40172-65-4

Basic information

• Product Name: 2-AMINO-BETA-NAPHTHOTHIAZOLE
• Synonyms: NAPHTHO[1,2-D][1,3]THIAZOL-2-AMINE;NAPHTHO[1,2-D]THIAZOL-2-YLAMINE;2-AMINO-BETA-NAPHTHOTHIAZOLE;2-AMINO-NAPHTHO[1,2-D]THIAZOLE;2-AMINONAPHTHO-1,2-THIAZOLE;AKOS BBS-00006561;IFLAB-BB F1386-0401;LABOTEST-BB LT00154570
• CAS NO: 40172-65-4
• Molecular Formula: C₁₁H₈N₂S
• Molecular Weight: 200.26
• EINECS: 254-822-1
• Product Categories: BENZOTHIAZOLE
• Mol File: 40172-65-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 184-188°C
• Boiling Point: 417.1°C at 760 mmHg
• Flash Point: 206.1°C
• Appearance: /
• Density: 1.403g/cm³
• Vapor Pressure: 3.63E-07mmHg at 25°C
• Refractive Index: 1.83
• Storage Temp.: Store at +4°C
• Solubility: DMSO: ≥30mg/mL
• PKA: 3.50±0.30(Predicted)
• Stability: Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: 2-AMINO-BETA-NAPHTHOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-BETA-NAPHTHOTHIAZOLE(40172-65-4)
• EPA Substance Registry System: 2-AMINO-BETA-NAPHTHOTHIAZOLE(40172-65-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-36-22
• Safety Statements: 22-36/37/39-26
• Hazardous Substances Data: 40172-65-4(Hazardous Substances Data)

Usage

Description

2-AMINO-BETA-NAPHTHOTHIAZOLE, also known as SKA-31 (40172-65-4), is a compound that acts as a KCa3.1 and KCa2 potassium channel activator. It has demonstrated the ability to enhance acetylcholine-induced EDHF dilator response in mouse carotid arteries and effectively lower blood pressure in mouse models at a dosage of 30 mg/Kg. Additionally, it has been shown to evoke robust vasodilation in rat mesenteric arteries.

Uses

Used in Pharmaceutical Industry:
2-AMINO-BETA-NAPHTHOTHIAZOLE is used as a potassium channel activator for its ability to enhance acetylcholine-induced EDHF dilator response and lower blood pressure in mouse models. This makes it a potential candidate for the development of treatments for hypertension and other cardiovascular conditions.
Used in Research Applications:
In the field of research, 2-AMINO-BETA-NAPHTHOTHIAZOLE is used as a tool to study the function and regulation of KCa3.1 and KCa2 potassium channels. Its ability to activate these channels can provide valuable insights into their role in various physiological processes and potential therapeutic applications.
Used in Drug Development:
2-AMINO-BETA-NAPHTHOTHIAZOLE's robust vasodilation effects in rat mesenteric arteries make it a promising compound for the development of new drugs targeting vascular health and related conditions. Its potential use in this area could lead to the creation of novel treatments for a range of vascular diseases.

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.

References

Sankaranaravanan et al. (2009), 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; Mol. Pharmacol., 75 281 Brahler et al. (2009), Genetic deficit of SK3 and IK1 channels disrupts the endothelium-derived hyperpolarizing factor vasodilator and causes hypertension ; Circulation, 119 2323 Khaddaj-Mallat al. (2018), SKA-31, an activator of endothelial Ca2+-activated K+ channels evokes robust vasodilation in rat mesenteric arteries; Eur. J. Pharmacol., 831 60

InChI:InChI=1/C11H8N2S/c12-11-13-10-8-4-2-1-3-7(8)5-6-9(10)14-11/h1-6H,(H2,12,13)

Upstream product

• 1240-37-5 N,N'-bis(1-naphthyl)thiourea 
• 13207-48-2 1-naphthylthiosemicarbazide 
• 86-88-4 naphthalen-1-yl-thiourea 
• 34176-49-3 2-aminobenzo-4,5-dihydrobenzothiazole 
• 134-32-7 1-amino-naphthalene 
• 17356-08-0 thiourea 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 96400-96-3 2-(p-Dimethylaminobenzylideneamino)naphtho<1,2-d>thiazole 
• 56921-79-0 9-(4-chloro-phenyl)-imidazo[2,1-b]naphtho[1,2-d]thiazole 
• 71856-64-9 11-phenyl-naphtho[1',2':4,5]thiazolo[3,2-a]pyrimidin-9-one 
• 56921-77-8 9-(4-ethoxy-phenyl)-naphtho[1,2-d]imidazo[2,1-b]thiazole 
• 56921-78-9 9-(4-methoxy-phenyl)-naphtho[1,2-d]imidazo[2,1-b]thiazole 
• 84038-92-6 2-Phenyl-4-oxo-naphtho<1,2-d>thiazolo<3,2-a>pyrimidin 
• 94123-42-9 2,3-Diaminonaphto<1,2-d>thiazolium Mesitylenesulfonate 
• 86384-62-5 1-benzoil-3-(nafto<1,2-d>tiazol-2-il)tiourea 
• 86384-63-6 1-fenil-3-(nafto<1,2-d>tiazol-2-il)tiourea 
• 63512-54-9 1-aminonaphthalene-2-thiol 
• 16942-72-6 2-Hydrazinonaphtho<1,2-d>thiazole 

Relevant articles and documents

Structure determination from powder X-ray diffraction data of black azo (hydrazone) pigments

Crystal structures of two black monoazo (hydrazone) pigments have been determined from powder X-ray diffraction data combined with DFT calculations. The DFT calculations suggested the molecules are in hydrazone forms but not in azo forms in both crystal structures. The molecular arrangements in the crystal structures suggested Davydov splitting may occur by excitonic interactions and it causes the red absorption band shift in the crystalline state leading to the characteristic black colors.

Metal-free synthesis of 2-aminobenzothiazoles via aerobic oxidative cyclization/dehydrogenation of cyclohexanones and thioureas

A metal-free process for the synthesis of 2-aminobenzothiazoles from cyclohexanones and thioureas has been developed using catalytic iodine and molecular oxygen as the oxidant under mild conditions. Various 2-aminobenzothiazoles, 2-aminonaphtho[2,1-d]thiazoles, and 2-aminonaphtho[1,2-d] thiazoles were prepared via this method in satisfactory yields.

MONOAZO COMPOUND AND METHOD FOR PRODUCING SAME

The present invention provides a monoazo compound represented by formula (1) or a salt thereof: wherein, Y1 and Y2 represent a group selected from hydrogen atom, formula (2) and formula (3); ????????-CO-E-X?????(3) provided that at least one of Y1 and Y2 is a group represented by formula (2); Z is a group selected from formulae (4), (5) and (6);