20577-27-9

Usage

Uses

Used in Organic Synthesis:
2-Hydroxy-3-cyanopyridine is used as a synthetic building block for the development of complex organic molecules. Its unique structure, which includes a hydroxyl and a cyano group attached to a pyridine ring, allows it to participate in a wide range of chemical reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Hydroxy-3-cyanopyridine is used as a key intermediate in the synthesis of various drug candidates. Its presence in the molecular structure can contribute to the desired biological activity, such as enhancing the drug's potency, selectivity, or stability.
Used in Agrochemical Industry:
2-Hydroxy-3-cyanopyridine also finds application in the agrochemical industry, where it is employed as a starting material for the synthesis of novel pesticides, herbicides, and other crop protection agents. Its incorporation into these molecules can lead to improved efficacy and selectivity, ultimately benefiting agricultural productivity and sustainability.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 2-Hydroxy-3-cyanopyridine is used as a precursor for the synthesis of various dyes and pigments. Its dark yellow solid form can be further modified to produce a range of colors, which can be utilized in the textile, plastics, and printing industries.
Used in Research and Development:
2-Hydroxy-3-cyanopyridine is also used in research and development settings, where it serves as a valuable tool for understanding the fundamental chemical properties and reactivity patterns of similar compounds. Its study can lead to the discovery of new synthetic routes, applications, and insights into the broader field of organic chemistry.

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

Upstream product

• 110-89-4 piperidine 
• 5444-80-4 1,3,3-triethoxypropene 
• 107-91-5 cyanoacetic acid amide 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 1986-81-8 nicotinamide N-oxide 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 542-78-9 Malondialdehyde 
• 108-24-7 acetic anhydride 
• 3939-13-7 3-cyano-2-fluoropyridine 
• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 14906-64-0 3-cyanopyridine N-oxide 

Downstream Products

• 766515-33-7 3-cyano-2-hydroxy-5-iodopyridine 
• 766515-34-8 2-chloro-5-iodopyridine-3-carbonitrile 
• 766515-35-9 1-methyl-3-amino-5-iodo-1H-pyrazolo[3,4-b]pyridine 
• 766515-42-8 1-methyl-3-amino-5-phenylethynyl-1H-pyrazolo[3,4-b]pyridine 
• 766515-45-1 1-methyl-3-iodo-5-phenylethynyl-1H-pyrazolo[3,4-b]pyridine 
• 766515-40-6 1-methyl-3-(2,2-dimethyl-propionamido)-5-phenyl-1H-pyrazolo[3,4-b]pyridine 
• 766515-39-3 (E)-1-methyl-3-(2,2-dimethyl-propionamido)-5-styryl-1H-pyrazolo[3,4-b]pyridine 
• 766515-38-2 1-methyl-3-(2,2-dimethyl-propionamido)-5-phenylethynyl-1H-pyrazolo[3,4-b]pyridine 
• 405224-22-8 2-hydroxy-3-cyano-5-bromopyridine 
• 1372179-92-4 1-{[(6S,7R)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]methyl}-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2(1H)-one monohydrochloride 
• 1372186-94-1 tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[2-oxo-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-1(2H)-yl]methyl}-1,4-oxazepane-4-carboxylate 
• 1372180-08-9 3-(1-(((6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl)methyl)-2-oxo-1,2-dihydropyridin-3-yl)-1,2,4-oxadiazol-5(4H)-one hydrochloride 
• 1372187-15-9 (6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((2-oxo-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 

Relevant academic research and scientific papers

Pyrazolopyridine hydroxamic acid compound as well as preparation method and application thereof

The invention relates to the technical field of chemical synthesis, in particular to a pyrazolopyridine hydroxamic acid compound as well as a preparation method and application thereof. The pyrazolopyridine hydroxamic acid compound comprises a compound as shown in a formula (1), an isomer thereof, and a hydrate thereof or a pharmaceutically acceptable salt thereof, wherein n is an integer, and R is any one of a substituted or unsubstituted aromatic ring group and a substituted alkyl group. The compound can well inhibit cancer cell proliferation, and then has an excellent treatment effect on tumors.

Preparation method of 2- novel chloronicotinic acid (by machine translation)

The method disclosed by the invention 2 - comprises the following steps: reacting the obtained :1) product with trichlorooxygen phosphorus, in the presence of 1) an acid, to give 2 - the product of 2 - the present invention ;2) in the following steps: reacting the obtained product with phosphorus oxychloride, in 2 - the presence of a ;3) base with 2) phosphorus oxychloride in the presence of a base, 2 - 2 . (by machine translation)

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.

A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives

A highly efficient and green method has been developed for the rapid preparation of highly functionalized isoxazolopyridin-3-amine derivatives in excellent yields. This process has a broad substrate scope, is operationally simple, and generally requires no chromatographic purification. In addition, the process is scalable and significantly greener than current alternatives with a PMI of 18 and water as the reaction solvent.

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.

PYRIDYL COMPOUND SUITABLE FOR THE TREATMENT OF METABOLIC DISORDERS

The description relates to a pyridyl compound of Formula 1 wherein A, B, X, R1, R2, R3, R4, R5, R6, and n are as defined in the specification, in all their isotopic forms, stereoisomeric and tautomeric forms and mixtures thereof in all ratios, their pharmaceutically acceptable salts, N-oxides, pharmaceutically acceptable solvates, isosteres and prodrugs thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia. The description also relates to a process for the manufacture of the pyridyl compound and a pharmaceutical composition containing the pyridyl compound.

Discovery of dual death-associated protein related apoptosis inducing protein kinase 1 and 2 inhibitors by a scaffold hopping approach

DRAK2 emerged as a promising drug target for the treatment of autoimmune diseases and to prevent graft rejection after organ transplantation. Screening of a compound library in a DRAK2 binding assay led to the identification of an isothiazolo[5,4-b]pyridine derivative as a novel ligand for DRAK2, displaying a Kdvalue of 1.6 μM. Subsequent medicinal chemistry work led to the discovery of a thieno[2,3-b]pyridine derivative with strong DRAK2 binding affinity (Kd= 9 nM). Moreover, this compound also behaves as a functional inhibitor of DRAK2 enzymatic activity, displaying an IC50value of 0.82 μM, although lacking selectivity, when tested against DRAK1. This paper describes for the first time functionally active dual DRAK1 and DRAK2 inhibitors that can be used as starting point for the synthesis of chemical tool compounds to study DRAK1 and DRAK2 biology, or they can be considered as hit compounds for hit-to-lead optimization campaigns in drug discovery programs.

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.