2-Amino-beta-naphthothiazole

Product Name2-Amino-beta-naphthothiazole
CAS40172-65-4
MFC11H8N2S
MW200.26
EINECS254-822-1
MOL File40172-65-4.mol

Chemical Properties

Melting point	184-188°C
Boiling point	417.1±28.0 °C(Predicted)
Density	1.403±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,2-8°C
solubility	DMSO: ≥30mg/mL
form	solid
pka	3.50±0.30(Predicted)
color	Off-white
Stability	Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
InChI	1S/C11H8N2S/c12-11-13-10-8-4-2-1-3-7(8)5-6-9(10)14-11/h1-6H,(H2,12,13)
InChIKey	FECQXVPRUCCUIL-UHFFFAOYSA-N
SMILES	Nc1nc2c(ccc3ccccc23)s1
CAS DataBase Reference	40172-65-4(CAS DataBase Reference)
EPA Substance Registry System	Naphtho[1,2-d]thiazol-2-amine (40172-65-4)

Safety Information

Hazard Codes	Xn
Risk Statements	20/21/22-36/37/38-36-22
Safety Statements	22-36/37/39-26
WGK Germany	WGK 3
TSCA	TSCA listed
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2

Usage And Synthesis

Description

SKA-31 (40172-65-4) is a KCa3.1 and KCa2 potassium channel activator (EC50 =260, 2900, 2900 nM for KCa3.1, KCa2.1 and KCa2.2 respectively). Enhanced acetylcholine-induced EDHF dilator response in mouse carotid arteries and lowers blood pressure in mouse models at 30 mg/Kg.1,2 Evokes robust vasodilation in rat mesenteric arteries.3

Uses

SKA-31 is a potent potassium channel activator with EC50s of 260 nM, 1.9 μM, 2.9 μM, and 2.9 μM for KCa3.1, KCa2.2, KCa2.1 and KCa2.3, respectively. SKA-31 potentiates endothelium-derived hyperpolarizing factor response and lowers blood pressure[1].

Biological Activity

Activator of K Ca 3.1 and K Ca 2 channels (EC 50 values are 260, 2900, 2900 nM for K Ca 3.1, K Ca 2.1 and K Ca 2.2 respectively). Potentiates acetylcholine-induced EDHF-type dilations of mouse carotid arteries and lowers blood pressure in normotensive and hypertensive mice.

in vivo

SKA-31 is not acutely toxic and has good pharmacokinetic properties^[1].
SKA-31 potentiates native KCa3.1 and KCa2.3 in murine carotid endothelium with EC₅₀ values of 225 nM and 1.6 μM for KCa3.1 and KCa2.3, respectively^[1].
SKA-31 stimulates KCa3.1 and KCa2.3 in vascular endothelial cells and increases acetylcholine-induced endothelium-derived hyperpolarizing factor (EDHF) -mediated vasodilation^[1].
SKA-31 potentiates EDHF-type vasodilations and lowers blood pressure in mice. Injections of SKA-31 (1-30 mg/kg; i.p.) lower MAP over 24 hours in normotensive wild-type mice but not in KCa3.1(-/-) mice (-/-)^[1].

Animal Model:	16-25 weeks mice^[1]
Dosage:	1 mg/kg, 10 mg/kg, and 30 mg/kg
Administration:	Intraperitoneal injection
Result:	Lower MAP over 24 hours in normotensive wild-type mice but not in KCa3.1(-/-) mice (-/-).

storage

+4°C

References

[1] ANANTHAKRISHNAN SANKARANARAYANAN. Naphtho[1,2-d]thiazol-2-ylamine (SKA-31), a new activator of KCa2 and KCa3.1 potassium channels, potentiates the endothelium-derived hyperpolarizing factor response and lowers blood pressure.[J]. Molecular Pharmacology, 2009, 75 2: 281-295. DOI:10.1124/mol.108.051425
[2] SEBASTIAN BRÄHLER. Genetic deficit of SK3 and IK1 channels disrupts the endothelium-derived hyperpolarizing factor vasodilator pathway and causes hypertension.[J]. Circulation, 2009, 119 17: 2323-2332. DOI:10.1161/circulationaha.108.846634
[3] RAYAN KHADDAJ-MALLAT Andrew P B Cini Mathew John. SKA-31, an activator of endothelial Ca2+-activated K+ channels evokes robust vasodilation in rat mesenteric arteries[J]. European journal of pharmacology, 2018, 831: Pages 60-67. DOI:10.1016/j.ejphar.2018.05.006

2-Amino-beta-naphthothiazole

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