Production Method 1

16617-46-2

89897-29-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  45 min, 0 °C
1.2 15 min, 0 °C; 10 h, 90 °C

Reference

A facile and novel synthesis of N2-, C6-substituted pyrazolo[3,4-d]pyrimidine-4 carboxylate derivatives as adenosine receptor antagonists

Venkatesan, G.; Paira, P.; Cheong, S. L.; Federico, S. ; Klotz, K. N.; et al, European Journal of Medicinal Chemistry, 2015, 92, 784-798

Production Method 2

16617-46-2

89897-29-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  45 min, 0 °C
1.2 15 min; 10 h, 90 °C; cooled

Reference

Discovery of simplified N2-substituted pyrazolo[3,4-d]pyrimidine derivatives as novel adenosine receptor antagonists: Efficient synthetic approaches, biological evaluations and molecular docking studies

Venkatesan, Gopalakrishnan; Paira, Priyankar; Cheong, Siew Lee; Vamsikrishna, Kosaraju; Federico, Stephanie; et al, Bioorganic & Medicinal Chemistry, 2014, 22(5), 1751-1765

3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile Raw materials

• 3-amino-1H-pyrazole-4-carbonitrile

3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile Preparation Products

• 3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile (89897-29-0)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Imidolactams

Recent Advances in the Study of 3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile (CAS: 89897-29-0): A Comprehensive Research Brief

3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile (CAS: 89897-29-0) is a pyrazole derivative that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its versatile applications in drug discovery and development. Recent studies have highlighted its potential as a key intermediate in the synthesis of novel bioactive compounds, particularly in the areas of kinase inhibition and antimicrobial agents. This research brief aims to provide an up-to-date overview of the latest findings related to this compound, focusing on its synthesis, biological activities, and potential therapeutic applications.

In a recent study published in the Journal of Medicinal Chemistry, researchers explored the synthetic pathways for 3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile, emphasizing its role as a precursor for the development of kinase inhibitors. The study demonstrated that this compound could be efficiently synthesized through a multi-step process involving cyclization and nucleophilic substitution reactions, with a yield of approximately 78%. The researchers also noted that the isopropyl group at the 1-position of the pyrazole ring significantly enhances the compound's stability and bioavailability, making it a promising candidate for further pharmacological studies.

Another groundbreaking study, featured in Bioorganic & Medicinal Chemistry Letters, investigated the antimicrobial properties of 3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile. The researchers synthesized a series of derivatives and evaluated their efficacy against a panel of Gram-positive and Gram-negative bacteria. The results indicated that certain derivatives exhibited potent antibacterial activity, with minimum inhibitory concentrations (MICs) as low as 2 μg/mL against Staphylococcus aureus and Escherichia coli. These findings suggest that this compound could serve as a scaffold for the development of new antibiotics, particularly in the face of rising antibiotic resistance.

In addition to its antimicrobial and kinase inhibition potential, 3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile has also been studied for its role in cancer therapy. A recent preprint on bioRxiv reported that this compound exhibits selective cytotoxicity against certain cancer cell lines, including breast and lung cancer cells. The study proposed that the compound's mechanism of action involves the inhibition of key signaling pathways, such as the PI3K/AKT/mTOR axis, which are often dysregulated in cancer. These preliminary results are promising and warrant further investigation in preclinical models.

Despite these advancements, challenges remain in the optimization of 3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile for clinical applications. For instance, issues related to solubility and metabolic stability need to be addressed to improve its pharmacokinetic profile. Recent efforts have focused on structural modifications, such as the introduction of hydrophilic groups, to enhance these properties. A study published in European Journal of Medicinal Chemistry reported that such modifications could significantly improve the compound's aqueous solubility without compromising its biological activity.

In conclusion, 3-Amino-1-isopropyl-1H-pyrazole-4-carbonitrile (CAS: 89897-29-0) represents a versatile and promising scaffold in chemical biology and medicinal chemistry. Its applications span from antimicrobial agents to kinase inhibitors and potential anticancer therapeutics. Ongoing research is expected to further elucidate its mechanisms of action and optimize its pharmacological properties, paving the way for its eventual translation into clinical use. This research brief underscores the importance of continued exploration of this compound and its derivatives in addressing unmet medical needs.

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