78364-55-3

Usage

Uses

As the specific applications of 6-Fluoro-2(3H)-benzothiazolone hydrazone are not well-documented, the following uses are inferred based on its role in scientific research:
Used in Chemical Research:
6-Fluoro-2(3H)-benzothiazolone hydrazone is used as a research compound for exploring its chemical properties and potential interactions with other substances. Its unique molecular structure may offer insights into new chemical reactions or mechanisms, contributing to the advancement of chemical science.
Used in Material Science:
In the field of material science, 6-Fluoro-2(3H)-benzothiazolone hydrazone may be employed as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials could potentially enhance their characteristics, such as stability, reactivity, or selectivity.
Used in Pharmaceutical Development:
Given the compound's presence in scientific research, 6-Fluoro-2(3H)-benzothiazolone hydrazone could be utilized in the pharmaceutical industry for drug discovery and development. Its unique structure may provide a basis for designing new drug candidates with potential therapeutic applications.
Used in Environmental Applications:
6-Fluoro-2(3H)-benzothiazolone hydrazone may also find use in environmental science, where it could be studied for its potential role in environmental remediation or pollution control. Its chemical properties might enable it to interact with pollutants or contaminants, facilitating their removal or degradation.

Upstream product

• 348-40-3 2-amino-6-fluoro-1,3-benzothiazole 
• 371-40-4 4-fluoroaniline 
• 399-74-6 2-chloro-6-fluorobenzothiazole 
• 459-05-2 (4-fluoro-phenyl)-thiourea 

Downstream Products

• 92537-77-4 6-Fluoro-2-(3'-methyl-5'-oxo-2'-pyrazolin-1'-yl)benzothiazole 
• 106515-45-1 1-(6-Fluoro-benzothiazol-2-yl)-3,4-dimethyl-1H-pyrano[2,3-c]pyrazol-6-one 
• 92537-80-9 4-Chloro-2-(6-fluoro-benzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ol 
• 399-74-6 2-chloro-6-fluorobenzothiazole 
• 1033804-50-0 1-(6-fluorobenzothiazol-2-yl)-3-(4-fluorophenyl)-5-phenylpyrazoline 
• 1033804-52-2 C₂₂H₁₄ClF₂N₃S 
• 1033804-51-1 C₂₂H₁₄F₃N₃S 
• 1033804-54-4 C₂₃H₁₇F₂N₃OS 
• 1111097-33-6 C₁₄H₁₀ClFN₄S₂ 
• 1111097-27-8 C₁₄H₁₀F₂N₄S₂ 
• 1111097-30-3 C₁₄H₁₀BrFN₄S₂ 
• 1246493-39-9 3-(3-pyridyl)-5-(4-methylphenyl)-4-(N-(6-fluoro-1,3-benzothiazol-2-yl)amino)-4H-1,2,4-triazole 
• 1316270-34-4 C₂₀H₁₂FN₇O₂S 
• 1384952-53-7 1-(6-fluorobenzothiazol-2-yl)-6-methyl-3-(4-methylphenyl)-4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridine 

Relevant academic research and scientific papers

Synthesis, in vitro antitumor activity and molecular modeling studies of a new series of benzothiazole Schiff bases

A new series of benzothiazole Schiff bases 3-29 was synthesized and screened for antitumor activity against cervical cancer (Hela) and kidney fibroblast cancer (COS-7) cell lines. Results indicated that compounds 3, 14, 19, 27 and 28 have promising activity against Hela cell line with IC50 values of 2.41, 3.06, 6.46, 2.22 and 6.25 μmol/L, respectively, in comparison to doxorubicin as a reference antitumor agent (IC50 2.05 μmol/L). In addition, compound 3 displayed excellent activity against COS-7 cell line with IC50 value of 4.31 μmol/L in comparison to doxorubicin (IC50 3.04 μmol/L). In the present work, structure based pharmacophore mapping, molecular docking, protein-ligand interaction, fingerprints and binding energy calculations were employed in a virtual screening strategy to identify the interaction between the compounds and the active site of the putative target, EGFR tyrosine kinase. Molecular properties, toxicity, drug-likeness, and drug score profiles of compounds 3, 14, 19, 27, 28 and 29 were also assessed.

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 of 2-anilinopyridyl linked benzothiazole hydrazones as apoptosis inducing cytotoxic agents

A series of 2-anilinopyridyl linked benzothiazole-hydrazone conjugates (5a-aa) were designed, synthesized and evaluated for their in vitro cytotoxic potency against a panel of cancer cell lines like mouse skin melanoma (B16F10), lung adenocarcinoma (A549), breast adenocarcinoma (MCF-7), triple negative breast cancer (MDA-MB-231) and normal lung epithelial (L132) cell lines. Preliminary screening results revealed that some of these conjugates like 5i and 5l exhibited a significant antiproliferative effect against human breast cancer (MCF-7) with IC50 values of 1.03 and 1.69 μM respectively. Further, detailed biological studies of this promising conjugate (5i) were carried out on MCF-7 cells. The flow cytometric analysis revealed that this conjugate induces cell-cycle arrest in the G2/M phase in a dose dependent manner. Furthermore, in order to determine the effect of the conjugate on cell viability, various cell based assays such as clonogenic assay, ethidium bromide staining, Hoechst staining, detection of ROS generation and annexin V-FITC/PI assays were performed. In these studies, apoptotic features were clearly observed indicating that this conjugate inhibited cell proliferation by apoptosis.

Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists

Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ-induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a-h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR-γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side-effects.

Synthesis of novel 7-fluoro-3-substituted-1,2,4-triazolo[3,4-b]benzothiazoles (FTBs) as potent antifungal agents: molecular docking and in silico evaluation

A novel series of fluorinated 1,2,4-triazolo[3,4-b]benzothiazoles was synthesized by fusion of proven antifungal lead 1,2,4-triazole with flourinated benzothiazole nucleus exploiting lead hybridization strategy. Their in vitro antifungal assay against various phytopathogenic fungi revealed that a 2- or 3-chlorinated aryl group at the 3-position of the fused system yielded outstanding and remarkable results of fungitoxicity. Compounds 3b and 3c were found to inflict the best fungitoxicity against most of the test fungi (EC50 value as low as 0.24 mmoles/L) with results better than or comparable to standards. In silico molecular docking and Lipinskii indices were in agreement with the observed trend of antifungal activity. Moreover, the toxicity analysis showed that the compounds belong to class III of toxicity which is the same as that of the recommended standards used.

Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of benzothiazole derivatives

New series of benzothiazole derivatives were designed and synthesized. The newly synthesized compounds were screened for their antibacterial activity against Escherichia coli, Staphylococcus aureus and Bacillus cereus. Compounds 6j and 6o showed the highest activity against E. coli and S. aureus. The antifungal activity of these compounds was also tested against Candida albicans and Aspergillus fumigatus 293. Compounds 4c, 4g and 6j exhibited the highest activity against C. albicans. In addition, compounds 4a and 6j displayed promising activity against A. fumigatus 293. The same compounds were examined for their antiquorum-sensing activity against Chromobacterium violaceum ATCC 12472, whereas compounds 4a, 6j and 6p showed moderate activity. The in vitro cytotoxicity testing of the synthesized compounds was performed against cervical cancer (Hela) and kidney fibroblast cancer (COS-7) cell lines. Results indicated that all tested compounds have IC50 values >50 μmol/L against both cell lines. Molecular properties, toxicities, drug-likeness, and drug score profiles of compounds 4a-c, 5a, 6g,h, 6j, 6l, 6o and 7c,d were also assessed.

A facile and efficient synthesis of 2-(5-(4-substitutedphenyl)-4, 5-dihydro-3-phenylpyrazol-1-yl)-6-substitutedbenzothiazoles and their biological studies

A series of new 1-substituted 3, 5-diarylpyrazolines (10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25) were synthesized in good yield by both conventional and microwave-assisted synthesis from α, β- unsaturated ketones (6, 7, 8, 9) in n-butanol and benzothiazole hydrazines (2, 3, 4, 5). All the new compounds were characterized by IR, NMR, and mass spectral data. The synthesized compounds (10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25) were evaluated for antibacterial and anthelmintic activities. The compounds showed potent anthelmintic activity against earthworm species (Eudrilus eugeniae) and moderate antibacterial activity against bacterial strains such as Gram positive bacteria, Enterococcus faecalis, Staphylococcus aureus, and Bacillus subtilis, and Gram negative bacteria, Escherichia coli and Proteus mirabilis.

Discovery of potent and selective benzothiazole hydrazone inhibitors of Bcl-XL

Developing potent molecules that inhibit Bcl-2 family mediated apoptosis affords opportunities to treat cancers via reactivation of the cell death machinery. We describe the hit-to-lead development of selective Bcl-X L inhibitors originating from a high-throughput screening campaign. Small structural changes to the hit compound increased binding affinity more than 300-fold (to IC50 w L. Surface plasmon resonance experiments afford strong evidence of binding affinity within the hydrophobic groove of Bcl-XL. Biological experiments using engineered Mcl-1 deficient mouse embryonic fibroblasts (MEFs, reliant only on Bcl-XL for survival) and Bax/Bak deficient MEFs (insensitive to selective activation of Bcl-2-driven apoptosis) support a mechanism-based induction of apoptosis. This manuscript describes the first series of selective small-molecule inhibitors of Bcl-XL and provides promising leads for the development of efficacious therapeutics against solid tumors and chemoresistant cancer cell lines.

Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives

In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics.