22179-72-2

Usage

Chemical Properties

Yellow crystaline powder or flakes

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

Upstream product

• 19172-47-5 Lawessons reagent 
• 824-75-9 p-fluorobenzamide 
• 1194-02-1 4-fluorobenzonitrile 
• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 
• 459-23-4 4-fluorobenzaldoxime 
• 459-57-4 4-fluorobenzaldehyde 
• 403-43-0 4-fluorobenzoyl chloride 
• 456-22-4 4-Fluorobenzoic acid 

Downstream Products

• 131786-86-2 2-(4-fluorophenyl)-4-hydroxy-5-phenylthiazole 
• 74466-82-3 N-[1-Dimethylamino-eth-(E)-ylidene]-4-fluoro-thiobenzamide 
• 78742-98-0 ethyl 2-(2-(4-fluorophenyl)thiazol-4-yl)acetate 
• 145916-17-2 (S)-4-[2-(4-Fluoro-phenyl)-thiazol-4-ylmethyl]-2,2-bis-trifluoromethyl-oxazolidin-5-one 
• 85558-98-1 3-(4-Fluoro-phenyl)-[1,4,2]dithiazole-5-thione 
• 159267-53-5 p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(4-fluorophenyl)thiazol-4-yl>-3-cephem-4-carboxylate 
• 150582-60-8 (5S)-5-(2-(4-fluorophenyl)-1,3-thiazol-4-ylmethyl)-2,2-bis-(trifluoromethyl)-1,3-dioxolan-4-one 
• 1026822-84-3 4-[2-(4-fluorophenyl)-thiazol-4-ylmethyl]-2,2-bis(trifluoromethyl)-1,3-oxathiolan-5-one 
• 317319-17-8 4-methyl-2-(4-fluorophenyl)thiazole-5-carboxylic acid ethyl ester 
• 553679-94-0 2,6-di(tert-butyl)-4-((p-fluoro)phenyl)-6H-1,3,5-oxathiazine S-oxide 
• 937079-09-9 1-[2-(4-fluorophenyl)-1,3-thiazol-4-yl]ethanone 
• 444615-63-8 diethyl 2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-4,5-dicarboxylate 
• 1126253-10-8 6-carboxy-2-(4'-fluorophenyl)-1,3-benzothiazole 
• 1182010-84-9 C₁₇H₁₂FNO₂S 

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.

Substituted pyrimidine compound and application thereof

The present invention discloses a substituted pyrimidine compound, which has a structure represented by a general formula I, wherein each substituent is defined in the specification. According to thepresent invention, the compound has a broad-spectrum bactericidal activity, can provide excellent prevention and control effects on cucumber downy mildew, wheat powdery mildew, corn rust disease, riceblast, cucumber anthracnose and the like, and particularly can provide good prevention effects on powdery mildew, corn rust disease and rice blast.

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.

Synthesis of imidazo[1,2-: C] thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides

Building new biological molecules is challenging. Herein, imidazo[1,2-c]thiazoles were synthesized as a new class of heterobicyclic analogs through Pd-catalyzed cascade bicyclization from isonitriles with thioamides. The bicyclic scaffolds were constructed by inserting three molecules of isonitrile into two molecules of thioamide and then cyclizing them in a one-pot procedure. In vitro antitumor studies of these new compounds were conducted by using the MTT assay, and compound 3c showed excellent inhibitory effects against HepG2 at 7.06 ± 0.68 μM.

Optimization, Structure-Activity Relationship, and Mode of Action of Nortopsentin Analogues Containing Thiazole and Oxazole Moieties

Plant diseases seriously endanger plant health, and it is very difficult to control them. A series of nortopsentin analogues were designed, synthesized, and evaluated for their antiviral activities and fungicidal activities. Most of these compounds displayed higher antiviral activities than ribavirin. Compounds 1d, 1e, and 12a, with excellent antiviral activities, emerged as novel antiviral lead compounds, among which 1e was selected for further antiviral mechanism research. The mechanism research results indicated that these compounds may play an antiviral role by aggregating viral particles to prevent their movement in plants. Further fungicidal activity tests revealed that nortopsentin analogues displayed broad-spectrum fungicidal activities. Compounds 2p and 2f displayed higher antifungal activities against Alternaria solani than the commercial fungicides carbendazim and chlorothalonil. Current research has laid a foundation for the application of nortopsentin analogues in plant protection.

Mo (CO)6-assisted Pd-supported magnetic graphene oxide-catalyzed carbonylation-cyclization as an efficient way for the synthesis of 4(3H)-quinazolinones

In this paper, a novel catalyst is introduced based on the immobilization of palladium on modified magnetic graphene oxide nanoparticles. The catalyst is characterized by several methods, including transmission electron microscopy, scanning electron microscopy, X-ray fluorescence, vibrating-sample magnetometer, Fourier transform-infrared and dynamic light scattering (DLS) analysis. The activity of the catalyst was investigated in the synthesis of 4(3H)-quinazolinones via Pd-catalyzed carbonylation-cyclization of N-(2-bromoaryl) benzimidamides by Mo (CO)6. The Mo (CO)6 is used as a carbon monoxide source for performing the reaction under mild conditions. The catalyst showed good reusability, and no change in activity was observed after 10?cycles of recovery.

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.

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.