Hangzhou Leap Chem Co., Ltd. is one of the most professional manufacturers and suppliers of 5-azaindole丨cas 271-34-1 in China. Welcome to wholesale custom made chemical products at competitive price from our factory. For more cheap products, contact us now.
Specifications
| Appearance: | Off-white solid |
| Assay: | 98% min |
| Moisture: | 0.2% max |
Applications
1. Medicinal Chemistry
5-Azaindole is widely used as a privileged scaffold in drug discovery due to its bioisosterism with indole and pyridine. It plays a crucial role in:
Kinase inhibitors: Acts as a hinge-binding motif in ATP-competitive inhibitors for kinases like JAK, BTK, and BRAF.
Anticancer agents: Incorporated into molecules targeting oncogenic proteins.
Antiviral drugs: Used in compounds aimed at inhibiting viral replication pathways.
Anti-inflammatory agents: Found in candidate drugs that modulate immune pathways.
Examples:
Found in JAK inhibitors (e.g., filgotinib analogs)
Core structure in some tyrosine kinase inhibitors and CDK inhibitors
2. Fragment-Based Drug Design (FBDD)
Due to its small size, planarity, and favorable hydrogen bonding properties, 5-azaindole is a key fragment in FBDD, helping chemists build more complex and selective bioactive molecules.
3. Heterocyclic Building Block
Used as a starting material or intermediate in the synthesis of:
Complex heterocyclic drug candidates
Bioactive agrochemicals
Functionalized materials for organic electronics
4. Fluorescent Probes & Ligands
Due to its aromatic nature and electron-donating nitrogen atoms, derivatives of 5-azaindole are explored in:
Fluorescent sensors
Molecular recognition studies
Metal chelation and coordination chemistry
Benefits
✅ Bioisosteric Versatility
Serves as a bioisostere for indole and purine moieties, enabling fine-tuning of pharmacokinetic and pharmacodynamic profiles.
Modifies H-bond donor/acceptor patterns to improve drug-receptor binding.
✅ Improved Solubility and Metabolic Stability
Compared to indole, 5-azaindole often imparts better aqueous solubility and metabolic resistance to drug candidates.
✅ Synthetic Accessibility
Readily available commercially and amenable to diverse functionalizations (e.g., halogenation, alkylation, amination), supporting rapid analog generation.
✅ Fragment Efficiency
High ligand efficiency and favorable molecular properties (low MW, high polar surface area) make it ideal in early-stage drug design.
✅ Enhanced Binding Interactions
The additional nitrogen improves π-stacking, hydrogen bonding, and metal coordination capabilities - all key in targeting biological macromolecules.
Conclusion
5-Azaindole (CAS 271-34-1) is a versatile and high-value heterocyclic compound, especially prized in medicinal chemistry for its role in the design of kinase inhibitors, anticancer agents, and other targeted therapies. Its favorable physicochemical properties and synthetic flexibility make it a go-to building block in modern pharmaceutical and chemical research. As drug discovery continues to favor fragment-based and rational design approaches, 5-azaindole's importance is only expected to grow.
