875781-18-3

Usage

Uses

Used in Organic Synthesis:
5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine is utilized as a key building block in organic synthesis for constructing more intricate molecular structures. Its presence of both bromine and iodine atoms allows for a variety of chemical reactions, making it a valuable component in the synthesis of novel compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine is employed as a starting material for the development of new pharmaceuticals. Its unique structure and reactivity enable the creation of potential drug candidates with specific therapeutic properties.
Used as a Reagent in Chemical Reactions:
Due to its distinctive structural features, 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine serves as a reagent in a range of chemical reactions. It facilitates the synthesis of new compounds and contributes to the advancement of chemical research and development.
Used in Pharmaceutical Research and Development:
5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine is being explored for its potential as a drug candidate in pharmaceutical research. Its unique properties and reactivity are being studied for the treatment of various diseases, highlighting its importance in drug discovery and development.
Used in Drug Discovery:
In the industry of drug discovery, 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine is used as a versatile chemical entity for the identification and development of new therapeutic agents. Its potential pharmaceutical applications are being rigorously investigated to bring forth innovative treatments for a multitude of medical conditions.

InChI:InChI=1/C6H3BrIN3/c7-3-1-4-5(8)10-11-6(4)9-2-3/h1-2H,(H,9,10,11)

Upstream product

• 117007-52-0 3-iodo-1H-pyrazolo[3,4-b]pyridine 
• 516-12-1 N-iodo-succinimide 
• 875781-17-2 5-bromo-7-azaindazole 
• 875781-15-0 5-bromo-2-fluoro-3-pyridinecarboxaldehyde 
• 271-73-8 1H-Pyrazolo[3,4-b]pyridine 

Downstream Products

• 916326-31-3 tert-butyl 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate 
• 875639-15-9 5-bromo-3-iodo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine 
• 882029-94-9 5-bromo-3-phenyl-1H-pyrazolo[3,4-b]pyridine 
• 1299607-55-8 tert-butyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate 

Relevant academic research and scientific papers

Lead Optimization of 3,5-Disubstituted-7-Azaindoles for the Treatment of Human African Trypanosomiasis

Neglected tropical diseases such as human African trypanosomiasis (HAT) are prevalent primarily in tropical climates and among populations living in poverty. Historically, the lack of economic incentive to develop new treatments for these diseases has meant that existing therapeutics have serious shortcomings in terms of safety, efficacy, and administration, and better therapeutics are needed. We now report a series of 3,5-disubstituted-7-azaindoles identified as growth inhibitors of Trypanosoma brucei, the parasite that causes HAT, through a high-throughput screen. We describe the hit-to-lead optimization of this series and the development and preclinical investigation of 29d, a potent antitrypanosomal compound with promising pharmacokinetic (PK) parameters. This compound was ultimately not progressed beyond in vivo PK studies due to its inability to penetrate the blood-brain barrier (BBB), critical for stage 2 HAT treatments.

Design and synthesis of 1H-pyrazolo[3,4-b]pyridines targeting mitogen-activated protein kinase kinase 4 (MKK4) - A promising target for liver regeneration

Currently, the therapeutic options for treatment of liver failure are very limited. As mitogen-activated protein kinase kinase 4 (MKK4) has recently been identified by in vivo RNAi experiments to be a major regulator in hepatocyte regeneration, we pursued the development of a small molecule targeting this protein kinase. Starting from the approved BRAFV600E inhibitor vemurafenib (8), that showed a high off-target affinity to MKK4 in an initial screening, we followed a scaffold-hopping approach, changing the core heterocycle from 1H-pyrrolo[2,3-b]pyridine to 1H-pyrazolo[2,3-b]pyridine (10). Affinity to MKK4 could be conserved while the selectivity against off-target protein kinases was slightly improved. Further modifications led to 58 and 59 showing high affinity to MKK4 in the low nanomolar range and excellent selectivity profile from mandatory multiparameter-optimization for the essential anti-targets (MKK7, JNK1) and off-targets (BRAF, MAP4K5, ZAK) in the MKK4 pathway. Herein we report the first selective MKK4 inhibitors in this class.

Synthesis of novel 1H-Pyrazolo[3,4-b]pyridine derivatives as DYRK 1A/1B inhibitors

As DYRK1A and 1B inhibitors, 1H-pyrazolo[3,4-b]pyridine derivatives were synthesized. Mostly, 3-aryl-5-arylamino compounds (6) and 3,5-diaryl compounds (8 and 9) were prepared and especially, 3,5-diaryl compound 8 and 9 showed excellent DYRK1B inhibitory enzymatic activities with IC50 Values of 3–287 nM. Among them, 3-(4-hydroxyphenyl), 5-(3,4-dihydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine (8h) exhibited the highest inhibitory enzymatic activity (IC50 = 3 nM) and cell proliferation inhibitory activity (IC50 = 1.6 μM) towards HCT116 colon cancer cells. Also compound 8h has excellent inhibitory activities in patient-derived colon cancer organoids model as well as in 3D spheroid assay model of SW480 and SW620. The docking study supported that we confirmed that compound 8h binds to DYRK1B through various hydrogen bonding interactions and hydrophobic interactions.

HETEROARYL-SUBSTITUTED PYRAZOLO-PYRIDINE PROTEIN KINASE INHIBITORS FOR PROMOTING LIVER REGENERATION OR REDUCING OR PREVENTING HEPATOCYTE DEATH

The invention relates to pyrazolo-pyridine compounds which inhibit mitogen-activated protein kinase kinase 4 (MKK4) and in particular, selectively inhibit MKK4 over protein kinases JNK1 and MKK7. The compounds are useful for promoting liver regeneration or reducing or preventing hepatocyte death. They are further useful for treating osteoarthritis or rheumatoid arthritis, or CNS-related diseases.

Azaindazole bipyridine derivative myeloid cell proliferation inhibitor as well as preparation method and application thereof in pharmacy

The invention provides an azaindazole bipyridine derivative myeloid cell proliferation inhibitor shown as a formula I, wherein R1, R2 and R3 have the meanings defined in the specification of the invention. A compound in formula I can significantly inhibit proliferation and related disordersof myeloid cells represented by MOLM-16, HL-60, and MV-4-11. The formula I or salt thereof or the related pharmaceutical composition provided by the invention has excellent in-vivo and in-vitro inhibitory activity, good druggability, high bioavailability and no obvious damage to organs. Therefore, the compound shown in the formula I or the salt thereof and the related drug combination have huge clinical application prospects.

IMIDAZOPIPERAZINE INHIBITORS OF TRANSCRIPTION ACTIVATING PROTEINS

The present disclosure relates to heterocyclic compounds and methods which may be useful as inhibitors of transcription activating proteins such as CBP and P300 for the treatment or prevention of diseases such as proliferative diseases, inflammatory disorders, autoimmune diseases, and fibrotic diseases.

PROTEIN KINASE MKK4 INHIBITORS FOR PROMOTING LIVER REGENERATION OR REDUCING OR PREVENTING HEPATOCYTE DEATH

The invention relates to pyrazolo-pyridine compounds which inhibit mitogen-activated protein kinase kinase 4 (MKK4) and in particular, selectively inhibit MKK4 over protein kinases JNK1 and MKK7. The compounds are useful for promoting liver regeneration or reducing or preventing hepatocyte death. They are further useful for treating osteoarthritis or rheumatoid arthritis, or CNS-related diseases.

Alkylene phenylsulfonamide type selective ZAK inhibitor and application thereof

The invention relates to application of an alkylene phenylsulfonamide compound with a structure of formula (I) (shown in the description) or pharmaceutically acceptable salt thereof or stereisomer thereof or a prodrug molecule thereof in preparation of a

PYRAZOLO FUSED HETEROCYCLIC COMPOUNDS AS ERK INHIBITORS

Disclosed herein is a compound of formula (I) and/or a pharmaceutically acceptable salt thereof that can serve as Erk inhibitors. They are potentially useful in the treatment of diseases treatable by inhibition of Erk, such as cancers. Also disclosed here

HETEROCYCLIC COMPOUNDS AS ERK INHIBITORS

Compounds of Formula (I) and pharmaceutical compositions containing the compounds are disclosed, which are used for treatment of disease, disorder or condition associated with ERK activity.