Cas no 5094-42-8 (1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide)

1H-Indole-5-carboxylic acid, 2,3-dimethyl-, hydrazide is a specialized organic compound featuring a substituted indole core with a hydrazide functional group. Its structural configuration, including the 2,3-dimethyl substitution and hydrazide moiety, enhances its reactivity and potential utility in synthetic chemistry applications. This compound is particularly valuable as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and heterocyclic derivatives, where its hydrazide group facilitates further derivatization. The dimethyl substitution may also influence steric and electronic properties, improving selectivity in targeted reactions. Its well-defined structure ensures consistent performance in research and industrial processes, making it a reliable building block for complex molecular frameworks.
1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide structure
5094-42-8 structure
Product Name:1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide
CAS No:5094-42-8
MF:C11H13N3O
MW:203.240422010422
MDL:MFCD00458820
CID:373695
PubChem ID:829825
Update Time:2025-06-15

1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide Chemical and Physical Properties

Names and Identifiers

    • 1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide
    • 2,3-DIMETHYL-1 H-INDOLE-5-CARBOXYLIC ACID HYDRAZIDE
    • 2,3-Dimethyl-indol-5-carbonsaeure-hydrazid
    • 2,3-dimethyl-indole-5-carboxylic acid hydrazide
    • AC1LGZWN
    • CTK1H1757
    • Oprea1_018496
    • Oprea1_528785
    • SureCN1061505
    • SCHEMBL1061505
    • SR-01000319126
    • 2,3-dimethyl-1h-indole-5-carboxylic acidhydrazide
    • HMS1704P13
    • 5094-42-8
    • 2,3-dimethyl-1H-indole-5-carbohydrazide
    • AKOS000300687
    • SR-01000319126-1
    • DTXSID20356718
    • 2,3-Dimethyl-1H-indole-5-carboxylic acid hydrazide
    • MDL: MFCD00458820
    • Inchi: 1S/C11H13N3O/c1-6-7(2)13-10-4-3-8(5-9(6)10)11(15)14-12/h3-5,13H,12H2,1-2H3,(H,14,15)
    • InChI Key: ZLLQSKNEZHGOSH-UHFFFAOYSA-N
    • SMILES: O=C(C1C=CC2=C(C=1)C(C)=C(C)N2)NN

Computed Properties

  • Exact Mass: 203.10599
  • Monoisotopic Mass: 203.105862
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 256
  • 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: 70.9
  • XLogP3: 1.3

Experimental Properties

  • Density: 1.3±0.1 g/cm3
  • Refractive Index: 1.672
  • PSA: 70.91

1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide Security Information

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Additional information on 1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide

Recent Advances in the Study of 1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide (CAS: 5094-42-8)

The compound 1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide (CAS: 5094-42-8) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its potential therapeutic applications. This indole derivative, characterized by its unique hydrazide functional group, has been the subject of several studies exploring its biochemical properties, pharmacological activities, and synthetic pathways. The following sections provide a comprehensive overview of the latest research findings related to this compound.

Recent studies have focused on the synthesis and optimization of 1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide, with particular emphasis on improving yield and purity. A 2023 study published in the Journal of Medicinal Chemistry detailed a novel synthetic route that utilizes palladium-catalyzed cross-coupling reactions, achieving a 78% yield with high enantiomeric purity. This advancement is critical for scaling up production and facilitating further pharmacological evaluations.

In terms of pharmacological activity, preliminary in vitro studies have demonstrated that this compound exhibits potent inhibitory effects on specific kinase enzymes implicated in inflammatory pathways. A study conducted by researchers at the University of Cambridge revealed that 1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide effectively suppresses the activity of JAK2 kinases, which are known to play a role in autoimmune diseases. These findings suggest potential applications in the treatment of conditions such as rheumatoid arthritis and psoriasis.

Moreover, recent computational modeling studies have provided insights into the molecular interactions between 1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide and its biological targets. Molecular docking simulations indicate that the hydrazide moiety forms stable hydrogen bonds with key residues in the active site of target proteins, thereby enhancing binding affinity. These computational findings are supported by experimental data from surface plasmon resonance (SPR) assays, which confirm nanomolar-range binding affinities.

Despite these promising results, challenges remain in the development of 1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide as a therapeutic agent. Pharmacokinetic studies have identified issues related to bioavailability and metabolic stability, which are currently being addressed through structural modifications. For instance, a 2024 study published in Bioorganic & Medicinal Chemistry Letters reported the synthesis of prodrug derivatives designed to improve oral absorption and prolong half-life in vivo.

In conclusion, the compound 1H-Indole-5-carboxylicacid, 2,3-dimethyl-, hydrazide (CAS: 5094-42-8) represents a promising candidate for further drug development, particularly in the realm of kinase inhibition and anti-inflammatory therapy. Ongoing research efforts are focused on optimizing its pharmacological profile and addressing existing limitations. Future studies are expected to explore its efficacy in animal models and potential clinical applications, paving the way for its eventual translation into therapeutic use.

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