Cas no 2433-68-3 (3-ethyl-5-methoxy-1H-indole)

3-Ethyl-5-methoxy-1H-indole is a substituted indole derivative characterized by an ethyl group at the 3-position and a methoxy group at the 5-position of the indole ring. This compound serves as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and bioactive molecules. Its structural features, including the electron-donating methoxy group and the ethyl substituent, enhance its reactivity in electrophilic substitution and cross-coupling reactions. The compound’s stability and well-defined molecular structure make it suitable for precise modifications in medicinal chemistry research. It is commonly employed in the synthesis of serotonin analogs and other heterocyclic compounds with potential therapeutic applications.
3-ethyl-5-methoxy-1H-indole structure
3-ethyl-5-methoxy-1H-indole structure
Product Name:3-ethyl-5-methoxy-1H-indole
CAS No:2433-68-3
MF:C11H13NO
MW:175.227022886276
MDL:MFCD20662223
CID:1419804
PubChem ID:12474015
Update Time:2025-06-08

3-ethyl-5-methoxy-1H-indole Chemical and Physical Properties

Names and Identifiers

    • 1H-Indole, 3-ethyl-5-methoxy-
    • 3-ethyl-5-methoxy-indole
    • SCHEMBL178561
    • SY150818
    • AKOS026121370
    • EN300-124986
    • MFCD20662223
    • Z1262565884
    • 3-ethyl-5-methoxy-1H-indole
    • CAA43368
    • 3-ethyl-5-methoxyindole
    • DTXSID701309921
    • 2433-68-3
    • MDL: MFCD20662223
    • Inchi: 1S/C11H13NO/c1-3-8-7-12-11-5-4-9(13-2)6-10(8)11/h4-7,12H,3H2,1-2H3
    • InChI Key: WBXDOYUGTWZQBA-UHFFFAOYSA-N
    • SMILES: O(C)C1C=CC2=C(C=1)C(=CN2)CC

Computed Properties

  • Exact Mass: 175.09979
  • Monoisotopic Mass: 175.099714038g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 172
  • 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: 2
  • Topological Polar Surface Area: 25?2

Experimental Properties

  • PSA: 25.02

3-ethyl-5-methoxy-1H-indole Pricemore >>

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Additional information on 3-ethyl-5-methoxy-1H-indole

1H-Indole, 3-ethyl-5-methoxy- (CAS No. 2433-68-3): A Comprehensive Overview of Its Applications and Recent Research Findings

1H-Indole, 3-ethyl-5-methoxy- is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology due to its diverse biological activities and structural versatility. With a Chemical Abstracts Service (CAS) number of 2433-68-3, this compound belongs to the indole family, which is well-known for its role in various natural products and bioactive molecules. The presence of ethyl and methoxy substituents at the 3rd and 5th positions, respectively, enhances its pharmacological potential, making it a valuable scaffold for drug discovery and development.

The< strong>indole core is a crucial structural motif in many biologically active compounds, including several FDA-approved drugs. Its aromaticity and ability to engage in hydrogen bonding make it an ideal platform for designing molecules with specific interactions with biological targets. The< strong>3-ethyl-5-methoxy substitution pattern introduces additional functional groups that can modulate the electronic properties and reactivity of the indole ring, thereby influencing its biological activity.

In recent years, there has been a surge in research focusing on indole derivatives as potential therapeutic agents. One of the most compelling areas of investigation has been their role in modulating immune responses and inflammation. Studies have demonstrated that certain indole derivatives can activate or inhibit specific signaling pathways involved in immune regulation. For instance, derivatives of< strong>1H-indole, 3-ethyl-5-methoxy- have shown promise in preclinical models for their ability to modulate cytokine production and immune cell function.

Another significant area of research involves the use of< strong>1H-indole, 3-ethyl-5-methoxy- as a precursor in the synthesis of more complex pharmacophores. Its structural features make it an excellent starting point for constructing molecules with enhanced binding affinity and selectivity towards target enzymes or receptors. Researchers have leveraged its< strong>ethyl and< strong>methoxy groups to fine-tune the pharmacokinetic properties of drug candidates, improving their bioavailability and metabolic stability.

The< strong>CAS No. 2433-68-3 identifier ensures that researchers can reliably source this compound for their studies while maintaining consistency across different batches. This standardization is crucial for reproducibility in scientific research, particularly in pharmaceutical development where small variations can significantly impact experimental outcomes.

In addition to its immunomodulatory potential, 1H-indole, 3-ethyl-5-methoxy- has been explored for its anticancer properties. Preclinical studies have indicated that certain derivatives can induce apoptosis in cancer cells by interfering with critical signaling pathways such as the PI3K/Akt pathway. The< strong>methoxy group in particular has been shown to enhance the solubility and cellular uptake of these derivatives, making them more effective as therapeutic agents.

The versatility of< strong>1H-indole, 3-ethyl-5-methoxy- also extends to its role as an intermediate in the synthesis of agrochemicals. Its structural framework can be modified to produce compounds with herbicidal or fungicidal properties, contributing to sustainable agricultural practices. By optimizing the substitution pattern on the indole ring, chemists can develop novel agrochemicals that are both effective and environmentally friendly.

The synthesis of< strong>1H-indole, 3-ethyl-5-methoxy- typically involves multi-step organic reactions that require careful optimization to achieve high yields and purity. Common synthetic routes include Friedel-Crafts alkylation followed by methylation or etherification at specific positions on the indole core. Advances in catalytic methods have further streamlined these processes, making it more feasible to produce this compound on an industrial scale.

The pharmacological evaluation of< strong>CAS No. 2433-68-3-identified compounds often involves both in vitro and in vivo assays to assess their biological activity and safety profiles. High-throughput screening (HTS) technologies have been particularly valuable in identifying lead compounds from large libraries of indole derivatives. These screens allow researchers to rapidly test thousands of molecules for their ability to interact with specific targets, accelerating the drug discovery process.

In conclusion,< strong>1H-indole, 3-ethyl-5-methoxy-, with its CAS number 2433-68-3, represents a promising scaffold for developing novel therapeutic agents across various disease areas. Its unique structural features and biological activities make it a valuable compound for both academic research and industrial applications. As our understanding of its pharmacological properties continues to grow, so too will its potential as a cornerstone molecule in medicinal chemistry.

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