326-45-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-6-(trifluoromethylsulfanyl)benzothiazole is used as a therapeutic agent for its potential biological activities. Given the diverse applications of benzothiazoles in medicine, 2-Amino-6-(trifluoro-methylsufanyl)benzothiazole may be employed in the development of new drugs or as a component in existing pharmaceutical formulations. Its specific role in pharmaceuticals could be related to its chemical structure, which may confer unique properties that are beneficial for therapeutic purposes.
Used in Research and Development:
2-Amino-6-(trifluoromethylsulfanyl)benzothiazole is used as a research compound for studying its chemical properties and potential interactions with biological systems. In academic and industrial research settings, 2-Amino-6-(trifluoro-methylsufanyl)benzothiazole may be utilized to investigate its effects on various biological processes, which could lead to the discovery of new applications or insights into its mechanism of action.

Upstream product

• 372-16-7 thioorthocarbonotrifluoridic acid 4-amino-phenyl ester 
• 1147550-11-5 ammonium thiocyanate 
• 333-20-0 potassium thioacyanate 
• 100-01-6 4-nitro-aniline 
• 1849-36-1 para-nitrobenzenethiol 
• 403-66-7 p-nitrophenyl trifluoromethyl sulfide 

Downstream Products

• 3771-52-6 N,N-dimethyl-4-(6-trifluoromethylsulfanyl-benzothiazol-2-ylazo)-aniline 
• 2414-49-5 2,2'-[3-trifluoromethyl-4-(6-trifluoromethylsulfanyl-benzothiazol-2-ylazo)-phenylazanediyl]-bis-ethanol 
• 2193-91-1 2,2'-[3-methyl-4-(6-trifluoromethylsulfanyl-benzothiazol-2-ylazo)-phenylazanediyl]-bis-ethanol 

Relevant academic research and scientific papers

Chalcogen OCF3 Isosteres Modulate Drug Properties without Introducing Inherent Liabilities

The synthesis of SCF3 as well as SeCF3 isosteres of two OCF3-containing drugs was achieved through visible light and copper-catalyzed processes. Herein, we show that chalcogen replacement modulates physicochemical and ADME properties without introducing intrinsic liabilities. The SCF3 and SeCF3 groups are more lipophilic than their oxygen counterpart; however, microsomal stability is unchanged, indicating that these molecular changes may be beneficial for in vivo half-life. Enabled by modern synthetic methods, we present the chalcogen-CF3 groups as potential key players for future fluorinated pharmaceuticals.

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.

Riluzole series. synthesis and in vivo 'antiglutamate' activity of 6- substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines

Two series of analogues of riluzole, a blocker of excitatory amino acid mediated neurotransmission, have been synthesized: monosubstituted 2- benzothiazolamines and 3-substituted derivatives. Of all the compounds prepared in the first series, only 2-benzothiazolamines bearing alkyl, polyfluoroalkyl, or polyfluoroalkoxy substituents in the 6-position showed potent anticonvulsant activity against administration of glutamic acid in rats. The most active compounds displaying in vivo 'antiglutamate' activity were the 6-OCF3 (riluzole), 6-OCF2CF3, 6-CF3, and 6-CF2CF3 substituted derivatives with ED50 values between 2.5 and 3.2 mg/kg i.p. Among the second series of variously substituted benzothiazolines, compounds as active as riluzole or up to 3 times more potent were identified in two series: benzothiazolines bearing a β-dialkylaminoethyl moiety and compounds with an alkylthioalkyl chain and their corresponding sulfoxides and sulfones. The most potent derivatives were 2-imino-3-(2-methylthio)- and 2-imino-3-(2- methylsulfinyl)-ethyl-6-trifluoromethoxybenzothiazolines (61 and 64, ED50 = 1.0 and 1.1 mg/kg i.p., respectively). In addition, intraperitoneal administration of some of the best benzothiazolines protected mice from mortality produced by hypobaric hypoxia.