3335-44-2

Usage

Uses

Used in Pharmaceutical Development:
2-OXO-6-PHENYL-4-(TRIFLUOROMETHYL)-1,2-DIHYDRO-3-PYRIDINECARBONITRILE is used as a lead compound for the development of new pharmaceuticals due to its potential to modulate enzyme activity or protein function. Its unique structural features make it a promising candidate for targeting specific biological pathways implicated in various diseases.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-OXO-6-PHENYL-4-(TRIFLUOROMETHYL)-1,2-DIHYDRO-3-PYRIDINECARBONITRILE serves as a valuable tool for studying the interactions between small molecules and biological targets. Its properties can be further optimized to enhance its efficacy and selectivity in modulating the desired biological processes.
Used in Drug Discovery:
2-OXO-6-PHENYL-4-(TRIFLUOROMETHYL)-1,2-DIHYDRO-3-PYRIDINECARBONITRILE is utilized in drug discovery efforts as a starting point for the design of novel therapeutic agents. Its chemical structure can be modified to create a series of analogs with improved pharmacological properties, such as increased potency, selectivity, and reduced side effects.
Used in Biochemical Studies:
In biochemical research, 2-OXO-6-PHENYL-4-(TRIFLUOROMETHYL)-1,2-DIHYDRO-3-PYRIDINECARBONITRILE is employed to investigate the mechanisms of enzyme inhibition or activation. Understanding its interactions with specific proteins can provide insights into the development of targeted therapies for various diseases.
Used in Drug Design and Optimization:
2-OXO-6-PHENYL-4-(TRIFLUOROMETHYL)-1,2-DIHYDRO-3-PYRIDINECARBONITRILE is used as a template in drug design and optimization processes. Its structure can be systematically modified to generate a series of compounds with improved pharmacokinetic and pharmacodynamic profiles, leading to the development of more effective and safer drugs.

InChI:InChI=1/C13H7F3N2O/c14-13(15,16)10-6-11(8-4-2-1-3-5-8)18-12(19)9(10)7-17/h1-6H,(H,18,19)

Upstream product

• 104960-52-3 2,2-bis-(4-trifluoromethyl-6-phenyl-3-cyano-2-pyridyl) disulfide 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 109-77-3 malononitrile 
• 155635-57-7 2-((3-cyano-6-phenyl-4-(trifluoromethyl)pyridin-2-yl)oxy)acetamide 
• 104960-49-8 2-thioxo-6-phenyl-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile 
• 82959-36-2 1-benzoyl-2-(1-morpholino)-3,3,3-trifluoro-1-propene 
• 107-91-5 cyanoacetic acid amide 
• 98-86-2 acetophenone 

Downstream Products

• 114084-91-2 4-trifluoromethyl-6-phenyl-2-chloro-3-cyanopyridine 
• 155635-57-7 2-((3-cyano-6-phenyl-4-(trifluoromethyl)pyridin-2-yl)oxy)acetamide 
• 155635-64-6 ethyl 2-((3-cyano-6-(phenyl)-4-(trifluoromethyl)pyridin-2-yl)oxy)acetate 
• 160436-52-2 2-carbohydrazide-3-amino-4-trifluoromethyl-6-phenylfuro-<2,3-b>-pyridine 
• 160436-48-6 2-carbethoxy-3-amino-4-trifluoromethyl-6-phenylfuro-<2,3-b>-pyridine 
• 104960-49-8 2-thioxo-6-phenyl-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile 
• 114084-96-7 2-(N,N-dimethylamino)-4-trifluoromethyl-6-phenyl-3-cyanopyridine 
• 114084-92-3 2-ethylamino-6-phenyl-4-trifluoromethylnicotinonitrile 
• 114085-01-7 2-azido-4-trifluoromethyl-6-phenyl-3-cyanopyridine 
• 114084-97-8 2-Diethylamino-6-phenyl-4-trifluoromethyl-nicotinonitrile 
• 114084-95-6 2-(2-Hydroxy-ethylamino)-6-phenyl-4-trifluoromethyl-nicotinonitrile 

Relevant academic research and scientific papers

Simple and highly efficient method for the deprotection of allyl ethers using dimethylsulfoxide-sodium iodide

A simple and highly efficient method for deprotection of allyl ethers has been developed using dimethylsulfoxide-sodium iodide (catalytic amount). This method is inexpensive, has simple reaction conditions, has an easy workup procedure, proceduces excellent yields (60-99%), and is effective for several structurally varied allyl ethers. Copyright Taylor & Francis Group, LLC.

Design, synthesis and structure-activity evaluation of novel 2-pyridone-based inhibitors of α-synuclein aggregation with potentially improved BBB permeability

The treatment of Parkinson's disease (PD), the second most common neurodegenerative human disorder, continues to be symptomatic. Development of drugs able to stop or at least slowdown PD progression would benefit several million people worldwide. SynuClea

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 and adenosine receptors binding studies of new fluorinated analogues of pyrido[2,3-d]pyrimidines and quinazolines

A series of new fluorine containing pyrido[2,3-d]pyrimidines and imidazo[1,2-c]pyrido[3,2-e]pyrimidines along with a series of bioisosteric fluorinated quinazolines were synthesised following appropriate synthetic schemes and characterised by spectral analytical means. X-ray crystal structure of the key precursor 1 (2-amino-3-cyano-4-trifluoro-methyl-6-phenyl-pyridine) was also determined to gain insight into its reactivity. Binding affinity data of all the compounds for adenosine receptors (ARs) showed that pyrido[2,3-d]pyrimidine scaffold with free amino (NH2) group at 2- and 4-position (2a) exhibited the maximum binding affinity for hA3 AR with similar affinity for the hA1 and somewhat lower affinity for hA2A ARs resulting in a compound with no A3 selectivity vs. A1 and moderate selectivity vs. A2A AR (Ki hA1 = 0.62 μM, hA2A = 3.59 μM and hA3 = 0.42 μM). Interestingly, the replacement of both the amino groups with carbonyl (C=O) groups (compound 4) resulted in significantly improved affinity for hA1 AR but with moderate selectivity against hA2A and hA3 ARs (Ki hA1 = 0.17 μM, hA2A = 0.67 μM and hA3 =0.68 μM). In case of fluorinated quinazolines, only compound 18a showed remarkable affinity for hA1 AR with significant selectivity against hA2A and hA3 ARs (Ki hA1 = 0.73 μM, hA2A CloseSPigtSPi 30 μM and hA3 = 9.27 μM). The preliminary results of these compounds demonstrate that the fluorinated pyrido[2,3-d]pyrimidine and imidazo[1,2-c]pyrido[3,2-e]pyrimidine can be considered as promising scaffolds for further optimisation in search of potential antagonists with better affinity and selectivity towards hA1 and hA3 ARs.

Design, synthesis and biological evaluation of benzimidazole-pyridine-piperidine hybrids as a new class of potent antimicrobial agents

A series of novel benzimidazole-pyridine-piperidine hybrids was synthesized in good yields and characterized by spectral and elemental analyses. The compounds 4a-h and 5a-c were evaluated for their in vitro antibacterial activity against gram-positive org

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, characterization and antitumor activity of novel triazole/isoxazole tagged pyridine hybrids

A series of novel 2-((1-substituted-1H-1,2,3-triazol-4-yl/3- substitutedisoxazol-5-yl)methoxy) substituted pyridine, 1-((1-substituted-1H-1, 2,3-triazol-4-yl/3-substitutedisoxazol-5-yl)methyl)substituted pyridin-2(1H)-one was prepared from 2-oxo-6-phenyl/methyl-4-(trifluoromethyl)-1,2- dihydropyridine-3-carbonitrile 3 via propargylation followed by 1,3-dipolar cycloaddition of the propargyl derivatives 4 and 5. These triazole/isoxazole tagged pyridine derivatives were evaluated for antitumor activity against breast cancer cell lines such as MDA-MB-231, MCF-7 etc. The results indicated that compounds 6e, 6f, 8e and 8f were found to be active on MDA-MB-231, while 6h and 8h were active on MCF-7.

Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines

A series of novel 8/10-trifluoromethyl-substituted-imidazo[1,2-c] quinazolines have been synthesized and evaluated in vivo (rat paw edema) for their anti-inflammatory activity and in silico (docking studies) to recognize the hypothetical binding motif of the title compounds with the cyclooxygenase isoenzymes (COX-1 and COX-2) employing GOLD (CCDC, 4.0.1 version) software. The compounds, 9b and 10b, were found to have good anti-inflammatory activity [around 80% of the standard: indomethacin]. The binding mode of the title compounds has been proposed based on the docking studies.

A simple and facile method for the synthesis of novel 5/7 triflouromethyl-substituted 4(3H)-quinazolone regioisomers

The unsymmetrical 1,3-diketones 1 on reaction with malononitrile is resulted an interesting trifunctional intermediates 2 and 3. The intermediate 2 is hydrolyzed to give 2,6-dicarboxamido aniline 4 which on cyclisation gave two regioisomers of 1,2-dihydro-4(3H)-quinazolinones 5 and 6. The effect of substituents on compound 4 is characteristic for formation of regioisomers in different proportions. Each regioisomer on dehydrogenation under mild condition using active MnO2 gave corresponding 4(3H)-quinazolones 7 and 8, respectively.