Cas no 230305-81-4 (3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine)

3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine is a heterocyclic compound featuring a pyrazolo[4,3-c]pyridine core substituted with a trifluoromethyl group at the 3-position. This structure imparts unique electronic and steric properties, making it a valuable intermediate in pharmaceutical and agrochemical research. The trifluoromethyl group enhances lipophilicity and metabolic stability, while the fused pyrazole-pyridine scaffold offers versatile reactivity for further functionalization. Its rigid aromatic system is advantageous in designing bioactive molecules, particularly for targeting kinases and other enzyme classes. The compound’s high purity and well-defined synthetic route ensure reproducibility in research applications. Its utility in medicinal chemistry stems from its ability to modulate physicochemical and pharmacokinetic properties of lead compounds.
3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine structure
230305-81-4 structure
Product Name:3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine
CAS No:230305-81-4
MF:C7H4F3N3
MW:187.121971130371
MDL:MFCD09863958
CID:2836876
PubChem ID:10655176
Update Time:2025-05-26

3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine Chemical and Physical Properties

Names and Identifiers

    • 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine
    • DTXSID10443020
    • Z1198235069
    • 3-Trifluoromethyl-5-aza-1H-indazole
    • 230305-81-4
    • SCHEMBL3452165
    • BS-51145
    • MFCD09863958
    • EN300-109576
    • F2113-0174
    • SY139402
    • SB13724
    • F70994
    • A934501
    • AKOS005208561
    • 879-611-7
    • 3-(trifluoromethyl)-1H-pyrazolo(4,3-c)pyridine
    • FJA30581
    • DTXCID80393841
    • MDL: MFCD09863958
    • Inchi: 1S/C7H4F3N3/c8-7(9,10)6-4-3-11-2-1-5(4)12-13-6/h1-3H,(H,12,13)
    • InChI Key: QVHPHQMHLWQWFX-UHFFFAOYSA-N
    • SMILES: FC(C1=C2C=NC=CC2=NN1)(F)F

Computed Properties

  • Exact Mass: 187.03573163g/mol
  • Monoisotopic Mass: 187.03573163g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 194
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.4
  • Topological Polar Surface Area: 41.6?2

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Additional information on 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine

Introduction to 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine (CAS No: 230305-81-4)

3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry due to its unique structural properties and potential biological activities. The compound belongs to the class of pyrazolopyridine derivatives, which are known for their broad spectrum of pharmacological effects. The presence of a trifluoromethyl group in the molecule enhances its metabolic stability and binding affinity, making it a valuable scaffold for drug discovery.

The chemical structure of 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine consists of a fused ring system comprising a pyrazole ring and a pyridine ring, with the trifluoromethyl substituent attached to the pyrazole ring. This arrangement contributes to the compound's ability to interact with various biological targets, including enzymes and receptors. The trifluoromethyl group, in particular, is known to modulate the electronic properties of the molecule, influencing its reactivity and biological activity.

In recent years, there has been a growing interest in pyrazolopyridine derivatives as potential therapeutic agents. These compounds have shown promise in various preclinical studies, particularly in the treatment of inflammatory diseases, cancer, and neurological disorders. The structural features of 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine make it an attractive candidate for further investigation into its pharmacological properties.

One of the most compelling aspects of 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine is its potential as an intermediate in the synthesis of more complex pharmaceutical molecules. The pyrazolopyridine core can be modified in various ways to create derivatives with enhanced biological activity or improved pharmacokinetic profiles. Researchers have been exploring different synthetic pathways to functionalize this scaffold, leading to a diverse library of compounds that could serve as lead candidates for drug development.

The trifluoromethyl group is particularly noteworthy in this context. It is a common pharmacophore that enhances the binding affinity of small molecules to their targets. This group can also influence the metabolic stability of a compound, reducing the likelihood of rapid degradation in vivo. These properties make 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine a valuable building block for medicinal chemists seeking to develop novel therapeutics.

Recent studies have highlighted the potential of 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine in addressing unmet medical needs. For instance, researchers have investigated its activity against certain kinases involved in cancer progression. The compound has been shown to inhibit the activity of these enzymes, potentially leading to therapeutic benefits. Additionally, its ability to modulate inflammatory pathways has been explored in models of autoimmune diseases.

The synthesis of 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine involves multi-step organic reactions that require careful optimization to ensure high yield and purity. Common synthetic routes include condensation reactions between hydrazines and ketones or aldehydes, followed by functionalization with fluorinated intermediates. Advances in synthetic methodologies have enabled more efficient and scalable production processes for this compound.

The pharmacological evaluation of 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine has revealed several interesting properties. In vitro studies have demonstrated its ability to interact with various biological targets, including protein kinases and transcription factors. These interactions suggest potential therapeutic applications across multiple disease areas. Further preclinical studies are needed to fully characterize its safety profile and efficacy.

One area of active research is the development of trifluoromethylated heterocycles as antiviral agents. The unique electronic properties of trifluoromethylation can enhance the binding affinity of small molecules to viral enzymes or receptors. Preliminary data suggest that 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine may have inhibitory effects against certain viruses, making it a promising candidate for antiviral drug development.

The future prospects for 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine are bright, with ongoing research aimed at expanding its therapeutic applications. Collaborative efforts between academic institutions and pharmaceutical companies are likely to drive innovation in this field. As our understanding of molecular interactions continues to grow, compounds like 3-(Trifluoromethyl)-1H-pyrazolo[4,3-c]pyridine will play an increasingly important role in the development of novel treatments for human diseases.

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