72505-20-5

Usage

Uses

Used in Pharmaceutical Research:
3-Fluorothiobenzamide is used as a research compound for its potential in the development of new drugs. It is valued for its unique structural features, which may contribute to novel pharmacological activities and therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Fluorothiobenzamide is used as a key intermediate or building block. Its presence of fluorine and sulfur atoms allows for the creation of a variety of bioactive molecules and pharmaceutical compounds, enhancing the diversity of chemical libraries for drug discovery.
Used in Drug Development:
3-Fluorothiobenzamide is being studied for its potential role in drug development. Its unique chemical properties may lead to the discovery of new therapeutic agents, particularly in areas where existing treatments are limited or ineffective.
While the specific applications and uses of 3-fluorothiobenzamide are still under investigation, its presence in the pharmaceutical and chemical research fields highlights its potential as a versatile and valuable compound for future scientific advancements.

InChI:InChI=1/C7H6FNS/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H2,9,10)

Upstream product

• 403-54-3 m-Fluorobenzonitrile 
• 455-37-8 3-fluorobenzamide 

Downstream Products

• 54872-79-6 3-fluoro-N'-hydroxybenzenecarboximidamide 
• 250258-58-3 2-(2-(2-(3-fluorophenyl)thiazol-4-yl)ethyl)isoindoline-1,3-dione 
• 27423-83-2 2-(3-fluorophenyl)-4,5-dihydro-1H-imidazole 
• 1309457-33-7 5-(3-Fluorophenyl)-3H-1,2,4-dithiazol-3-thione 
• 1314082-92-2 3-[2-(3-fluorophenyl)-1,3-thiazol-4-yl]-1-methyl-1H-7-azaindole 
• 1314082-90-0 3-[2-(3-fluorophenyl)-1,3-thiazol-4-yl]-1H-7-azaindole 
• 1428254-80-1 3-[2-(3-fluorophenyl)-1,3-thiazol-4-yl]-1H-isochromen-1-one 
• 953736-97-5 4-chloromethyl-2-(3-fluoro-phenyl)-thiazole 
• 1589081-09-3 4-amino-6-(benzo[d][1,3]dioxol-5-yl)-2-((2-(3-fluorophenyl)thiazol-4-yl)methylthio)pyrimidine-5-carbonitrile 
• 1262444-19-8 4-(2-(3-fluorophenyl)thiazol-4-yl)benzenamine 
• 1649449-22-8 3-(4-(2-(3-fluorophenyl)thiazol-4-yl)phenyl)-2-(4-methyl-2-phenylthiazol-5-yl)thiazolidin-4-one 
• 1649449-13-7 4-(2-(3-fluorophenyl)thiazol-4-yl)-N-((4-methyl-2-phenylthiazol-5-yl)methylene)benzenamine 
• 948292-06-6 ethyl 2-(3-fluorophenyl)-4-methylthiazole-5-carboxylate 

Relevant academic research and scientific papers

Structural and Activity Relationships of 6-Sulfonyl-8-Nitrobenzothiazinones as Antitubercular Agents

The benzothiazinone (BTZ) scaffold compound PBTZ169 kills Mycobacterium tuberculosis by inhibiting the essential flavoenzyme DprE1, consequently blocking the synthesis of the cell wall component arabinans. While extraordinarily potent against M. tuberculosis with a minimum inhibitory concentration (MIC) less than 0.2 ng/mL, its low aqueous solubility and bioavailability issues need to be addressed. Here, we designed and synthesized a series of 6-methanesulfonyl substituted BTZ analogues; further exploration introduced five-member aromatic heterocycles as linkers to attach an aryl group as the side chain. Our work led to the discovery of a number of BTZ derived compounds with potent antitubercular activity. The optimized compounds 6 and 38 exhibited MIC 47 and 30 nM, respectively. Compared to PBTZ169, both compounds displayed increased aqueous solubility and higher stability in human liver microsomes. This study suggested that an alternative side-chain modification strategy could be implemented to improve the druglike properties of the BTZ-based compounds.

Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions

Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.

Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C-H activation

A regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium catalysis was developed. This transformation tactically linked the 1,2,4-thiadiazoles and succinimides together, and the novel molecules formed may have potential biological activity.

A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature

A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.

A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles

A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.

4-HYDROXY-2-PHENYL-1,3-THIAZOL-5-YL METHANONE DERIVATIVES AS TRPM8 ANTAGONISTS

The invention relates to compounds acting as antagonists of Transient Receptor Potential cation channel subfamily M member 8 (TRPM8), and having formula (I): Said compounds are useful in the treatment of diseases associated with activity of TRPM8 such as pain, ischaemia, neurodegeneration, stroke, psychiatric disorders, itch, irritable bowel diseases, cold-induced and/or exacerbated- respiratory disorders, urological disorders, corneal disordes associated to disturbances in the production of the tears and/or altered blinking such as epiphora and dry eye disease.

Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.

Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new oxadiazole and thiazole analogs

A series of 2-adamantyl-5-arylthiazolyl-1,3,4-oxadiazoles 7a–x together with thiazoles 13 and 14 were synthesized. Compounds 7a–l, 13, and 14 were tested in vitro with the aim of identifying novel lead compounds active against human immunodeficiency virus type-1 and human immunodeficiency virus type-2 activity in MT-4 cells. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various mycobacterial strains (Mycobacterium fortuitum and Mycobacterium smegmatis), yeast (Candida albicans), and mold (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity, except compounds 13 and 14 exhibited anti-human immunodeficiency virus-1 activity with EC50 values of 1.79 and 2.39 μM with Selectivity index = 18 and 4, respectively. On the other hand, compounds 7a and 7j showed a marked cytotoxicity against the human CD4+ lymphocytes (MT-4). Therefore, 7a and 7j were evaluated for their antiproliferative activity against two solid tumor-derived cell lines, which exhibited IC50 values of 8.1 ± 0.10 μM and 4.8 ± 0.08 μM against Hep-G2 cell lines, respectively.

2-ARYL-4-HYDROXY-1,3-THIAZOLE DERIVATIVES USEFUL AS TRPM8-INHIBITORS IN TREATMENT OF NEURALGIA, PAIN, COPD AND ASTHMA

The invention relates to compounds acting as selective antagonists of Transient Receptor Potential cation channel subfamily M member 8 (TRP.M8), and having formula (I). Said compounds are useful in the treatment of diseases associated with activity of TRPM8 such as pain, inflammation, ischaemia, neurodegeneration, stroke, psychiatric disorders, itch, irritable bowel diseases, cold induced and/or exacerbated respiratory disorders and urological disorders.

Crystal landscape of primary aromatic thioamides

The crystal landscape of a series of primary aromatic thioamides is described, displaying similar characteristic intermolecular hydrogen-bonding interactions in the solid state to those observed in their widely studied amide analogues, including R22(8) dimers and C(4) chains. In a number of cases, high Z′ values were observed in the structures. On the basis of the observed solid-state features, the thioamide functional group, which is a strong hydrogen-bond donor and moderate acceptor, offers considerable potential as a key moiety for crystal engineering.