40172-65-4

Usage

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 
• 17356-08-0 thiourea 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 333-20-0 potassium thioacyanate 
• 134-32-7 1-amino-naphthalene 

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 
• 1119706-72-7 phenyl N-(naphtho[1,2-d]thiazol-2-yl)carbamate 
• 139331-56-9 3-{3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-propyl}-1H-naphtho[2,1-b][1,4]thiazin-2-one 

Relevant academic research and scientific papers

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.

Synthesis and spectral properties of some azo disperse dyes containing a benzothiazole moiety

A known method was employed for the preparation of four substituted benzothiazole amines I-IV in moderate yields. These heterocyclic amines were diazotized with nitorsyl sulfuric acid and subsequently coupled with N,N-diethyl aniline and N-phenyl-2, 2′-iminodiethanol to afford heteroarylazo amine dyes 1-8 in satisfactory yields. These dyes were characterized by UV-Visible, FT-IR, 1H NMR, and elemental analysis techniques. The solvatochromism behavior of the azo compounds is investigated by studying their spectra in pure and mixed organic solvents of different characteristics. The color of the dyes is discussed with respect to the nature of the heterocyclic ring and substituent present therein. In addition, effects of acid and base on the visible absorption maxima of the dyes are also reported.

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.

Synthesis of some novel N4-(naphtha[1,2-d]thiazol-2-yl)semicarbazides as potential anticonvulsants

A series of N4-(naphtha[1,2-d]thiazol-2-yl)semicarbazides were designed and synthesized to meet the structural requirements essential for anticonvulsant activity. Anticonvulsant activity was determined after intraperitoneal (i.p.) administration to mice by maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ)-induced seizure tests and minimal motor impairment was determined by rotorod test. A majority of the compounds exhibited significant anticonvulsant activity after intraperitoneal administration. Some of the selected compounds were evaluated orally in rats for activity in scPTZ test at several time points (50 mg/kg). The most active compounds carry bromo, fluoro and nitro substituents at 4-position in the phenyl ring. The biochemical estimations of malondialdehyde (MDA), superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) from brain homogenate not only clearly implicated the role of free radicals in PTZ-induced convulsion but also explained the possible mechanism of protective effect of semicarbazides, through the reduced formation of MDA and increased formation of SOD and GSH-Px.

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);

Synthesis and biological activities of new 1,4-benzothiazine derivatives

New 2H-1,4-benzothiazin-3(4H)-one derivatives possessing (4-phenyl-1-piperazinyl)alkyl moieties at the 2-position were synthesized and tested for calcium antagonistic and calmodulin antagonistic activities. Antihypertensive effects in spontaneously hypertensive rats were also evaluated. In general, these compounds were rather weak calcium channel blockers, although, in contrast, many of them had moderate to potent calmodulin antagonistic activity, and 2-[3-(4-(4-fluorophenyl)-1-piperazinyl]propyl]-2H-1,4-benzothiazin-3(4H )-one derivatives 45, 74 and 75 showed potent antihypertensive effects.

Substituted 2-aminobenzothiazoles and derivatives useful as cerebrovascular agents

A series of substituted 2-aminobenzothiazoles and derivatives useful for treating cerebrovascular disorders are disclosed. Also disclosed is a new method for treating such disorders.