102249-52-5

Usage

Uses

Used in Pharmaceutical Research:
2,4-Dihydroxy-5-phenylpyridine is used as a research tool for studying the role of reactive oxygen species and oxidative stress in cells and tissues. Its ability to inhibit key enzymes involved in these processes makes it valuable in understanding the underlying mechanisms of various diseases and conditions.
Used in Anticancer Applications:
In the field of oncology, 2,4-Dihydroxy-5-phenylpyridine is utilized as a potential anticancer agent. Its capacity to disrupt electron transport in cancer cells can lead to the inhibition of their growth and proliferation, making it a candidate for further development in cancer treatment strategies.
Used in Antimicrobial Applications:
2,4-Dihydroxy-5-phenylpyridine also serves as a potential antimicrobial agent, where its inhibitory effects on enzymes can be leveraged to combat microbial infections. This application is particularly relevant in the ongoing search for new antimicrobial compounds to address the growing issue of antibiotic resistance.
Used in Laboratory and Industrial Settings:
While its potential toxicity is a concern, 2,4-Dihydroxy-5-phenylpyridine is still used in various laboratory and industrial applications due to its unique properties. Careful handling and safety measures are paramount to ensure the safe use of 2,4-Dihydroxy-5-phenylpyridine in these settings.

Upstream product

• 102249-51-4 2,4-dihydroxy-3-ethoxycarbonyl-5-phenylpyridine 
• 135959-07-8 α-(aminomethyl)benzeneacetic acid,ethyl ester 
• 17838-69-6 ethyl 3-oxo-2-phenylpropanoate 
• 32265-03-5 6-chloro-4-hydroxy-5-phenyl(1H)-pyridin-2-one 
• 140-29-4 phenylacetonitrile 

Downstream Products

• 101582-43-8 5-phenyl-3,3-dipropyl-1H-pyridine-2,4-dione 
• 102249-53-6 2,4-dibromo-5-phenylpyridine 
• 1415714-08-7 C₂₂H₂₃NO₉ 
• 1415714-18-9 C₁₆H₁₇NO₆ 
• 756499-69-1 2-(4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-yl)propionic acid 
• 756499-58-8 ethyl 2-(4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-yl)propionate 
• 756499-57-7 ethyl 3-(4-chlorophenylsulfanyl)-2-(4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-yl)propionate 
• 1115195-47-5 C₂₀H₂₁NO₂ 

Relevant academic research and scientific papers

Total synthesis of (±)-leporin A

An efficient synthesis of (±)-leporin A (1) has been developed using a tandem Knoevenagel condensation-inverse electron demand intramolecular hetero Diels-Alder reaction to construct the key tricyclic intermediate 3 from pyridone 5 and dienal 6 in one pot in 35% yield. Hydroxylation (71%) of 3 and methylation (77%) of the resulting hydroxypyridone 2 completed the first total synthesis of (±)-leporin A (1).

Synthesis and antifungal activity of polycyclic pyridone derivatives with anti-hyphal and biofilm formation activity against Candida albicans

Thirty-five pyridone derivatives were synthesized, with derivatization conducted on polycyclic pyridone scaffolds, including cis- or trans-oxydecalin and other cyclic structures, by domino-Knoevenagel-electrocyclic reactions. The anti-fungal activities of the synthesized compounds were tested against Candida albicans. Ten compounds inhibited hyphal formation without inhibiting growth. Pyridones with anti-hyphal formation activity (4c, 6d, 12a and 12c) were tested for their ability to inhibit biofilm formation. Compound 6d showed both anti-hyphal and biofilm inhibition activity.

Practical Pd/C-catalysed suzuki-miyaura reactions for the preparation of 3-aryl-4-oxypyridin-2(1H)-ones, 3-aryl-2,4-oxypyridines and 3-aryl-2,4- oxyquinolines as useful intermediates for the synthesis of biologically active compounds

Practical heterogeneous Pd/C-catalysed Suzuki-Miyaura cross-coupling reactions of 3-iodo-4-oxypyridin-2(1H)-ones, 3-iodo-2,4-oxypyridines, and 3-iodo-2,4-oxyquinolines with arylboronic acids are described as a useful and efficient alternative to homogeneous conditions. The methodology features ligand-free and environmentally friendly conditions, and tolerates a wide range of boronic acids. The cross-coupled products can be viewed as useful intermediates for the preparation of 3-aryl-4-hydroxypyridin-2(1H)-ones, which can be used as new nucleobases for antiherpetic agents.

PYRIDONE GPR119 G PROTEIN-COUPLED RECEPTOR AGONISTS

Novel compounds are provided which are GPR119 G protein-coupled receptor modulators. GPR119 G protein-coupled receptor modulators are useful in treating, preventing, or slowing the progression of diseases requiring GPR 119 G protein-coupled receptor modulator therapy. These novel compounds have the structure Formula I or Formula IA.

Synthesis and evaluation of the antitumor agent TMC-69-6H and a focused library of analogs

A concise, efficient and flexible total synthesis of the potent antitumor agent TMC-69-6H (2) is described. Key steps involve the palladium catalyzed regioselective addition of 4-hydroxy-2-pyridone 5 to pyranyl acetate 6 which is accompanied by a spontaneous 1,4-addition of the phenolic -OH group to the emerging enone to give the tricyclic product 7 in excellent yield. When this reaction is carried out with optically enriched (S)-6 (conveniently prepared by a lipase catalyzed kinetic dynamic resolution) in the presence of the chiral ligand (S,S)-12 and allylpalladium chloride dimer, the ensuing matched situation delivers the key building block (-)-7 in 96% ee. Its further elaboration into 2 involves a Julia-Kocienski olefination with tetrazolylsulfone 19 and a final N-oxidation effected by the peroxomolybdenum complex [(pyridine)MoO 5(HMPA)] to form the hydroxamic acid motif. The flexibility inherent to this route allows for the preparation of a focused library of analogues for biochemical evaluation. The results obtained show that N-hydroxy-2-pyridone derivatives constitute a promising new class of selective phosphatase inhibitors. In contrast to previous reports in the literature, however, TMC-69-6H and congeners are found to exhibit pronounced activities against the tyrosine protein phosphatase PTB1B, the dual specific phosphatase VHR, and the serine/threonine phosphatase PP1, while being only weak inhibitors for the dual specific phosphatases Cdc25 A and B. Two key intermediates of the synthesis route have been characterized by X-ray crystallography. Graphical Abstract.

Reactivity of Some 3-Substituted Derivatives of 2,6-Dihalogenopyridines Towards Potassium Amide in Liquid Ammonia .

Reactions of 2,6-dichloro-3-phenyl-, 2,6-dibromo-3-phenyl-, 2,6-dichloro-3-dimethylamino- and 2,6-dibromo-3-dimethylaminopyridine with potassium amide in liquid ammonia were investigated.Whereas 2,6-dichloro-3-phenylpyridine yields 4-amino-2-benzylpyrimidine, from 2,6-dibromo-3-phenylpyridine as a product of a novel ring fission 2-amino-1-cyano-1-phenyl-but-1-en-3-yne was isolated, together with 4-amino-6-bromo-3-phenylpyridine and 2,6-diamino-3-phenylpyridine.It was shown that neither 2-amino-6-bromo-3-phenyl- nor 6-amino-2-bromo-3-phenylpyridine are intermediates in the formation of the 2,6-diamino derivative, as these bromo compounds are transformed in the basic medium into 1,3-dicyano-1-phenylpropene.From both 2,6-dichloro-3-dimethylamino- and 2,6-dibromo-3-dimethylaminopyridine mixtures are obtained from which only 2-amino-1-cyano-1-dimethylamino-but-1-en-3-yne and 4-amino-6-halogeno-3-dimethylaminopyridine were isolated.Mechanisms for the reactions studied are proposed, i.e. a SN(ANRORC) mechanism for the aminodebromination of 2,6-dibromo-3-phenylpyridine into the corresponding 2,6-diamino compound.