nM, respectively). VU0463271 exhibits much reduced efficacy against the related Na-K-2Cl cotransporter 1 (NKCC1 inhibition max ~37% at 100 μM) and little affinity toward a panel of 68 GPCRs, ion channels, and transporters. Although VU0463271 is reported to exhibit affinity toward mitochondrial translocator protein TSPO (IC50 of 204 nM against PK11195 binding; rat heart) and inhibitory potency against α1B adrenergic receptor (IC50 of 364.7 nM; human α1B CHO transfectants), these proteins are not known to affect chloride homeostasis.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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D Subramanian et al.
Translational psychiatry, 8(1), 16-16 (2018-01-11)
Autism spectrum disorder (ASD) and temporal lobe epilepsy exhibit remarkable comorbidity, but for reasons not clearly understood. To reveal a common pathophysiological mechanism, we here describe and characterize an in vitro epileptiform activity in the rat hippocampus that exhibits common
Hannah Alfonsa et al.
Nature communications, 7, 13495-13495 (2016-11-18)
Chloride regulation affects brain function in many ways, for instance, by dictating the GABAergic reversal potential, and thereby influencing neuronal excitability and spike timing. Consistent with this, there is increasing evidence implicating chloride in a range of neurological conditions. Investigations
Matthew R Kelley et al.
Neuropharmacology, 108, 103-110 (2016-04-26)
Impaired neuronal inhibition has long been associated with the increased probability of seizure occurrence and heightened seizure severity. Fast synaptic inhibition in the brain is primarily mediated by the type A γ-aminobutyric acid receptors (GABAARs), ligand-gated ion channels that can
Peter M Klein et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 38(5), 1232-1248 (2017-12-24)
Maintenance of a low intracellular Cl- concentration ([Cl-]i) is critical for enabling inhibitory neuronal responses to GABAA receptor-mediated signaling. Cl- transporters, including KCC2, and extracellular impermeant anions ([A]o) of the extracellular matrix are both proposed to be important regulators of
Eric Delpire et al.
Bioorganic & medicinal chemistry letters, 22(14), 4532-4535 (2012-06-26)
Further chemical optimization of the MLSCN/MLPCN probe ML077 (KCC2 IC(50)=537 nM) proved to be challenging as the effort was characterized by steep SAR. However, a multi-dimensional iterative parallel synthesis approach proved productive. Herein we report the discovery and SAR of
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