Cas no 1000340-27-1 (6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid)

6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid is a heterocyclic carboxylic acid derivative with a fused pyrrolopyridine core, serving as a versatile intermediate in pharmaceutical and agrochemical synthesis. Its structural framework is valuable for constructing biologically active compounds, particularly in the development of kinase inhibitors and other therapeutic agents. The methyl substitution at the 6-position enhances stability and modulates electronic properties, while the carboxylic acid group provides a functional handle for further derivatization. This compound exhibits high purity and consistent performance, making it suitable for rigorous research applications. Its well-defined reactivity profile ensures reliable outcomes in coupling reactions, amide formations, and other synthetic transformations.
6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid structure
1000340-27-1 structure
Product Name:6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid
CAS No:1000340-27-1
MF:C9H8N2O2
MW:176.172021865845
MDL:MFCD09880115
CID:840562
PubChem ID:24729554
Update Time:2025-10-29

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

Names and Identifiers

    • 6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid
    • 6-Methyl-7-azaindole-3-carboxylic acid
    • 2-(6-METHYL-1H-PYRROLO[2,3-B]PYRIDIN-3-YL)ACETIC ACID
    • 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 6-methyl-
    • SCHEMBL23749744
    • 1000340-27-1
    • CS-0054381
    • P10828
    • 6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylicacid
    • 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 6-methyl-
    • DTXSID30646874
    • SB14336
    • AKOS006312990
    • MDL: MFCD09880115
    • Inchi: 1S/C9H8N2O2/c1-5-2-3-6-7(9(12)13)4-10-8(6)11-5/h2-4H,1H3,(H,10,11)(H,12,13)
    • InChI Key: QDLZITJKHXRFDU-UHFFFAOYSA-N
    • SMILES: OC(C1=CNC2C1=CC=C(C)N=2)=O

Computed Properties

  • Exact Mass: 176.058577502g/mol
  • Monoisotopic Mass: 176.058577502g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 220
  • 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: 1.2
  • Topological Polar Surface Area: 66?2

Experimental Properties

  • Density: 1.421±0.06 g/cm3 (20 oC 760 Torr),
  • Solubility: Slightly soluble (3 g/l) (25 o C),

6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid Pricemore >>

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

Introduction to 6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (CAS No. 1000340-27-1)

6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, identified by the Chemical Abstracts Service Number (CAS No.) 1000340-27-1, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology due to its unique structural framework and potential biological activities. This compound belongs to the pyrrolopyridine class, which is a privileged scaffold in drug discovery, often exhibiting a wide range of pharmacological properties. The presence of a carboxylic acid functional group at the 3-position and a methyl substituent at the 6-position contributes to its distinct chemical and biological characteristics, making it a valuable intermediate in the synthesis of more complex molecules.

The 6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid scaffold has been extensively studied for its role in modulating various biological pathways. Recent advancements in medicinal chemistry have highlighted its potential as a building block for the development of novel therapeutic agents. For instance, derivatives of this compound have shown promise in inhibiting enzymes involved in inflammatory responses and cancer progression. The pyrrolopyridine core is particularly noted for its ability to interact with biological targets such as kinases and transcription factors, which are critical in maintaining cellular homeostasis.

In the context of drug design, the structural versatility of 6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid allows for modifications at multiple positions, enabling the optimization of pharmacokinetic and pharmacodynamic properties. Researchers have leveraged this flexibility to develop compounds with enhanced binding affinity and reduced toxicity. For example, studies have demonstrated that substituents introduced at the 1-position and 4-position of the pyrrolopyridine ring can significantly alter the compound's interaction with biological receptors, leading to improved therapeutic efficacy.

One of the most compelling aspects of 6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid is its role in the development of small-molecule inhibitors targeting protein-protein interactions (PPIs). PPIs are involved in numerous cellular processes and are often implicated in diseases such as cancer and neurodegenerative disorders. By designing molecules that selectively disrupt these interactions, researchers aim to develop treatments that can modulate disease pathways effectively. The carboxylic acid moiety in this compound provides a suitable site for covalent bonding or hydrogen bonding interactions with PPI targets, enhancing binding specificity.

The synthesis of 6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid involves multi-step organic reactions that require careful optimization to ensure high yield and purity. Common synthetic routes include cyclization reactions followed by functional group transformations such as carboxylation and methylation. Advances in catalytic methods have enabled more efficient and sustainable synthetic strategies, reducing the environmental impact of producing this compound on an industrial scale.

Recent studies have also explored the role of 6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid in modulating central nervous system (CNS) disorders. The pyrrolopyridine scaffold has been found to cross the blood-brain barrier efficiently, making it an attractive candidate for treating neurological conditions such as Alzheimer's disease and Parkinson's disease. Preclinical investigations have shown that certain derivatives of this compound can inhibit amyloid-beta aggregation and tau hyperphosphorylation, key pathological features associated with these neurodegenerative diseases.

The pharmaceutical industry continues to invest heavily in exploring new applications for 6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, recognizing its potential as a versatile scaffold for drug discovery. Collaborative efforts between academic researchers and industry scientists are driving innovation in synthesizing novel derivatives with improved pharmacological profiles. These efforts are supported by computational modeling techniques that predict how different structural modifications will affect biological activity, accelerating the drug development process.

In conclusion,6-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (CAS No. 1000340-27-1) represents a promising area of research in medicinal chemistry. Its unique structural features and potential biological activities make it a valuable tool for developing new therapeutic agents targeting various diseases. As research continues to uncover new applications for this compound, it is expected to play an increasingly important role in pharmaceutical innovation.

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