Cas no 1427504-16-2 (6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde)

6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde is a heterocyclic organic compound featuring a pyrrolopyridine core with a formyl group at the 2-position and a methyl substituent at the 6-position. This structure makes it a versatile intermediate in pharmaceutical and agrochemical synthesis, particularly for the development of biologically active molecules. The aldehyde functionality allows for further derivatization via condensation or nucleophilic addition reactions, while the methyl group enhances stability and modulates electronic properties. Its rigid fused-ring system contributes to selective binding in medicinal chemistry applications. The compound is typically handled under controlled conditions due to its reactivity, and purity is critical for consistent performance in synthetic workflows.
6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde structure
1427504-16-2 structure
Product Name:6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde
CAS No:1427504-16-2
MF:C9H8N2O
MW:160.17262172699
CID:1088817
PubChem ID:71721018
Update Time:2025-10-28

6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde
    • DTXSID90856876
    • 1427504-16-2
    • Inchi: 1S/C9H8N2O/c1-6-2-3-7-4-8(5-12)11-9(7)10-6/h2-5H,1H3,(H,10,11)
    • InChI Key: CABCMFVEFCLZOY-UHFFFAOYSA-N
    • SMILES: O=CC1=CC2=CC=C(C)N=C2N1

Computed Properties

  • Exact Mass: 160.063662883g/mol
  • Monoisotopic Mass: 160.063662883g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 183
  • 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: 1.5
  • Topological Polar Surface Area: 45.8?2

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Additional information on 6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde

Introduction to 6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (CAS No. 1427504-16-2)

6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde, with the chemical formula C11H9NO, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology due to its unique structural properties and potential biological activities. This compound belongs to the pyrrolopyridine class, a scaffold that is widely recognized for its role in the development of various therapeutic agents. The presence of a formyl group at the 2-position and a methyl substituent at the 6-position of the pyrrolopyridine core enhances its reactivity and makes it a valuable intermediate in synthetic chemistry.

The CAS number 1427504-16-2 provides a unique identifier for this compound, ensuring consistency and precision in scientific literature and industrial applications. As research in drug discovery continues to evolve, compounds like 6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde are being explored for their potential in modulating various biological pathways. The pyrrolopyridine scaffold is particularly interesting because it can mimic natural product structures and has been shown to interact with multiple targets in biological systems.

Recent studies have highlighted the importance of 6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde in the development of small-molecule inhibitors. For instance, researchers have demonstrated its utility in designing compounds that target enzymes involved in cancer metabolism. The aldehyde functionality at the 2-position allows for further derivatization, enabling the creation of libraries of compounds with tailored biological activities. This flexibility makes it an attractive building block for high-throughput screening and structure-activity relationship (SAR) studies.

In addition to its role in oncology research, 6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde has shown promise in other therapeutic areas. For example, its structural motif is similar to that of certain neurotransmitter receptor ligands, suggesting potential applications in neuropharmacology. The compound’s ability to cross the blood-brain barrier and interact with central nervous system receptors makes it a candidate for treating neurological disorders. Furthermore, its interaction with metal ions has been investigated, as metalloproteinases play crucial roles in various diseases, including inflammation and neurodegeneration.

The synthesis of 6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde involves multi-step organic transformations that highlight the ingenuity of modern synthetic methods. One common approach involves the condensation of appropriately substituted pyrroles with ketones or aldehydes, followed by functional group modifications to introduce the desired substituents. Advances in catalytic processes have enabled more efficient and scalable syntheses, reducing costs and improving yields. These advancements are critical for translating laboratory discoveries into viable drug candidates.

The pharmacological profile of 6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde is still being elucidated, but preliminary data suggest that it may exhibit inhibitory activity against certain kinases and other enzymes relevant to metabolic diseases. The compound’s ability to modulate enzyme activity could lead to novel therapeutic strategies for conditions such as diabetes and obesity. Additionally, its structural similarity to known bioactive molecules suggests that it may have off-target effects that could be exploited for therapeutic benefit.

In conclusion, 6-Methyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (CAS No. 1427504-16-2) is a versatile heterocyclic compound with significant potential in pharmaceutical research. Its unique structural features and reactivity make it a valuable tool for developing new drugs targeting various diseases. As our understanding of biological systems continues to grow, compounds like this will play an increasingly important role in drug discovery and development. The ongoing exploration of its biological activities and synthetic applications promises to yield exciting advancements in medicine.

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