3335-45-3

Usage

Uses

Used in Organic Chemistry:
2-HYDROXY-6-(2-THIENYL)-4-(TRIFLUOROMETHYL)NICOTINONITRILE is used as a precursor for the synthesis of complex molecules, particularly in the field of organic chemistry. Its unique structure, which includes a thiophene ring and trifluoromethyl groups, makes it a valuable building block for the development of new compounds.
Used in Medicinal Chemistry:
2-HYDROXY-6-(2-THIENYL)-4-(TRIFLUOROMETHYL)NICOTINONITRILE is used as a starting material for the design and synthesis of new pharmaceutical compounds. Its potential as a precursor for drug development is due to the presence of nitrogenous bases and the ability to form various molecular structures that could exhibit therapeutic properties.
Used in Industrial Applications:
2-HYDROXY-6-(2-THIENYL)-4-(TRIFLUOROMETHYL)NICOTINONITRILE is used as a chemical intermediate in the production of various industrial products. Its versatility in forming different molecular structures allows it to be a key component in the synthesis of materials with specific properties, such as dyes, pigments, and specialty chemicals.

Upstream product

• 326-91-0 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione 
• 107-91-5 cyanoacetic acid amide 
• 2700-22-3 Benzylidenemalononitrile 
• 88-15-3 2-Acetylthiophene 

Downstream Products

• 22123-11-1 6-thiophen-2-yl-4-(trifluoromethyl)pyridine-2(1H)-one 
• 924990-23-8 C₁₃H₇F₃N₂O₃S 
• 1581726-07-9 ethyl 3-amino-6-(thiophen-2-yl)-4-(trifluoromethyl) furo [2,3-b]pyridine-2-carboxylate 

Relevant academic research and scientific papers

Synthesis and antimicrobial activity of 4-trifluoromethylpyridine nucleosides

4-Trifluoromethylpyridine derivatives 4-8 represent good candidates for the discovery of new antibacterial agents. Fluorinated pyridine nucleosides 4-7 and non-nucleoside analogues 8a,b were synthesized and evaluated for their antibacterial activities aga

Green Synthetic Approach and Antimicrobial Evaluation for Some Novel Pyridyl Benzoate Derivatives

Two series of substituted pyridyl 4-chlorobenzoates have been synthesized by microwave-assisted condensation of the corresponding 2-oxo-1,2-dihydropyridine-3-carbonitriles with 4-chlorobenzoyl chloride under solvent-free conditions. Alternatively, some compounds have also been prepared by conventional heating in methylene chloride in the presence of triethylamine. The structure of the synthesized compounds has been confirmed by spectral data (FTIR, 1D and 2D NMR). The new pyridyl benzoates were evaluated for antibacterial activity against gram-negative and gram-positive bacteria. The activity of 3-cyano-5-[(4-hydroxyphenyl)diazenyl]-4-methyl-6-phenylpyridin-2-yl 4-chlorobenzoate against gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) was comparable to that of amikacin used as standard antibiotic.

Synthesis of novel hetero ring fused pyridine derivatives; Their anticancer activity, CoMFA and CoMSIA studies

A series of novel furo[2,3-b]pyridine-2-carboxamide 4a–h/pyrido[3′,2′:4,5]furo[3,2-d] pyrimidin-4(3H)-one derivatives 5a–p were prepared from pyridin 2(1H) one 1 via selective O-alkylation with α-bromoethylester followed by cyclization, then reaction with

Synthesis of novel triazolothione, thiadiazole, triazole-functionalized furo/thieno[2,3-b]pyridine derivatives and their antimicrobial activity

A series of novel triazolothione, thiadiazole, triazole-functionalized furo/thieno[2,3-b]pyridine derivatives 9a–l, respectively, were prepared starting from 2 (1H) pyridone 3 through selective O/S-alkylation followed by Thorpe–Ziegler cyclization to form furo/thieno[2,3-b]pyridine derivatives 6. Compounds 6 on reaction with hydrazine hydrate resulted carbohydrazide derivatives 7 and further reacted with diverse substituted phenyl isothiocyanates to form phenyl hydrazine carbothiamide derivatives 8. Each compound 8 is independently reacted in presence of NaOH, H2SO4, and N2H4.H2O to form triazolothione, thiadiazole, triazole-functionalized furo/thieno[2,3-b]pyridine derivatives 9a–l, respectively. All the products 9a–l were screened against Gram +ve, Gram –ve bacteria and fungal strains. Compounds 9c–h showed high activity against Bacillus subtilis microbial-type culture collection (MTCC) 121 at 8.0 micromolar concentration. Promising compounds further screened for minimum bactericidal concentration against B. subtilis MTCC 121 using ciprofloxacin as standard and found to show very good activity. These compounds also screened for biofilm inhibition activity against B. subtilis MTCC 121 using erythromycin as standard and confirmed the high activity.

Discovery and structure-activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors

Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[2,3-b]pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 μM, SI >30.3, 12b, EC50 = 3.5 μM, SI >28.6, 10l, EC50 = 3.9 μM, SI >25.6, 12o, EC 50 = 4.5 μM, SI >22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents.

Synthesis and reactions of 4-trifluoromethyl-3-cyano pyridine-2(1H)-thione/ one derivatives

4,4,4-Trifluoro-1-(thiophen-2-yl)butane-1,3-dione was reacted by grinding with cyanothioacetamide and cyanoacetamide under solvent-free conditions at 25°C to give pyridine-2(1H)thione/one derivatives in excellent yields. These compounds were further reacted by grinding with different halogenated reagents to give 2-S/O-alkyl pyridine derivatives. The latter compounds were utilized for the synthesis of thieno[2,3-b]pyridine, pyrazolopyridine, pyridothienopyrimidine and pyridothienooxazinone derivatives.

Preparative synthesis of 3-cyano-4-difluoromethyl-and 3-cyano-4-trifluoromethyl-2(1H)-pyridones

An efficient procedure for the synthesis of 3-cyano-4-difluoromethyl-and 3-cyano-4-trifluoromethyl-2(1H)-pyridones was developed. The structure of one of the resulting compounds was established by X-ray diffraction analysis.

CYCLIZATION REACTIONS OF NITRILES. REACTION OF ARYLIDENEMALONONITRILES WITH 1,3-DICARBONYL COMPOUNDS

The reaction of 1,3-dicarbonyl compounds with arylidene derivatives of malononitrile and ethyl cyanoacetate leads to the formation of substituted 2-amino-4H-pyrans.In the case of 1,1,1-trifluoro-3-(2-thenoyl)acetone acid cleavage of the Michael adduct occurs, and this leads to 2-aryl-3-(2-thenoyl)-1,1-dicyanopropanes. 1,3-Indanedione reacts by exchange of the methylene components and gives the corresponding 2-arylidene-1,3-indanediones.