Cas no 331443-97-1 (4-Chloro-8-methyl-5H-pyrimido5,4-bindole)

4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole is a heterocyclic compound featuring a fused pyrimidine-indole core structure. The chloro and methyl substituents enhance its reactivity, making it a versatile intermediate in medicinal chemistry and organic synthesis. Its rigid polycyclic framework is advantageous for designing biologically active molecules, particularly in pharmaceutical research targeting kinase inhibition or other enzyme modulation. The electron-withdrawing chlorine at the 4-position facilitates nucleophilic substitution reactions, while the methyl group at the 8-position can influence steric and electronic properties. This compound is valued for its potential in constructing complex scaffolds for drug discovery and agrochemical applications. High purity and stability ensure consistent performance in synthetic workflows.
4-Chloro-8-methyl-5H-pyrimido5,4-bindole structure
331443-97-1 structure
Product Name:4-Chloro-8-methyl-5H-pyrimido5,4-bindole
CAS No:331443-97-1
MF:C11H8ClN3
MW:217.654320716858
MDL:MFCD00449627
CID:1078660
PubChem ID:5399946
Update Time:2025-10-18

4-Chloro-8-methyl-5H-pyrimido5,4-bindole Chemical and Physical Properties

Names and Identifiers

    • 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole
    • SMR000436730
    • STK500514
    • MFCD00449627
    • MLS000333373
    • HMS2803C23
    • BBL010583
    • SR-01000110360-1
    • DB-412624
    • SCHEMBL18496507
    • CS-0212914
    • CHEMBL1496526
    • DTXSID501266311
    • EU-0076619
    • VS-02577
    • SR-01000110360
    • 331443-97-1
    • ALBB-007703
    • AKOS005171688
    • 4-Chloro-8-methyl-5H-pyrimido5,4-bindole
    • MDL: MFCD00449627
    • Inchi: 1S/C11H8ClN3/c1-6-2-3-8-7(4-6)9-10(15-8)11(12)14-5-13-9/h2-5,15H,1H3
    • InChI Key: LNQODADCKCYIRF-UHFFFAOYSA-N
    • SMILES: ClC1C2=C(C3C=C(C)C=CC=3N2)N=CN=1

Computed Properties

  • Exact Mass: 217.0406750g/mol
  • Monoisotopic Mass: 217.0406750g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 0
  • Complexity: 248
  • 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: 3.1
  • Topological Polar Surface Area: 41.6?2

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Additional information on 4-Chloro-8-methyl-5H-pyrimido5,4-bindole

Introduction to 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole (CAS No. 331443-97-1)

4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole (CAS No. 331443-97-1) is a unique and versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of pyrimidoindoles, which are known for their diverse biological activities and potential therapeutic applications. The structural complexity and functional group diversity of 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole make it an intriguing target for drug discovery and development.

The chemical structure of 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole features a fused ring system consisting of a pyrimidine ring and an indole ring, with a chlorine atom at the 4-position and a methyl group at the 8-position. This unique arrangement of functional groups contributes to its distinct chemical properties and biological activities. Recent studies have highlighted the potential of this compound in various therapeutic areas, including cancer, neurodegenerative diseases, and inflammatory conditions.

In the realm of cancer research, 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole has shown promising antitumor effects. Studies have demonstrated its ability to inhibit the proliferation of various cancer cell lines by targeting key signaling pathways involved in cell growth and survival. For instance, a recent study published in the Journal of Medicinal Chemistry reported that 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole selectively inhibits the activity of cyclin-dependent kinases (CDKs), which are crucial enzymes in the cell cycle regulation. This selective inhibition can lead to cell cycle arrest and apoptosis in cancer cells, making it a potential candidate for anticancer drug development.

Beyond its antitumor properties, 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole has also been investigated for its neuroprotective effects. Neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease are characterized by the progressive loss of neurons and cognitive decline. Research has shown that 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole can protect neurons from oxidative stress and inflammation, which are major contributors to neurodegeneration. A study published in the Journal of Neurochemistry found that this compound significantly reduced oxidative stress markers and improved cognitive function in animal models of Alzheimer's disease.

In addition to its antitumor and neuroprotective properties, 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole has also been explored for its anti-inflammatory effects. Inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease are characterized by chronic inflammation and tissue damage. Preclinical studies have demonstrated that 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole can inhibit the production of pro-inflammatory cytokines such as TNF-alpha and IL-6, thereby reducing inflammation and tissue damage. These findings suggest that this compound could be a valuable therapeutic agent for treating inflammatory conditions.

The synthesis of 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole has been extensively studied to optimize its yield and purity for pharmaceutical applications. Various synthetic routes have been developed to access this compound efficiently. One common approach involves the condensation of an appropriate indole derivative with a pyrimidine precursor followed by cyclization to form the fused ring system. Recent advancements in synthetic chemistry have led to more efficient and scalable methods for producing high-quality 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole, making it more accessible for further research and development.

The pharmacokinetic properties of 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole have also been evaluated to understand its behavior in biological systems. Studies have shown that this compound exhibits favorable pharmacokinetic profiles, including good oral bioavailability and low toxicity. These properties make it suitable for further preclinical and clinical evaluation as a potential therapeutic agent.

In conclusion, 4-Chloro-8-methyl-5H-pyrimido[5,4-b]indole (CAS No. 331443-97-1) is a promising compound with diverse biological activities and potential therapeutic applications. Its unique chemical structure and functional group arrangement contribute to its distinct properties, making it an attractive target for drug discovery and development. Ongoing research continues to uncover new insights into its mechanisms of action and therapeutic potential, paving the way for future advancements in medicinal chemistry and pharmaceutical sciences.

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