75356-07-9

Basic information

• Product Name: 3-Pyridinecarbonitrile, 2-amino-6-(4-chlorophenyl)-4-phenyl-
• Synonyms: 3-Pyridinecarbonitrile, 2-amino-6-(4-chlorophenyl)-4-phenyl-
• CAS NO: 75356-07-9
• Molecular Formula: C₁₈H₁₂ClN₃
• Molecular Weight: 305.76098
• Mol File: 75356-07-9.mol
• Article Data: 27

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Pyridinecarbonitrile, 2-amino-6-(4-chlorophenyl)-4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarbonitrile, 2-amino-6-(4-chlorophenyl)-4-phenyl-(75356-07-9)
• EPA Substance Registry System: 3-Pyridinecarbonitrile, 2-amino-6-(4-chlorophenyl)-4-phenyl-(75356-07-9)

Safety Data

• Hazardous Substances Data: 75356-07-9(Hazardous Substances Data)

Upstream product

• 1956-39-4 4-chloroacetophenone oxime 
• 100-52-7 benzaldehyde 
• 109-77-3 malononitrile 
• 99-91-2 para-chloroacetophenone 
• 956-04-7 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one 
• 956-02-5 4'-chlorochalcone 
• 111039-37-3 2-Amino-6-(4-chloro-phenyl)-1-oxy-4-phenyl-nicotinonitrile 

Downstream Products

• 138744-57-7 7-(4-chlorophenyl)-5-phenylpyrido[2,3-d]pyrimidin-4-amine 
• 145208-72-6 4-Amino-7-(4-chloro-phenyl)-5-phenyl-1H-pyrido[2,3-d]pyrimidin-2-one 
• 1370255-91-6 1-[6-(4-chlorophenyl)-3-cyano-4-phenylpyridin-2-yl]-5-oxopyrrolidine-3-carboxylic acid 
• 138744-68-0 7-(4-chlorophenyl)-2-methyl-5-phenyl-3,4-dihydropyrido[2,3-d]pyrimidin-4-one 
• 1392014-19-5 2-(4-bromophenylamino)-6-(4-chlorophenyl)-4-phenylnicotinonitrile 
• 1392014-11-7 6-(4-chlorophenyl)-4-phenyl-2-(p-tolylamino)nicotinonitrile 
• 1392014-10-6 6-(4-chlorophenyl)-4-phenyl-2-(phenylamino)nicotinonitrile 
• 138744-65-7 7-(4-Chloro-phenyl)-5-phenyl-2-piperidin-1-ylmethyl-3H-pyrido[2,3-d]pyrimidin-4-one 
• 138744-62-4 2-Chloromethyl-7-(4-chloro-phenyl)-5-phenyl-3H-pyrido[2,3-d]pyrimidin-4-one 
• 281225-33-0 7-(4-chloro-phenyl)-3-(2-methoxy-phenyl)-5-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-d]pyrimidin-4-one 
• 281225-34-1 7-(4-chloro-phenyl)-3-(4-methoxy-phenyl)-5-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-d]pyrimidin-4-one 
• 138744-59-9 2-Chloro-N-[6-(4-chloro-phenyl)-3-cyano-4-phenyl-pyridin-2-yl]-acetamide 
• 145208-70-4 4-Amino-7-(4-chloro-phenyl)-5-phenyl-1H-pyrido[2,3-d]pyrimidine-2-thione 
• 138744-50-0 2-(4-Chloro-phenyl)-4-phenyl-6,7,8,9-tetrahydro-benzo[b][1,8]naphthyridin-5-ylamine 

Relevant articles and documents

One-Pot Expeditious Synthesis of 2-Amino-4,6-(disubstituted)nicotinonitriles Using Activated Fuller’s Earth as Catalyst

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Amberlyst-15 catalysed sonochemical synthesis of 2-amino-4,6-disubstituted nicotinonitrile derivatives and their biological evaluation

The 2-amino nicotinonitrile framework has been explored first time for the identification of potential inhibitors of SIRT1. Thus a series of targeted 2-amino-4,6-disubstituted nicotinonitrile derivatives were synthesized by employing an ultrasound assisted MCR of ketones, aldehydes, malononitrile and ammonium acetate. The MCR was carried out in the presence of Amberlyst-15 in MeCN under mild conditions to give the desired product in good yields. The reaction was less efficient in the absence of air whereas combination of Amberlyst-15, ultrasound, air and MeCN was essential for the success of this MCR. Several of the synthesized compounds showed good activities when tested for their SIRT1 inhibitory potential in vitro among which 5c, 5e and 5n were identified as the most potent (IC50 ~ 3 μM) and were better than the known inhibitor nicotinamide (IC50 ~109 μM). In the in silico docking studies these three compounds showed better binding energy (> 100 kcal/mol) and higher number of interactions than nicotinamide (binding energy -88.38 kcal/mol). While both amino (–NH2) and cyano (–CN) groups of nicotinonitrile derivatives formed H-bonds with the ASN346 and HIS363 residue respectively the nicotinamide showed similar interactions with ASP348 and ILE347 through its amide (–CONH2) moiety. Compound 5c, 5e and 5n has been identified as initial hits for further study.

Synthesis of a novel acidic ionic liquid catalyst and its application for preparation of pyridines via a cooperative vinylogous anomeric-based oxidation

Abstract: In the current study, a novel acidic ionic liquid catalyst based on 8-hydroxyquinoline, namely 8,8′,8″-([1,3,5-triazine-2,4,6-triyl]tris[oxy])tris(1-sulfoquinolin-1-ium)chloride (TTS), was designed and synthesized. The structure of the prepared acidic ionic liquid (AIL) was fully investigated by using Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray (EDX) analysis, thermogravimetric analysis/differential thermal analysis (TGA/DTA), 1HNMR, 13CNMR and mass spectroscopy. Then, the catalytic performance of described AIL was successfully inspected toward the four-component synthesis of pyridine derivatives via a cooperative vinylogous anomeric-based oxidation. Graphic abstract: Novel AIL (TTS) showed a very high efficiency in the synthesis of pyridines. [Figure not available: see fulltext.].