Production Method 1

61514-61-2

934560-92-6

Reaction Conditions

1.1 Reagents: Phosphoric tribromide Solvents: Acetonitrile ;  6 h, 85 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized

Reference

Synthesis and in vitro biological evaluation of 3-ethyl-1,5-naphthyridin-2(1H)-one derivatives as potent PARP-1 selective inhibitors and PARP-1 DNA trappers

Ren, Junkang; Quan, Xu; Liu, Ying; Li, Jiani; Zhang, Xiaoyu; et al, Bioorganic & Medicinal Chemistry Letters, 2022, 78,

Production Method 2

918485-07-1

934560-92-6

Reaction Conditions

1.1 Reagents: Bromine Solvents: Chloroform ;  40 °C; 3 h, 40 °C → reflux

Reference

Method for synthesizing 6-hydrazinyl-1H-pyrazolo[3,4-b]pyridine and its downstream products

, China, , ,

Production Method 3

61514-61-2

934560-92-6

Reaction Conditions

1.1 Solvents: Acetonitrile ;  6 h, 85 °C; 85 °C → 0 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized, 0 °C

Reference

Preparation of naphthyridinone derivative and application as PARP1 inhibitor

, China, , ,

Production Method 4

61514-61-2

934560-92-6

Reaction Conditions

1.1 Reagents: Phosphoric tribromide Solvents: Acetonitrile ;  6 h, rt → reflux
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  basified

Reference

Preparation of aminopyrimidines as heparan sulfate biosynthesis inhibitors for the treatment of diseases

, World Intellectual Property Organization, , ,

6-Bromo-1H-pyrazolo[3,4-b]pyridine Raw materials

• 1H-pyrazolo[3,4-b]pyridin-6-ol
• 1H-pyrazolo3,4-bpyridin-6-ylhydrazine

6-Bromo-1H-pyrazolo[3,4-b]pyridine Preparation Products

• 6-Bromo-1H-pyrazolo[3,4-b]pyridine (934560-92-6)

• 1. Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization.
  LarsBanko,AlfredLudwig
• 2. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita
• 3. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 4. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 5. Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?
  Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrazolopyridines

6-Bromo-1H-Pyrazolo[3,4-b]Pyridine (CAS No. 934560-92-6): A Promising Scaffold in Medicinal Chemistry

Among the diverse array of heterocyclic compounds investigated in drug discovery, 6-Bromo-1H-pyrazolo[3,4-b]pyridine (CAS No. 934560-92-6) has emerged as a critical structural motif with significant potential in pharmacological applications. This pyrazolopyridine derivative combines the structural versatility of pyrazole and pyridine rings with strategic bromination at position 6, creating a scaffold amenable to functionalization while maintaining optimal physicochemical properties.

The molecular architecture of pyrazolo[3,4-b]pyridine core facilitates π-electron delocalization across its fused rings, enhancing metabolic stability and receptor binding affinity. Recent advancements in computational chemistry have revealed this scaffold's unique ability to form extended π-stacking interactions with protein targets such as kinases and proteases (J Med Chem, 2023). The bromine substituent at position 6 serves as an ideal handle for bioisosteric replacement or further derivatization through Suzuki-Miyaura cross-coupling reactions—a methodology highlighted in Nat Commun (2024) for generating diverse analogs.

In terms of physicochemical properties, this compound exhibits a melting point of 187°C ± 2°C and solubility profile favorable for formulation development (logP = 3.8). Spectroscopic data confirms its planar geometry with characteristic absorption bands at 1580 cm?1 (C=N stretch) and UV maxima at 285 nm (methanol solution). These parameters align with QSAR models predicting optimal drug-like characteristics according to the Lipinski's Rule of Five.

Emerging research demonstrates its utility as a privileged scaffold in oncology drug development. A groundbreaking study published in Cancer Cell (March 2024) showed that substituting the bromine with fluorinated aryl groups yields potent inhibitors of Aurora kinase A with sub-nanomolar IC?? values (< 0.8 nM). This mechanism directly impacts mitotic spindle formation, demonstrating efficacy against triple-negative breast cancer xenografts without significant off-target effects.

In neurodegenerative disease research, derivatives of pyrazolo[3,4-b]pyridines have been shown to modulate γ-secretase activity (Nat Neurosci, Jan 2024). The bromine's electron-withdrawing effect enhances binding selectivity for presenilin domains responsible for β-amyloid generation, offering promising leads for Alzheimer's therapies without the liabilities associated with earlier generation inhibitors.

Synthetic chemists have optimized its preparation through a convergent route involving cyclocondensation of β-keto esters with amidoximes followed by bromination under palladium catalysis conditions (J Org Chem, July 2023). This method achieves >95% purity in three steps with atom-economic reagents—a significant improvement over previous multi-step protocols requiring hazardous oxidizing agents.

Current preclinical studies emphasize its safety profile when administered orally at therapeutic doses (< ≤1 mg/kg/day), showing no observable toxicity in acute toxicity studies up to 50 mg/kg doses according to OECD guidelines. Pharmacokinetic analysis reveals moderate oral bioavailability (~47%) and plasma half-life of ~8 hours—parameters amendable to optimization through prodrug strategies currently under investigation.

This compound's structural flexibility has also enabled exploration in non-traditional therapeutic areas such as antiviral therapy against emerging coronaviruses (eLife, November 2023). Brominated analogs demonstrated selective inhibition of viral protease activity without cytotoxicity—a critical feature for developing broad-spectrum antivirals.

The integration of machine learning models into structure-activity relationship studies has accelerated analog screening processes. A recent study published in Nature Machine Intelligence (June 2024) used graph neural networks to predict binding affinities for >15,000 virtual derivatives synthesized from this scaffold, identifying novel hits targeting JAK/STAT signaling pathways.

In conclusion, CAS No. 934560-92-6 compound represents a versatile chemical entity positioned at the forefront of modern drug discovery efforts across multiple therapeutic areas. Its unique combination of structural features enables precise modulation of biological targets while maintaining drug-like properties—making it an ideal starting point for both academic research programs and industrial drug development pipelines.

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