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Introduction to 5-Bromo-3-propyl-1H-indazole (CAS No. 1197943-62-6)

5-Bromo-3-propyl-1H-indazole (CAS No. 1197943-62-6) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique structural features, has shown promising potential in various biological and therapeutic applications. In this comprehensive introduction, we will delve into the chemical properties, synthesis methods, biological activities, and recent research advancements associated with 5-Bromo-3-propyl-1H-indazole.

Chemical Structure and Properties

5-Bromo-3-propyl-1H-indazole is a substituted indazole derivative, featuring a bromine atom at the 5-position and a propyl group at the 3-position. The indazole core is a heterocyclic aromatic compound consisting of a pyrazole ring fused to a benzene ring. The presence of the bromine substituent imparts unique electronic and steric properties to the molecule, making it an attractive candidate for various chemical and biological studies.

The molecular formula of 5-Bromo-3-propyl-1H-indazole is C₁₀H₁₂BrN₂, with a molecular weight of approximately 240.12 g/mol. It is typically obtained as a white crystalline solid and is soluble in common organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and methanol. The compound exhibits good thermal stability and can be stored under standard laboratory conditions.

Synthesis Methods

The synthesis of 5-Bromo-3-propyl-1H-indazole can be achieved through several well-established routes in organic chemistry. One common method involves the reaction of 3-bromoaniline with propionitrile in the presence of an acid catalyst, followed by cyclization to form the indazole core. Another approach involves the condensation of 3-bromobenzaldehyde with hydrazine hydrate, followed by reaction with propionitrile to form the desired product.

A recent study published in the Journal of Organic Chemistry reported an efficient one-pot synthesis of 5-Bromo-3-propyl-1H-indazole using microwave-assisted conditions. This method not only reduces reaction time but also improves yield and purity, making it a preferred choice for large-scale production.

Biological Activities

5-Bromo-3-propyl-1H-indazole has been extensively studied for its biological activities, particularly in the context of its potential as a therapeutic agent. One of the key areas of interest is its ability to modulate various signaling pathways involved in cellular processes such as proliferation, apoptosis, and inflammation.

A study published in Bioorganic & Medicinal Chemistry Letters demonstrated that 5-Bromo-3-propyl-1H-indazole exhibits potent anti-inflammatory properties by inhibiting the production of pro-inflammatory cytokines such as TNF-α and IL-6. This makes it a promising candidate for the treatment of inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

In addition to its anti-inflammatory effects, 5-Bromo-3-propyl-1H-indazole has shown promising anticancer activity. Research conducted at the National Cancer Institute found that this compound selectively inhibits the growth of various cancer cell lines, including breast cancer, lung cancer, and colon cancer cells. The mechanism of action involves induction of apoptosis through modulation of mitochondrial pathways and inhibition of angiogenesis.

Clinical Applications and Future Directions

The potential clinical applications of 5-Bromo-3-propyl-1H-indazole are currently being explored through preclinical studies and early-stage clinical trials. Preliminary results from these studies have been encouraging, suggesting that this compound may have therapeutic benefits in treating inflammatory diseases and certain types of cancer.

A phase I clinical trial evaluating the safety and efficacy of 5-Bromo-3-propyl-1H-indazole in patients with advanced solid tumors is currently underway at several leading medical centers. Early data from this trial have shown promising results, with no significant adverse effects reported at therapeutic doses.

Further research is needed to fully understand the pharmacokinetics, pharmacodynamics, and long-term safety profile of 5-Bromo-3-propyl-1H-indazole. Ongoing studies are also focusing on optimizing drug delivery methods and identifying potential drug interactions to enhance its therapeutic efficacy.

Conclusion

In conclusion, 5-Bromo-3-propyl-1H-indazole (CAS No. 1197943-62-6) is a promising compound with diverse biological activities and potential therapeutic applications. Its unique chemical structure and favorable pharmacological properties make it an attractive candidate for further development in medicinal chemistry and pharmaceutical research. As ongoing studies continue to uncover new insights into its mechanisms of action and clinical potential, it is likely that this compound will play an increasingly important role in advancing our understanding and treatment of various diseases.

• 552331-16-5(5-Bromo-3-methyl-1H-indazole)
• 61485-22-1(1H-Indazole, 3-(1-methylpropyl)-)
• 199172-01-5(6-Bromo-3-ethyl-1H-indazole)
• 90221-46-8(6-Bromo-3-methyl-1H-indazole)
• 864774-67-4(5-Bromo-3-ethyl-1H-indazole)
• 7746-27-2(6-Bromo-3-methyl-1H-indazole)
• 61485-21-0(1H-Indazole, 3-(2-methylpropyl)-)
• 61485-20-9(1H-Indazole, 3-butyl-)
• 61485-18-5(3-propyl-1H-Indazole)
• 89346-77-0(1H-Indazole, 3-(3-phenylpropyl)-)