5657-63-6

Usage

Uses

Used in Organic Synthesis:
3-Cyano-2-hydroxypyridine is utilized as a building block in the synthesis of more complex organic compounds. Its structural features make it a valuable intermediate in the creation of a variety of chemical products.
Used in Research and Development:
3-Cyano-2-hydroxypyridine is also employed in research and development settings, where it serves as a starting material for the exploration of new chemical reactions and the synthesis of novel compounds. Its reactivity and structural attributes are of particular interest to scientists in the field of chemistry.
Safety Considerations:
Given its chemical nature, 3-Cyano-2-hydroxypyridine must be handled with care to ensure safety and to prevent any potential hazards associated with its use in chemical processes. Proper safety protocols and procedures should be followed to mitigate risks during its application in both industrial and laboratory settings.

InChI:InChI=1/C6H4N2O/c7-4-5-2-1-3-8-6(5)9/h1-3H,(H,8,9)

Upstream product

• 1986-81-8 nicotinamide N-oxide 
• 108-24-7 acetic anhydride 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 107-91-5 cyanoacetic acid amide 
• 542-78-9 Malondialdehyde 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 

Downstream Products

• 1613435-79-2 7-(4-chlorophenyl)-1-methyl-5-oxo-1,6-naphthyridin-1-ium iodide 
• 1613435-76-9 7-(4-methylphenyl)-1,6-naphthyridin-5-one 1-oxide 
• 1613435-70-3 2-(4-aminophenylethynyl)-3-cyanopyridine 
• 1005161-99-8 7-(4-methoxyphenyl)-5H-pyrano[4,3-b]pyridin-5-one 
• 1613436-07-9 7-(4-chlorophenyl)pyrano[4,3-b]pyridin-5-one 
• 118159-94-7 2-phenylethynylpyridine-3-carbonitrile 
• 5657-54-5 7-Phenyl-5H-pyrano<4,3-b>pyridin-5-one 
• 511240-93-0 7-(4-methylphenyl)-1,6-naphthyridin-5-one 
• 1319736-97-4 7-(4-trifluoromethylphenyl)-1,6-naphthyridin-5-one 
• 511240-96-3 7-(4-chlorophenyl)-1,6-naphthyridin-5-one 
• 1613435-72-5 7-(4-aminophenyl)-1,6-naphthyridin-5-one 
• 1613435-73-6 7-(4-aminophenyl)pyrano[4,3-b]pyridin-5-one 
• 1613435-74-7 7-(4-hydroxyphenyl)-1,6-naphthyridin-5-one 
• 1613435-80-5 7-(4-aminophenyl)-1-methyl-5-oxo-1,6-naphthyridin-1-ium iodide 

Relevant academic research and scientific papers

Pyrazolopyridine or indazole derivatives as protein kinase inhibitors

The present invention relates to novel pyrazolopyridine or indazole derivatives having inhibitory activity against protein kinases or pharmaceutically acceptable salts thereof. Since compounds of the present invention have excellent inhibitory activity against to protein kinases, for example, ABL, ACK1, ALK, Aurora A, Aurora B, Aurora C, BLK, BMX/ETK, BRSK1, BTK, c-Src, CAMKK, CDK1, CDK2, CDK5, CLK, DDR, DYRK1B, EPHA, EPHB, FAK/PTK2, FER, FES/FPS, FGFR, FGR, FLT3, FLT4/VEGFR3, FMS, FRK/PTK5, FYN, GSK3b, HCK, IGF1R, IR, IRAK1, IRR/INSRR, ITK, JAK2, KHS/MAP4K5, LCK, LYN, PHKg, PLK4/SAK, PYK2, RET, ROS/ROS1, TIE2/TEK, TRK, TXK, TYK, YES/YES1, and the like, the compounds are useful for treatment and prevention of various kinds of cancer diseases.

Design and synthesis of novel substituted naphthyridines as potential c-Met kinase inhibitors based on MK-2461

Abstract Two series of novel 1,5-naphthyridine and 1,6-naphthyridine derivatives were designed and synthesized based on the c-Met kinase inhibitor MK-2461 under the guidance of scaffold hopping strategy. All were tested on c-Met kinase and in vitro anti-tumor activities against Hela and A549 cell lines. The results indicated that 1,6-naphthyridine was a more promising c-Met inhibitory structure core compared with 1,5-naphthyridine. Among them, 26b and 26c showed the best enzymic and cytotoxic activities. The western blot experiments implied that the cytotoxic activity of 26c might be partially through suppressing the phosphorylation of c-Met kinase.

Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.

2-Amino-5-aryl-pyridines as selective CB2 agonists: Synthesis and investigation of structure-activity relationships

2-Amino-5-aryl-pyridines, exemplified by compound 1, had been identified as a synthetically tractable series of CB2 agonists from a high-throughput screen of the GlaxoSmithKline compound collection. Described herein are the results of an investigation of the structure-activity relationships (SAR) which led to the identification a number of potent and selective agonists.

Hetero-Diels-Alder reaction of propenenitriles with enol ethers: A convenient approach to functionalized 3,4-dihydro-2H-pyrans

The hetero-Diels-Alder reaction of 3-(N-acetyl-N-benzylamino)-2-formylprop- 2-enenitrile with enol ethers yielded cis/trans diastereoisomers of 2-alkoxy-4-amino-3,4-dihydro-2H-pyran-5-carbonitriles in moderate yields. Acidic hydrolysis of cis-diastereoisomer in concentrated sulfuric acid gave 2-oxo-1,2-dihydropyrydine-3-carbaldehyde. The reaction of 2-benzoyl-3- heteroaromaticprop-2-enenitriles with enol ethers afforded diastereoisomeric cis/trans cycloadducts in good yields. The structure of the products is discussed in terms of configuration and preferred conformation.

The Semmler-Wolff Aromatization and Schmidt Reaction Applied to Some Pyridopyrazolobenzotriazines

Pyridopyrazolobenzotriazin-4(1H)ones were transformed via their oximes in a Semmler-Wolff aromatization process in the tetracyclic heteroaromatic amines 4 or by Schmidt reaction into a mixture of the same amine 4 and a ring enlarg

Reaction of N-(2-Pyridylmethyl)-3,5-dimethylbenzamide and N-(3-Pyridylmethyl)-3,5-dimethylbenzamide N-Oxides with Acetic Anhydride

As a continuation of our work on the reaction of N-pyridylmethyl-3,5-dimethylbenzamide N-oxides with acetic anhydride, we now report a study of the reaction of N-(2-pyridylmethyl)-3,5-dimethylbenzamide N-oxide (5) and N-(3-pyridylmethyl)-3,5-dimethylbenzamide N-oxide (6) with acetic anhydride.Compound 5 gave N,N'-di(3,5-dimethylbenzoyl)-1,2-di(2-pyridyl)ethenediamine (7) and 3,5-dimethylbenzamide (8).Compound 6 afforded three products formulated as 2-acetoxy-3-(3,5-dimethylbenzoylaminomethyl)pyridine (12), 3-(3,5-dimethylbenzoylaminomethyl)-2-pyridone (13) and 5-(3,5-dimethylbenzoylaminomethyl)-2-pyridone (14).Analytical and spectral data are presented which support the structures proposed.