405224-22-8

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-3-cyano-2-hydroxypyridine is used as a building block for the production of pharmaceutical drugs. Its unique structure allows for various chemical reactions and synthesis processes, making it a valuable component in the development of new and effective medications.
Used in Agrochemical Industry:
In the agrochemical industry, 5-Bromo-3-cyano-2-hydroxypyridine is used as a key intermediate in the synthesis of agrochemicals. Its versatility and reactivity enable the creation of compounds with specific properties, such as herbicides, insecticides, and fungicides, to improve crop protection and yield.
Used in Chemical Research and Development:
5-Bromo-3-cyano-2-hydroxypyridine is also used as a substrate in chemical research and development. Its unique structure and reactivity make it an ideal candidate for studying various chemical reactions and exploring new synthesis pathways, ultimately contributing to the advancement of science and technology in the field of chemistry.

InChI:InChI=1/C6H3BrN2O/c7-5-1-4(2-8)6(10)9-3-5/h1,3H,(H,9,10)

Upstream product

• 20577-27-9 pyrid-2-one-3-carbonitrile 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 20577-27-9 2-hydroxy-3-cyanopyridine 

Downstream Products

• 405224-23-9 5-bromo-2-chloropyridine-3-carbonitrile 
• 1083168-85-7 methyl 2-(5-bromo-3-cyano-2-oxopyridin-1(2H)-yl)acetate 
• 1083168-86-8 methyl 2-(3-cyano-2-oxo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-1(2H)-yl) acetate 
• 1083167-61-6 methyl 2-(3-cyano-5-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)-2-oxopyridin-1(2H)-yl)acetate 
• 35982-98-0 C₁₂H₇ClN₂O 
• 1426959-54-7 C₁₈H₁₂N₂O 
• 1426959-48-9 C₁₂H₈N₂OS 
• 1426959-49-0 C₁₃H₁₀N₂OS 
• 1426959-50-3 C₁₅H₁₄N₂OS 
• 1426959-51-4 C₁₇H₁₈N₂OS 
• 1426959-52-5 C₁₂H₇BrN₂OS 
• 1426959-53-6 C₁₂H₉N₃OS 
• 1426959-55-8 C₂₂H₂₀N₂OS 

Relevant academic research and scientific papers

Identification of 1H-pyrazolo[3,4-b]pyridine derivatives as potent ALK-L1196M inhibitors

Anaplastic lymphoma kinase (ALK) has been recognised as a promising molecular target of targeted therapy for NSCLC. We performed SAR study of pyrazolo[3,4-b]pyridines to override crizotinib resistance caused by ALK-L1196M mutation and identified a novel and potent L1196M inhibitor, 10g. 10g displayed exceptional enzymatic activities (50) against ALK-L1196M as well as against ALK-wt. In addition, 10g is an extremely potent inhibitor of ROS1 (50) and displays excellent selectivity over c-Met. Moreover, 10g strongly suppresses proliferation of ALK-L1196M-Ba/F3 and H2228 cells harbouring EML4-ALK via apoptosis and the ALK signalling blockade. The results of molecular docking studies reveal that, in contrast to crizotinib, 10g engages in a favourable interaction with M1196 in the kinase domain of ALK-L1196M and hydrogen bonding with K1150 and E1210. This SAR study has provided a useful insight into the design of novel and potent inhibitors against ALK gatekeeper mutant.

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.

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.

Discovery of novel CDK inhibitors via scaffold hopping from CAN508

Cyclin-dependent kinases (CDKs) are promising drug targets for various human diseases, especially for cancers. Scaffold hopping strategy was applied on CAN508, a known selective CDK9 inhibitor, and a series of pyrazolo[3,4-b]pyridine compounds were synthe

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.

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.

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.

A Casein kinase 1/Checkpoint kinase 1 pyrazolo-pyridine protein kinase inhibitor as novel activator of the p53 pathway

Reactivation of the wild-type p53 pathway is one key goal aimed at developing targeted therapeutics in the cancer research field. Although most p53 protein kinases form 'p53-activating' signals, there are few kinases whose action can contribute to the inhibition of p53, as Casein kinase 1 (CK1) and Checkpoint kinase 1 (CHK1). Here we report on a pyrazolo-pyridine analogue showing activity against both CK1 and CHK1 kinases that lead to p53 pathway stabilisation, thus having pharmacological similarities to the p53-activator Nutlin-3. These data demonstrate the emerging potential utility of multivalent kinase inhibitors.

Design and synthesis of 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and pyrazolo[3,4-b]pyridines for Aurora-A kinase inhibitors

Two series of 3-aminopyrazole compounds including 24 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and 16 pyrazolo[3,4-b]pyridines were synthesized and evaluated against HCT116, A549, and A2780 tumor cell lines. Among them, three compounds were found to have the ideal anti-proliferative activities in vitro. Docking experiments showed that the novel pyrazolo[3,4-b]pyridines share the similar interaction mode with Aurora-A kinase as PHA739358.

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.