Production Method 1

623-47-2

2459-09-8

876379-79-2

Reaction Conditions

1.1 Reagents: O-(3,4-Dinitrophenyl)hydroxylamine Solvents: Dimethylformamide ;  overnight, 40 °C; 40 °C → rt
1.2 Reagents: Potassium carbonate ;  16 h, rt
2.1 Reagents: Sulfuric acid Solvents: Water ;  16 h, 100 °C; 100 °C → rt
2.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 5, cooled
3.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  30 min, 0 °C; 30 °C → rt; 30 min, rt
3.2 Solvents: Water ;  30 min, cooled

Reference

A Cryptosporidium PI(4)K inhibitor is a drug candidate for cryptosporidiosis

Manjunatha, Ujjini H.; et al, Nature (London, 2017, 546(7658), 376-380

Production Method 2

104468-87-3

876379-79-2

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  30 min, 0 °C; 30 °C → rt; 30 min, rt
1.2 Solvents: Water ;  30 min, cooled

Reference

A Cryptosporidium PI(4)K inhibitor is a drug candidate for cryptosporidiosis

Manjunatha, Ujjini H.; et al, Nature (London, 2017, 546(7658), 376-380

Production Method 3

1101120-00-6

876379-79-2

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  16 h, 100 °C; 100 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 5, cooled
2.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  30 min, 0 °C; 30 °C → rt; 30 min, rt
2.2 Solvents: Water ;  30 min, cooled

Reference

A Cryptosporidium PI(4)K inhibitor is a drug candidate for cryptosporidiosis

Manjunatha, Ujjini H.; et al, Nature (London, 2017, 546(7658), 376-380

3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid Raw materials

• 3-Ethyl 5-methyl pyrazolo[1,5-a]pyridine-3,5-dicarboxylate
• ethyl propiolate
• Methyl isonicotinate
• pyrazolo[1,5-a]pyridine-5-carboxylic acid

3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid Preparation Products

• 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (876379-79-2)

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• 5. Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4?
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Introduction to 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic Acid (CAS No. 876379-79-2)

3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid, with the CAS number 876379-79-2, is a significant compound in the field of pharmaceutical chemistry and medicinal research. This heterocyclic compound belongs to the pyrazolo[1,5-a]pyridine class, which has garnered considerable attention due to its versatile biological activities and potential applications in drug development.

The structure of 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid consists of a fused bicyclic system containing a bromine substituent at the 3-position and a carboxylic acid group at the 5-position. This unique arrangement of functional groups makes it a valuable intermediate in synthetic chemistry, particularly in the preparation of more complex molecules with therapeutic properties.

In recent years, there has been growing interest in pyrazolo[1,5-a]pyridine derivatives due to their demonstrated efficacy in various pharmacological assays. The bromine atom in 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid serves as a reactive handle for further functionalization, enabling the synthesis of a wide range of derivatives with tailored biological activities. This flexibility has made it a popular choice for medicinal chemists seeking to develop novel compounds for treating diverse diseases.

One of the most compelling aspects of 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid is its potential as an anti-inflammatory agent. Several studies have highlighted its ability to modulate inflammatory pathways by interacting with specific enzymes and receptors. For instance, research has shown that derivatives of this compound can inhibit the activity of cyclooxygenase-2 (COX-2), a key enzyme involved in the production of prostaglandins that mediate inflammation.

Furthermore, 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid has shown promise in the development of anticancer agents. Its ability to interfere with critical cellular processes such as proliferation and apoptosis makes it a promising candidate for further investigation. Preclinical studies have demonstrated that certain derivatives can induce apoptosis in cancer cells while sparing healthy cells, suggesting a high therapeutic index.

The carboxylic acid group in 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid also provides opportunities for further chemical modification. It can be used to form esters, amides, or other derivatives that may enhance solubility or bioavailability. These modifications are crucial for optimizing pharmacokinetic properties and improving drug delivery systems.

In addition to its pharmaceutical applications, 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid has found utility in materials science and agrochemical research. Its unique structural features make it a valuable building block for synthesizing advanced materials with specific electronic or optical properties. Moreover, its derivatives have shown potential as intermediates in the development of novel pesticides and herbicides.

The synthesis of 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid typically involves multi-step organic reactions starting from readily available precursors. The bromination step is particularly critical and requires careful optimization to ensure high yield and selectivity. Advances in synthetic methodologies have enabled more efficient and sustainable production processes, making this compound more accessible for research and industrial applications.

Ongoing research continues to uncover new applications and mechanisms of action for 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid. For example, recent studies have explored its potential role in neurodegenerative diseases by investigating its effects on neurotransmitter systems. These findings suggest that this compound may have therapeutic benefits beyond its established applications in inflammation and cancer.

The development of novel drug candidates is an iterative process that relies on the availability of high-quality intermediates like 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid. Its versatility and reactivity make it an indispensable tool for medicinal chemists seeking to discover new treatments for unmet medical needs. As research progresses, it is likely that even more innovative applications will be uncovered.

In conclusion, 3-Bromopyrazolo[1,5-a]pyridine-5-carboxylic acid(CAS No. 876379-79-2) is a multifaceted compound with significant potential in pharmaceuticals, materials science, and agrochemicals. Its unique structural features and reactivity make it a valuable intermediate for synthesizing complex molecules with diverse biological activities. Continued research into this compound promises to yield new insights and applications that will benefit society.

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• 1356144-48-3(4-Bromopyrazolo[1,5-a]pyridine-3-carboxylic acid)
• 1345121-19-8(Methyl 6-bromo-5-methylpyrazolo[1,5-a]pyridine-3-carboxylate)
• 55899-30-4(Ethyl 6-bromopyrazolo[1,5-a]pyridine-3-carboxylate)
• 1062368-70-0(Methyl 6-bromopyrazolo[1,5-A]pyridine-3-carboxylate)
• 1211596-19-8(6-Bromopyrazolo[1,5-a]pyridine-3-carboxylic acid)
• 1101121-05-4(5-Bromopyrazolo[1,5-a]pyridine-3-carboxylic acid)
• 104468-87-3(pyrazolo[1,5-a]pyridine-5-carboxylic acid)