Cas no 1011711-52-6 (3-Acetyl-4-chloro-7-azaindole)

3-Acetyl-4-chloro-7-azaindole is a heterocyclic compound featuring a fused pyrrole-pyridine (azaindole) core, functionalized with acetyl and chloro substituents. This structure imparts versatility as a key intermediate in pharmaceutical and agrochemical synthesis, particularly in the development of kinase inhibitors and other biologically active molecules. The presence of the chloro group enhances reactivity for further functionalization, while the acetyl moiety offers a handle for derivatization. Its rigid azaindole scaffold contributes to improved binding affinity in target interactions. The compound is characterized by high purity and stability, making it suitable for research applications requiring precise molecular modifications.
3-Acetyl-4-chloro-7-azaindole structure
3-Acetyl-4-chloro-7-azaindole structure
Product Name:3-Acetyl-4-chloro-7-azaindole
CAS No:1011711-52-6
MF:C9H7ClN2O
MW:194.61768078804
MDL:MFCD12828645
CID:833059
PubChem ID:24801188
Update Time:2025-05-20

3-Acetyl-4-chloro-7-azaindole Chemical and Physical Properties

Names and Identifiers

    • 1-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone
    • 1H-Pyrazole-1-acetic acid, 5-[4-(4-dibenzofuranyl)phenyl]-4,5-dihydro-3-(4-methoxyphenyl)-
    • 3-Acetyl-4-chloro-7-azaindole
    • 3-acetyl-4-chloro-1H-pyrrolo[2,3-b]pyridine
    • Ethanone,1-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-
    • KB-76849
    • PB34735
    • SureCN1839435
    • 1-(4-CHLORO-1H-PYRROLO[2,3-B]PYRIDIN-3-YL)-ETHANONE
    • 1-{4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethan-1-one
    • ETHANONE, 1-(4-CHLORO-1H-PYRROLO[2,3-B]PYRIDIN-3-YL)-
    • 3-acetyl-4-chloro-7-azaindol
    • UKCGIOZOYKFSGN-UHFFFAOYSA-N
    • 1-{4-CHLORO-1H-PYRROLO[2,3-B]PYRIDIN-3-YL}ETHANONE
    • SY097320
    • AS-50933
    • CS-0004585
    • 1011711-52-6
    • AKOS017514866
    • GEO-03521
    • MFCD12828645
    • P11504
    • SCHEMBL1839435
    • MDL: MFCD12828645
    • Inchi: 1S/C9H7ClN2O/c1-5(13)6-4-12-9-8(6)7(10)2-3-11-9/h2-4H,1H3,(H,11,12)
    • InChI Key: UKCGIOZOYKFSGN-UHFFFAOYSA-N
    • SMILES: ClC1C=CN=C2C=1C(C(C)=O)=CN2

Computed Properties

  • Exact Mass: 194.0246905g/mol
  • Monoisotopic Mass: 194.0246905g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 222
  • 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
  • Topological Polar Surface Area: 45.8
  • XLogP3: 1.6

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Additional information on 3-Acetyl-4-chloro-7-azaindole

Recent Advances in the Study of 3-Acetyl-4-chloro-7-azaindole (CAS: 1011711-52-6) in Chemical Biology and Pharmaceutical Research

3-Acetyl-4-chloro-7-azaindole (CAS: 1011711-52-6) has emerged as a compound of significant interest in chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. Recent studies have focused on its role as a versatile scaffold in drug discovery, particularly in the development of kinase inhibitors and other targeted therapies. This research brief synthesizes the latest findings on this compound, highlighting its chemical characteristics, biological activities, and potential applications in medicine.

The compound's structure, featuring a 7-azaindole core with acetyl and chloro substituents, provides a promising platform for the design of small-molecule inhibitors. Recent publications in journals such as the Journal of Medicinal Chemistry and Bioorganic & Medicinal Chemistry Letters have explored its interactions with various kinase targets, including JAK2 and CDK2. These studies employ a combination of X-ray crystallography, molecular docking, and biochemical assays to elucidate the binding modes and inhibitory mechanisms of 3-Acetyl-4-chloro-7-azaindole derivatives.

One notable study demonstrated the compound's efficacy in modulating JAK-STAT signaling pathways, suggesting potential applications in inflammatory diseases and certain cancers. The research team synthesized a series of analogs and evaluated their potency using cell-based assays and in vivo models. Their findings indicate that specific modifications to the 3-acetyl group can significantly enhance selectivity and reduce off-target effects, paving the way for more targeted therapeutic approaches.

In addition to its kinase inhibitory properties, recent investigations have explored the compound's potential as a building block for fluorescent probes and imaging agents. The 7-azaindole scaffold's inherent fluorescence properties, combined with the chloro substituent's electron-withdrawing effects, make it particularly suitable for developing novel diagnostic tools. A 2023 study published in Chemical Communications detailed the synthesis of a 3-Acetyl-4-chloro-7-azaindole-based probe for detecting reactive oxygen species in live cells, demonstrating its utility in studying oxidative stress-related pathologies.

The synthetic accessibility of 3-Acetyl-4-chloro-7-azaindole has also been a focus of recent research, with several groups reporting improved synthetic routes that enhance yield and purity. A particularly innovative approach published in Organic Process Research & Development describes a continuous flow synthesis method that reduces reaction times and improves scalability, addressing one of the key challenges in translating this compound from bench to bedside.

Looking forward, researchers are exploring the compound's potential in combination therapies and as part of PROTAC (proteolysis targeting chimera) systems. Preliminary data suggest that when conjugated with appropriate E3 ligase ligands, 3-Acetyl-4-chloro-7-azaindole derivatives can effectively target specific proteins for degradation, opening new avenues for drug development in challenging therapeutic areas such as neurodegenerative diseases and resistant cancers.

In conclusion, the growing body of research on 3-Acetyl-4-chloro-7-azaindole (CAS: 1011711-52-6) underscores its importance as a multifunctional scaffold in modern drug discovery. Its applications span from kinase inhibition to molecular imaging, with ongoing studies continuing to reveal new therapeutic possibilities. As synthetic methodologies improve and our understanding of its structure-activity relationships deepens, this compound is poised to play an increasingly significant role in the development of next-generation pharmaceuticals.

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