50850-92-5

Usage

Uses

Used in Pharmaceutical Industry:
6-(methylthio)benzothiazol-2-amine is used as a pharmaceutical agent for its ability to modulate sodium flux as an inhibitor. This property makes it a potential candidate for the development of drugs targeting ion channels and transporters, which play crucial roles in various physiological and pathological processes.
Used in Chemical Research:
6-(methylthio)benzothiazol-2-amine can also be used as a research compound in chemical and medicinal chemistry. It can be employed to study the structure-activity relationships of benzothiazolamine derivatives and to develop new compounds with improved biological activities and selectivity.
Used in Material Science:
Due to its unique chemical structure, 6-(methylthio)benzothiazol-2-amine may also find applications in material science, particularly in the development of new materials with specific properties, such as conductivity, stability, or sensing capabilities.

InChI:InChI=1/C8H8N2S2/c1-11-5-2-3-6-7(4-5)12-8(9)10-6/h2-4H,1H3,(H2,9,10)

Upstream product

• 65069-54-7 1-(4-(methylthio)phenyl)thiourea 
• 540-72-7 sodium thiocyanide 
• 104-96-1 4-methylsulfanylaniline 
• 1849-36-1 para-nitrobenzenethiol 
• 333-20-0 potassium thioacyanate 
• 701-57-5 1-methylthio-4-nitro-benzene 

Downstream Products

• 100601-18-1 2-amino-5-(methylthio)benzenethiol 
• 207225-21-6 6-thiomethylbenzothiazole 
• 17557-67-4 2-amino-6-(methylsulfonyl)benzothiazole 
• 1314518-75-6 C₅₄H₅₄B₂F₄N₆O₂S₄ 
• 1314518-68-7 C₅₄H₅₆N₆O₂S₄ 

Relevant academic research and scientific papers

Enhancement of Benzothiazoles as Pteridine Reductase-1 Inhibitors for the Treatment of Trypanosomatidic Infections

2-Amino-benzo[d]thiazole was identified as a new scaffold for the development of improved pteridine reductase-1 (PTR1) inhibitors and anti-trypanosomatidic agents. Molecular docking and crystallography guided the design and synthesis of 42 new benzothiazoles. The compounds were assessed for Trypanosoma brucei and Leishmania major PTR1 inhibition and in vitro activity against T. brucei and amastigote Leishmania infantum. We identified several 2-amino-benzo[d]thiazoles with improved enzymatic activity (TbPTR1 IC50 = 0.35 μM; LmPTR1 IC50 = 1.9 μM) and low μM antiparasitic activity against T. brucei. The ten most active compounds against TbPTR1 were able to potentiate the antiparasitic activity of methotrexate when evaluated in combination against T. brucei, with a potentiating index between 1.2 and 2.7. The compound library was profiled for early ADME toxicity, and 2-amino-N-benzylbenzo[d]thiazole-6-carboxamide (4c) was finally identified as a novel potent, safe, and selective anti-trypanocydal agent (EC50 = 7.0 μM). Formulation of 4c with hydroxypropyl-β-cyclodextrin yielded good oral bioavailability, encouraging progression to in vivo studies.

Pyrrolopyrrole cyanines: Effect of substituents on optical properties

To tune their optical properties, a large variety of pyrrolopyrrole cyanines (PPCys) were synthesized with substitutedheteroaromatics such as quinoline, benzothiazole, and oxazole derivatives as terminal groups. Thus, a broad range of stable, highly fluorescing near-infrared (NIR) dyes with high absorptivities between 690 to 845 nm is accessible. The large number of newly synthesized compounds allows a detailed discussion of the correlation between molecular structure and the optical properties of the first electronic transition. Syntheses and optical properties of pyrrolopyrrole cyanines (PPCys) with different substituents at the terminal heteroaromatic moieties are described. The relationship between molecular structure and optical properties is discussed. By suitable substitution, the absorption and fluorescence maxima of the chromophore can be tuned in a range between 690 and 845 nm. Copyright

Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives

A series of novel thiazole-containing triazole antifungals was synthesized and evaluated for antifungal activity against a variety of clinically isolated pathogenic fungi in vitro and against systemic candidosis in vivo. These compounds showed potent antifungal activities in vitro and in vivo. In particular, (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4- difluorophenyl)-1-(1H-1,2,4-triazol-l-yl)-2-butanol (12g; ER-30346) showed potent and well-balanced in vitro activities and potent in vivo efficacy, and had a good safety profile.

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.