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  • Recent Advances in Pyrazole and Pyrazolo[1,5-a] pyrimidine Derivatives: Synthesis, Biological Activities, and Therapeutic Applications in Cancer and Inflammation

  • Photo Vishakha Daga* Photo Amankumar Kansagara

  • St Xavier's College Ahmedabad.

Abstract

Pyrazole and pyrazolo[1,5-a] pyrimidine derivatives represent a significant class of heterocyclic compounds with remarkable pharmacological properties and therapeutic potential. This comprehensive review examines the recent advances in the synthesis and biological evaluation of these compounds, with particular emphasis on their anticancer and anti-inflammatory activities. The unique structural features of pyrazole rings, consisting of five-membered heterocycles with two adjacent nitrogen atoms, provide a versatile scaffold for drug development. Pyrazolo[1,5-a] pyrimidines, characterized by their fused bicyclic system incorporating both pyrazole and pyrimidine rings, have emerged as potent protein kinase inhibitors with significant applications in targeted cancer therapy. This review covers synthetic methodologies including cyclization approaches, microwave-assisted synthesis, and green chemistry methods, as well as their structure-activity relationships. The biological activities discussed encompass anticancer effects through various mechanisms including protein kinase inhibition, tubulin polymerization inhibition, and DNA interaction, alongside anti-inflammatory properties through inhibition of cyclooxygenase and other inflammatory mediators. Recent developments in dual-targeting approaches and multi-kinase inhibition strategies are also highlighted. The review concludes with future perspectives on optimizing these compounds for enhanced therapeutic efficacy and reduced toxicity.

Keywords

pyrazole derivatives, pyrazolo[1,5-a]pyrimidine, anticancer agents, protein kinase inhibitors, anti-inflammatory, synthesis

Introduction

Cancer and inflammatory disorders remain among the leading causes of morbidity and mortality worldwide (1). The development of targeted therapeutic agents has revolutionized the treatment landscape, with heterocyclic compounds playing a crucial role in modern drug discovery (2). Among these, pyrazole and pyrazolo[1,5-a]pyrimidine derivatives have emerged as particularly promising scaffolds due to their diverse biological activities and structural versatility (3). Pyrazole is a five-membered aromatic heterocyclic compound containing two adjacent nitrogen atoms at positions 1 and 2 (4). The unique chemical structure of pyrazole imparts polarity and reactivity due to the presence of nitrogen atoms, making it amenable to various substitution reactions (5). This structural flexibility provides ample opportunities for designing and developing novel drugs with enhanced selectivity and potency (6). The significance of pyrazole derivatives in medicinal chemistry is exemplified by several clinically approved drugs including celecoxib (COX-2 inhibitor), crizotinib (ALK/ROS1 inhibitor), and rimonabant (CB1 receptor antagonist) (7). These successful examples have validated the pyrazole scaffold as a privileged structure in drug development and have stimulated extensive research into novel pyrazole-based therapeutics (8). Pyrazolo[1,5-a]pyrimidines represent a particularly important subclass, featuring a fused bicyclic system that combines the pharmacologically active pyrazole ring with a six-membered pyrimidine ring (9). This fused structure offers enhanced rigidity and planarity, often resulting in improved binding affinity to biological targets, particularly protein kinases (10). The structural diversity possible through substitution at various positions on both rings has enabled the development of highly selective and potent inhibitors for numerous therapeutic targets (11).

2. Synthetic Strategies for Pyrazole and Pyrazolo[1,5-a] pyrimidine Derivatives

2.1 Classical Synthesis Methods

The synthesis of pyrazole derivatives has been extensively studied, with several well-established methodologies available (12). The classical Knorr synthesis remains one of the most widely used approaches, involving the condensation of β-diketones with hydrazine derivatives under acidic conditions (13). This method typically proceeds through the formation of a hydrazone intermediate followed by cyclization to yield the desired pyrazole ring (14).  El-Enany et al. demonstrated the synthesis of novel pyrazolo[1,5-a]pyrimidine derivatives through a multi-step approach starting from 5-amino-3-methylsulfanyl-1H-pyrazole-4-carbonitrile (15). The key intermediate was prepared by reacting substituted benzylidenemalononitriles with the aminopyrazole precursor under basic conditions, resulting in both dihydro and aromatic pyrazolo[1,5-a]pyrimidine derivatives with good yields (15).

2.2 Cyclization Approaches

Figure 1: Knorr synthesis. This will visually demonstrate the hydrazone intermediate formation and cyclization mechanism.

Modern synthetic strategies have focused on developing efficient cyclization methods for constructing the pyrazolo[1,5-a]pyrimidine core (16). Sikdar et al. reported an innovative one-pot cyclization methodology for synthesizing 3-halo-pyrazolo[1,5-a]pyrimidine derivatives through reactions involving amino pyrazoles, enaminones, and sodium halides (17). This approach utilized potassium persulfate as an oxidizing agent and demonstrated excellent functional group tolerance with yields approaching quantitative levels (17).

Figure 2: Synthesis of Pyrazolo[1,5-a] pyrimidine Compounds

Reagents and conditions: (a) N, N-dimethylformamide dimethyl acetal, reflux, 4 h, 50%; (b) N2H4, HOAc, ethanol, reflux, 16 h, 97%; (c) N-methyl uracil, C2H5ONa, ethanol, reflux, 3 h, 62%; (d) POCl3, reflux, 3 h, 67%; (e) DIPEA, iPrOH, 130 °C, microwave irradiation, 16 h, 80%.

Figure 3: Strategies Toward the Synthesis of Halogenated Pyrazolo[1,5-a] pyrimidines

The cyclization strategy offers significant advantages including operational simplicity, high atom economy, and the ability to introduce various substituents at specific positions (18). Portilla et al. explored the reaction of 3-substituted-5-amino-1H-pyrazoles with cyclic β-dicarbonyl compounds, achieving regioselective formation of cyclopentapyrazolo[1,5-a]pyrimidines under both conventional heating and microwave irradiation conditions (19).

2.3 Microwave-Assisted Synthesis

Microwave-assisted synthesis has emerged as a powerful tool for the efficient preparation of pyrazole and pyrazolo[1,5-a]pyrimidine derivatives (20). Castillo et al. developed a microwave-assisted approach for the regioselective synthesis of functionalized 6-(aryldiazenyl)pyrazolo[1,5-a]pyrimidin-7-amines under solvent-free conditions (21). This method achieved near-quantitative yields in reaction times as short as four minutes, demonstrating the efficiency of microwave activation (21).

Figure 4: Synthesis of benzimidazole derivatives. Reagents and conditions:

(i) CaCl2, NaBH4, EtOH, reflux, 3 h, 99%; (ii) Dess–Martin periodinane, DMF, RT, 2 h, 46%; (iii) 1-tert-butylipiperazine, sodium triacetoxyborohydride, DCM, RT, 18 h, 84%; (iv) benzimidazole derivative, tris(dibenzylideneacetone)dipalladium(0), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, Cs2CO3, toluene, 150 °C, 6 h, 200 W, MW, 4–93%; (v) 2-(4-piperidyl)-2-propanol, sodium triacetoxyborohydride, DCM, RT, 63%; (vi) benzimidazole derivative, tris(dibenzylideneacetone)dipalladium(0), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene, Cs2CO3, toluene, 150 °C, 6 h, 200 W, MW, 52–66%.

The advantages of microwave-assisted synthesis include reduced reaction times, improved yields, enhanced selectivity, and environmental benefits due to reduced solvent usage (22). Recent bibliometric analysis indicates that microwave irradiation was employed in 68% of studies on pyrazole derivative synthesis published between 2014 and 2024 (23).

2.4 Green Chemistry Approaches

Environmental considerations have driven the development of green synthesis methods for pyrazole derivatives (24). The use of heterogeneous catalysts, solvent-free conditions, and alternative energy sources such as ultrasound and mechanochemistry have gained prominence (25). Khatab et al. demonstrated the synthesis of 5-aminopyrazole derivatives using V?O?/SiO? as a heterogeneous catalyst under solvent-free conditions, achieving excellent yields (88-95%) with improved environmental sustainability (26).

3. Biological Activities and Therapeutic Applications

3.1 Anticancer Activity

3.1.1 Protein Kinase Inhibition

Protein kinases represent one of the most important classes of therapeutic targets in cancer therapy (27). Pyrazolo[1,5-a]pyrimidines have demonstrated exceptional potential as protein kinase inhibitors, with activities against various kinases including EGFR, BRAF, CDK, and MEK (28). Iorkula et al. provided a comprehensive review of pyrazolo[1,5-a]pyrimidines as protein kinase inhibitors, highlighting their role in targeted cancer therapy (29). Recent studies by Abdel-Maksoud et al. described the design and synthesis of novel pyrimidine-pyrazole hybrids with dual anticancer and anti-inflammatory effects targeting BRAFV600E and JNK kinases (30). Compound 14c from this series showed the highest activity on JNK isoforms and BRAFV600E with IC?? values of  0.51 μM, 0.53 μM, 1.03 μM, and 0.009 μM for JNK1, JNK2, JNK3, and BRAFV600E, respectively (30).

Figure 5: Docking pose and putative binding interactions of compound 46 with JNK-1 kinase crystal structure (69).

3.1.2 Tubulin Polymerization Inhibition

Several pyrazole derivatives have demonstrated potent tubulin polymerization inhibitory activity (31). Zhang et al. reported that pyrazole derivatives can interact with tubulin through binding to the colchicine site, leading to disruption of microtubule dynamics and subsequent cell cycle arrest (32). This mechanism has proven particularly effective against various cancer cell lines, with some compounds showing IC?? values in the nanomolar range (32).

3.1.3 DNA Interaction         

DNA binding represents another important mechanism of anticancer activity for pyrazole derivatives (33). Omran et al. synthesized polysubstituted pyrazole derivatives that demonstrated superior DNA binding affinity, displacing 90.14% of methyl green in competitive binding assays (34). Molecular docking studies revealed that these compounds preferentially bind to the minor groove of DNA (34).

3.2 Anti-inflammatory Activity

The anti-inflammatory properties of pyrazole derivatives have been extensively documented (35). The most well-known example is celecoxib, a selective COX-2 inhibitor used for treating inflammatory conditions (36). Recent research has focused on developing dual COX/LOX inhibitors and novel anti-inflammatory mechanisms (37).

Compounds from the study by Abdel-Maksoud et al. showed significant ability to inhibit nitric oxide release and prostaglandin E2 (PGE2) production in RAW 264.7 macrophages (30). The most potent compounds demonstrated over 90% inhibition at 10 μM concentrations and exhibited high inhibitory effects on inducible nitric oxide synthase (iNOS) and COX-2 compared to COX-1 (30).

3.3 Antimicrobial Activity

Recent studies have highlighted the antimicrobial potential of pyrazole derivatives (38). Al-Mohammadi et al. synthesized novel peptides containing modified pyrazolopyrimidine moieties and evaluated their antibacterial activity against selected bacterial strains (39). The peptide-conjugated pyrazolopyrimidines showed superior activity compared to the parent pyrazolopyrimidine compounds alone, with compounds 15 and 17 effectively inhibiting Pseudomonas aeruginosa growth at MIC ≥ 1 μg/mL (39). The antimicrobial activity of pyrazole derivatives has been attributed to their ability to disrupt bacterial cell membranes and interfere with essential cellular processes (40). Ultra-short pyrazole-arginine based antimicrobial peptidomimetics have shown particular promise against antibiotic-resistant bacteria, including MRSA, MDRPA, and VREF (41).

4. Structure-Activity Relationships

Understanding the structure-activity relationships (SAR) of pyrazole and pyrazolo[1,5-a]pyrimidine derivatives is crucial for rational drug design (42). Several key structural features have been identified as important for biological activity:

4.1 Substitution Patterns

The position and nature of substituents on the pyrazole ring significantly influence biological activity (43). Electron-withdrawing groups at specific positions often enhance kinase inhibitory activity, while hydrophobic substituents can improve membrane permeability and cellular uptake (44). In the study by Abdel-Maksoud et al., compounds with electron-withdrawing groups (Br, Cl, F) showed higher activity against JNK isoforms and BRAFV600E compared to those with electron-donating groups (30).

4.2 Ring Fusion Effects

The fusion of pyrazole with pyrimidine rings creates a rigid, planar framework that enhances binding affinity to protein targets (45). The bicyclic structure provides additional hydrogen bonding opportunities and π-π stacking interactions, often resulting in improved selectivity and potency (46).

4.3 Linker Design

In hybrid molecules, the nature of the linker connecting different pharmacophores plays a crucial role in determining biological activity (47). Flexible linkers may allow optimal positioning of pharmacophores in the binding site, while rigid linkers can provide enhanced selectivity through geometric constraints (48).

5. Recent Advances and Emerging Trends

5.1 Dual-Target Inhibitors

The development of compounds targeting multiple therapeutic targets simultaneously has gained significant attention (49). This approach can potentially overcome drug resistance mechanisms and provide enhanced therapeutic efficacy (50). The pyrimidine-pyrazole hybrids described by Abdel-Maksoud et al. exemplify this strategy, showing dual inhibition of BRAFV600E and JNK kinases with promising anticancer and anti-inflammatory effects (30).

5.2 Fused Pyrazole Systems

Recent research has explored various fused pyrazole systems beyond the traditional pyrazolo[1,5-a]pyrimidine core (51). Odeh et al. provided a comprehensive review of bioactive fused pyrazoles inspired by 5-aminopyrazole derivatives, highlighting their potential as antioxidants, anticancer agents, enzyme inhibitors, and antimicrobials (52).

5.3 Peptidomimetic Approaches

The combination of pyrazole scaffolds with peptide sequences represents an innovative approach to drug development (53). Al-Mohammadi et al. demonstrated that peptide conjugation can significantly enhance the antimicrobial activity of pyrazolopyrimidine derivatives (39). This approach offers the potential for improved selectivity and reduced toxicity compared to traditional small-molecule approaches (54).

5.4 Green Synthesis Methods

Environmental sustainability has become increasingly important in pharmaceutical development (55). Recent advances in green synthesis methods for pyrazole derivatives include the use of microwave irradiation, ultrasound-assisted synthesis, and mechanochemical approaches (56). These methods offer advantages such as reduced reaction times, improved yields, and decreased environmental impact (57).

6. Clinical Perspectives and Therapeutic Potential

6.1 Current Clinical Applications

Several pyrazole-containing drugs are currently in clinical use or under development (58). Beyond the established examples like celecoxib and crizotinib, newer compounds are progressing through clinical trials for various therapeutic indications (59). The success of existing pyrazole-based drugs validates the continued exploration of this chemical space for novel therapeutics (60).

6.2 Challenges and Limitations

Despite the promising therapeutic potential, several challenges remain in the development of pyrazole-based drugs (61). These include issues related to selectivity, toxicity, drug resistance, and pharmacokinetic properties (62). Addressing these challenges requires continued research into structure-activity relationships and the development of more sophisticated design strategies (63).

6.3 Future Directions

Future research in pyrazole derivative development should focus on several key areas (64):

  1. Enhanced Selectivity: Development of more selective compounds to reduce off-target effects and improve therapeutic indices (65).
  2. Combination Therapies: Exploration of pyrazole derivatives in combination with existing therapies to overcome resistance mechanisms (66).
  3. Personalized Medicine: Development of biomarkers to identify patients most likely to benefit from specific pyrazole-based therapies (67).
  4. Novel Targets: Identification and validation of new therapeutic targets that can be effectively modulated by pyrazole derivatives (68).

7. CONCLUSION

Pyrazole and pyrazolo[1,5-a]pyrimidine derivatives continue to represent a highly promising class of compounds for drug development. Their structural versatility, combined with demonstrated biological activities across multiple therapeutic areas, makes them attractive scaffolds for medicinal chemists. The recent advances in synthetic methodologies, particularly green chemistry approaches and microwave-assisted synthesis, have improved the accessibility of these compounds for research and development. The biological activities of pyrazole derivatives, particularly their anticancer and anti-inflammatory properties, have been extensively validated through numerous studies. The development of dual-target inhibitors and peptidomimetic approaches represents exciting new directions that may lead to more effective and safer therapeutic agents. While challenges remain, particularly in terms of selectivity and resistance mechanisms, the continued evolution of structure-activity relationship understanding and the development of more sophisticated design strategies provide a strong foundation for future success. The integration of computational approaches, green synthesis methods, and innovative targeting strategies positions pyrazole derivatives as key players in the next generation of therapeutic agents. As the field continues to advance, it is likely that we will see an increasing number of pyrazole-based drugs reaching clinical application, providing new treatment options for patients suffering from cancer, inflammatory diseases, and infectious conditions. The foundation laid by current research provides a robust platform for these future developments.

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Vishakha Daga
Corresponding author

St Xavier's College Ahmedabad.

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Amankumar Kansagara
Co-author

St Xavier's College Ahmedabad.

Vishakha Daga*, Amankumar Kansagara, Recent Advances in Pyrazole and Pyrazolo[1,5-a] pyrimidine Derivatives: Synthesis, Biological Activities, and Therapeutic Applications in Cancer and Inflammation, Int. J. of Pharm. Sci., 2025, Vol 3, Issue 9, 432-443 https://doi.org/10.5281/zenodo.17051742

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