5-((S)-2,2-dimethyltetrahydro-2H-pyran-4-yl)-1-((1S,2S)-2-methyl-1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)cyclopropyl)-1H-indole-2-carboxylic acid
[CAS# 2212021-83-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 5-((S)-2,2-dimethyltetrahydro-2H-pyran-4-yl)-1-((1S,2S)-2-methyl-1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)cyclopropyl)-1H-indole-2-carboxylic acid
• Synonyms: 5-[(4S)-2,2-dimethyloxan-4-yl]-1-[(1S,2S)-2-methyl-1-(5-oxo-4H-1,2,4-oxadiazol-3-yl)cyclopropyl]indole-2-carboxylic acid
• Molecular Formula: C₂₂H₂₅N₃O₅
• Molecular Weight: 411.45
• CAS Registry Number: 2212021-83-3
• SMILES: C[C@H]1C[C@]1(C2=NOC(=O)N2)N3C4=C(C=C(C=C4)[C@H]5CCOC(C5)(C)C)C=C3C(=O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

5-((S)-2,2-dimethyltetrahydro-2H-pyran-4-yl)-1-((1S,2S)-2-methyl-1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)cyclopropyl)-1H-indole-2-carboxylic acid is a synthetic compound known for its structural complexity and potential pharmaceutical relevance. This molecule consists of multiple functional groups, including a substituted indole core, a cyclopropyl group, an oxadiazole ring, and a tetrahydropyran moiety. Each of these structural features contributes to its unique chemical and biological properties, making it a valuable candidate for various therapeutic applications.

The discovery of this compound is rooted in research focusing on indole derivatives, which have long been recognized for their biological activities. The indole scaffold is prevalent in many natural products and pharmaceuticals, making it an attractive framework for drug design. Researchers identified that functionalizing the indole ring with cyclopropyl and oxadiazole groups could enhance the molecule's bioactivity, stability, and binding affinity to biological targets. The inclusion of a tetrahydropyran moiety further improves solubility and pharmacokinetic properties, which are critical for drug development.

The synthesis of 5-((S)-2,2-dimethyltetrahydro-2H-pyran-4-yl)-1-((1S,2S)-2-methyl-1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)cyclopropyl)-1H-indole-2-carboxylic acid typically involves a multi-step process. Key steps include the preparation of the cyclopropyl-oxadiazole intermediate and the subsequent coupling with the indole core. The stereochemistry is controlled through the use of chiral catalysts or auxiliaries, ensuring the correct spatial arrangement of the functional groups. Protecting groups are often employed to facilitate the selective formation of bonds and to prevent side reactions during the synthesis.

This compound has potential applications in the field of medicinal chemistry, particularly as an anti-inflammatory or anti-cancer agent. Indole derivatives have been shown to interact with various enzymes and receptors involved in disease pathways. The presence of the cyclopropyl and oxadiazole groups can enhance binding to target proteins and improve metabolic stability. Additionally, the tetrahydropyran group contributes to the compound's overall pharmacological profile, making it suitable for further development and optimization in drug discovery programs.

Current research efforts aim to explore the full therapeutic potential of this compound. Studies are being conducted to evaluate its efficacy, safety, and mechanism of action. The development of such complex molecules highlights the advances in synthetic organic chemistry and the ongoing quest for new therapeutic agents. This compound's structural features and potential applications underscore its significance in the field of pharmaceutical research.

References

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