35982-93-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Pyridinecarbonitrile, 1,2-dihydro-2-oxo-5-phenylis used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Organic Chemistry Research:
In the field of organic chemistry, 3-Pyridinecarbonitrile, 1,2-dihydro-2-oxo-5-phenylis utilized as a versatile building block for the creation of complex organic compounds, facilitating advancements in chemical synthesis and the discovery of novel chemical entities.
Used in Biological and Pharmacological Studies:
3-Pyridinecarbonitrile, 1,2-dihydro-2-oxo-5-phenylis employed in biological and pharmacological research to explore its potential biological activities and pharmacological properties, which may lead to the identification of new therapeutic agents or contribute to a better understanding of molecular mechanisms in biological systems.

InChI:InChI=1/C12H8N2O/c13-7-10-6-11(8-14-12(10)15)9-4-2-1-3-5-9/h1-6,8H,(H,14,15)

Upstream product

• 7089-34-1 ((Z)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate 
• 107-91-5 cyanoacetic acid amide 
• 103-82-2 phenylacetic acid 
• 67382-50-7 3-dimethylamino-2-phenylpropenal 
• 882029-80-3 p-toluenesulfonic acid 3,5-dibromo(pyridin-2-yl) ester 
• 7089-34-1 ((E)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate 

Downstream Products

• 10177-10-3 5-phenyl-2-chloropyridine-3-carbonitrile 
• 10177-08-9 1,2-dihydro-2-oxo-5-phenyl-3-pyridinecarboxylic acid 

Relevant academic research and scientific papers

Reaction mechanism of vinamidinium salts and cyanoacetamide derivatives

The mechanism of formation of a pyridin-2(1H )-one synthesised from vinamidinium salts and cyanoacetamide derivatives is illustrated through the preparation and characterisation of a key intermediate.

Protecting Group-Controlled Regioselective Synthesis for Unsymmetrical 3,5-Disubstituted Pyridones

Protecting group-controlled regioselective functionalization of 3,5-dibromo-2-pyridones has been studied for preparation of unsymmetrical 3,5-disubstituted 2-pyridones. A bulky di-tert-butyl(isobutyl)silyl (BIBS) group was utilized for C5 regioselective arylation in Suzuki-Miyaura reactions. Meanwhile, the p-toluenesulfonyl (Ts) group was used to maximize C3 selective halogen-lithium exchange employing flow chemistry. Most of the reactions proceeded well, with yields of 76 to 95% and excellent regioselectivity. A one-pot synthesis of unsymmetrical 3,5-diaryl-2-pyridones starting from 3,5-dibromo-2-silyloxypyridine was conducted to demonstrate the practical convenience. Further functionalization onto the remaining bromine group, such as transition metal-catalyzed C?C and C?N bond-forming reactions and retro-Brook rearrangement for C?Si bond formation, was accomplished for synthesis of biologically relevant 3,5-disubstituted 2-pyridones. Finally, amrinone and milrinone, commonly used for congestive heart failure, were synthesized in three steps from 3,5-dibromo-2-pyridones in 41% and 56% overall yields, respectively. (Figure presented.).

Design, synthesis and structure-activity relationship studies of morpholino-1H-phenalene derivatives that antagonize Mcl-1/Bcl-2

We report herein characteristic studies of Mcl-1 and Bcl-2 dual inhibitors. It was found that a protruding carbonyl group forming hydrogen bond with R263 plays a predominant role compared with the hydrophobic group that occupies the p2 pocket. A series of dual inhibitors representing different parts of the morpholino-1H-phenalene were designed, synthesized and evaluated.

Fragment-based design, synthesis, and biological evaluation of N-substituted-5-(4-isopropylthiophenol)-2-hydroxynicotinamide derivatives as novel Mcl-1 inhibitors

We have previously reported a nanomolar inhibitor of antiapoptotic Mcl-1 protein, 3-thiomorpholin-8-oxo-8H-acenaphtho [1,2-b] pyrrole-9-carbonitrile (S1). S1 plays its function by binding to the BH3 groove of Mcl-1. Basing on this spacial structural characteristic, we developed a novel class of Mcl-1 inhibitor using fragment-based drug discovery approach. By dissecting S1, we identified the compound 4 with a 2-hydroxypyridine core as the starting fragment. In the following molecular growth, we used the ligand efficiency evaluation and fit quality score to assess the fragments. A novel potent compound, N-benzyl-5-(4-isopropylthiophenol)-2-hydroxyl nicotinamide (12c), which binds Mcl-1 with an IC50 value of 54 nM was obtained. Compound 12c demonstrated a better aqueous solubility than S1.

Substituted 6-phenyl-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyridines

This disclosure describes novel substituted 6-phenyl-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridines and their use as agents for treating anxiety.

Substituted 6-phenyl-1,2,4-triazolo[4,3-a]pyridines

This disclosure describes novel 6-(substituted-phenyl)-1,2,4-triazolo[4,3-a]pyridines useful as hypotensive agents.

Substituted 3-alkyl-6-phenyl-1,2,4-triazolo-[4,3-a]pyridines

This disclosure describes novel 3-alkyl-6-(substituted-phenyl)-1,2,4-triazolo[4,3-a]pyridines useful as anxiolytic agents.