133840-98-9

Usage

Uses

Used in Chemical Synthesis:
6-(TRIFLUOROMETHOXY)-2(3H)-BENZOTHIAZOLONE HYDRAZONE is used as an intermediate or building block in the synthesis of more complex organic compounds for various applications, such as pharmaceuticals, agrochemicals, or materials science.
Used in Research and Development:
6-(TRIFLUOROMETHOXY)-2(3H)-BENZOTHIAZOLONE HYDRAZONE is used as a research compound in academic and industrial laboratories to study its chemical properties, reactivity, and potential applications in different fields.
Used in Pharmaceutical Industry:
6-(TRIFLUOROMETHOXY)-2(3H)-BENZOTHIAZOLONE HYDRAZONE is used as a potential drug candidate or a component in the development of new therapeutic agents, given its unique chemical structure and potential biological activities.
Used in Material Science:
6-(TRIFLUOROMETHOXY)-2(3H)-BENZOTHIAZOLONE HYDRAZONE is used as a component in the development of new materials with specific properties, such as improved stability, reactivity, or other characteristics relevant to material applications.
Used in Agrochemical Industry:
6-(TRIFLUOROMETHOXY)-2(3H)-BENZOTHIAZOLONE HYDRAZONE is used as a potential active ingredient in the development of new agrochemical products, such as pesticides or herbicides, due to its unique chemical structure and potential biological activities.

Upstream product

• 14011-37-1 hydrazine dihydrochloride 
• 1744-22-5 Riluzole 
• 461-82-5 4-(trifluoromethoxy)aniline 

Downstream Products

• 1744-22-5 Riluzole 
• 133840-97-8 2-methylamino-6-trifluoromethoxy-benzothiazole 
• 235101-85-6 SKA-5 
• 133840-96-7 2-chloro-6-(trifluoromethoxy)benzothiazole 

Relevant academic research and scientific papers

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

Synthesis, crystal structure, and antinociceptive effects of some new riluzole derivatives

Nine N-alkylated derivatives of riluzole were synthesized in order to obtain new compounds with potential antinociceptive activity. Riluzole was firstly transformed into (6-trifluoromethoxy-benzothiazol-2-yl)-hydrazine, then it was chlorinated by SOCl2 to obtain 2-chloro-6-trifluoromethoxy-benzothiazole. This intermediate product was treated with nine alkylamines to give N-alkylated derivatives of riluzole respectively. The structures of compounds were confirmed by means of elemental analysis, IR, 1H NMR, and 13C NMR. The synthetic route was optimized and four novel crystals were obtained by recrystallization. This study investigated the antinociceptive activity of some N-alkylated derivatives of riluzole by hot plate test in mice. The relationship between antinociceptive activity and the doses of 4b, 4c, 4h, 4g, and riluzole had been studied. Compared with the control group (0 mg/kg), the effects of compounds 4b and 4h showed a significant increase (13.78 ± 2.89 s, 12.89 ± 2.94 s, respectively). Compound 4c showed extreme significant increase (18.07 ± 3.08 s) in the time mice spent on the hot plate. The compounds 4b, 4c, and 4h had increased the latency time compared to the blank solvent group. They have potential application in developing new drug candidates with antinociceptive activity.

Propargyl-trifluoromethoxy-amino-benzothiazole derivatives

The subject invention provides compounds having the structure: wherein R1 is present or absent, and when present is H, C1-C6 alkyl, C1-C6 alkynyl, —(CH2)yS(CH2)x

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.

Versatile methods for the synthesis of 2-amino-6-trifluoromethoxy-(nitro)benzothiazoles

Convenient and regioselective syntheses of all three isomers of mononitro-6-trifluoromethoxy-benzothiazoles, starting from 2-amino-6-trifluoromethoxybenzothiazole (riluzole) are described.

2-alkyliminobenzothiazoline derivatives, processes for preparing them and medicinal products containing them

Compounds of formula: STR1 R1 represents a polyfluoroalkoxy radical, R2 represents an alkylthioalkyl, alkylsulphinylalkyl or alkylsulphonylalkyl radical, and R3 represents an alkyl radical, as well as the salts of these compounds with an inorganic or organic acid, processes for preparing them and medicinal products containing them.