5-[(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid
[CAS# 2434843-97-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 5-[(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid
• Synonyms: 5-[(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid
• Molecular Formula: C₁₂H₁₂N₄O₃
• Molecular Weight: 260.25
• CAS Registry Number: 2434843-97-5
• SMILES: C1[C@@H]2CN([C@H]1CO2)C3=NC4=C(C=NN4C=C3)C(=O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338-P302+P352

Discovory and Applicatios

5-[(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid is a bicyclic heterocyclic compound incorporating a fused tricyclic core and a rigid oxazabicyclo framework. This compound features a pyrazolo[1,5-a]pyrimidine moiety, a structure commonly studied in medicinal chemistry due to its bioactive potential across a range of pharmacological targets, including kinases and nucleic acid-binding enzymes. The additional functionalization at the 5-position with a 2-oxa-5-azabicyclo[2.2.1]heptane substituent, especially in a stereochemically defined (1R,4R) configuration, adds structural complexity and may enhance binding affinity or selectivity to specific biomolecular targets.

This molecule is representative of a broader class of pyrazolopyrimidines, which have been extensively investigated for their role in modulating intracellular signaling pathways. The carboxylic acid group at the 3-position further provides an anchoring point for potential conjugation or interaction with basic residues in active sites of target proteins, increasing the molecule’s pharmacodynamic versatility. Carboxyl groups also influence the solubility and membrane permeability of drug candidates, which is an essential factor in the early stages of lead optimization.

The fused heterocyclic backbone of the pyrazolo\[1,5-a]pyrimidine system allows it to mimic the purine ring found in nucleotides, potentially enabling the compound to interfere with enzymatic processes such as those catalyzed by kinases or phosphodiesterases. The substitution at the 5-position with a bridged bicyclic moiety introduces a degree of conformational rigidity that can be beneficial in drug design, as it limits the degrees of freedom and may improve receptor binding by maintaining a bioactive conformation.

In drug discovery, rigidified analogs like this one are often pursued to improve potency and pharmacokinetic properties. The presence of a 2-oxa-5-azabicyclo[2.2.1]heptane ring also suggests a degree of polarity and potential for hydrogen bonding, which can contribute to specific target engagement. The stereochemistry of the ring, with (1R,4R) configuration, may be critical for optimal activity, as stereoisomers frequently exhibit different biological properties, including efficacy and toxicity profiles.

Though this compound may not be currently approved for therapeutic use, its architecture suggests potential as a lead scaffold in the development of enzyme inhibitors or receptor modulators. The pyrazolopyrimidine core has been incorporated into a number of clinical candidates targeting cancer, inflammation, and autoimmune diseases, owing to its ability to bind ATP-binding pockets or other nucleoside recognition domains.

Given the structural features and functional groups, analogs of 5-[(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid could be evaluated for activity across a panel of biologically relevant assays, particularly those involving protein kinases, GPCRs, or nucleotide-processing enzymes. Further optimization could involve modifications to the carboxylic acid for improved pharmacokinetics or alteration of the oxazabicyclo substituent to tune the compound’s physicochemical properties.