5-(3,5-Difluorobenzyl)-1H-indazol-3-amine
[CAS# 1108745-30-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 5-(3,5-Difluorobenzyl)-1H-indazol-3-amine
• Molecular Formula: C₁₄H₁₁F₂N₃
• Molecular Weight: 259.25
• CAS Registry Number: 1108745-30-7
• EC Number: 834-084-2
• SMILES: C1=CC2=C(C=C1CC3=CC(=CC(=C3)F)F)C(=NN2)N

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.682, Calc.^*
• Boiling Point: 450.7±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 226.4±27.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1A	H317

Discovery and Applications

5-(3,5-Difluorobenzyl)-1H-indazol-3-amine, known in scientific literature as a potent and selective inhibitor of receptor tyrosine kinases (RTKs), was discovered in the early 21st century through extensive pharmaceutical research and development. Researchers aimed to create a compound that could effectively target and inhibit specific RTKs involved in cancer cell proliferation and survival. This discovery was part of broader efforts to develop targeted therapies that offer a more precise treatment option for cancer patients, minimizing damage to normal cells and reducing side effects compared to traditional chemotherapy.

The compound has shown efficacy in preclinical studies against several types of cancers, particularly those driven by abnormal RTK signaling. These include lung cancer, breast cancer, and certain leukemias. By specifically targeting aberrant signaling pathways, the compound offers a promising therapeutic strategy for tumors that are resistant to conventional treatments.

The compound serves as a valuable tool in cancer research, helping scientists understand the role of RTKs in cancer biology. Its selective inhibition of RTKs allows for detailed studies on how these kinases contribute to tumor growth and survival, leading to the identification of new therapeutic targets and the development of more effective cancer treatments.

5-(3,5-Difluorobenzyl)-1H-indazol-3-amine is also being explored in combination with other anticancer agents. Combining this RTK inhibitor with other drugs can enhance therapeutic efficacy, overcome resistance mechanisms, and provide a multi-faceted approach to cancer treatment. For example, it can be paired with immune checkpoint inhibitors to boost the immune system's ability to fight cancer or with chemotherapy agents to improve their effectiveness.

Advances in genetic and molecular profiling of tumors have facilitated the use of 5-(3,5-Difluorobenzyl)-1H-indazol-3-amine in personalized medicine. By identifying patients whose cancers exhibit specific RTK mutations or overexpression, clinicians can tailor treatment plans to achieve the best possible outcomes. This personalized approach ensures that patients receive the most appropriate therapy based on the molecular characteristics of their tumors.

References

2020. Entrectinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-05-0141