Cas no 887593-60-4 (3-(hydrazinylmethyl)quinoline)

3-(Hydrazinylmethyl)quinoline is a versatile quinoline derivative characterized by the presence of a hydrazinylmethyl functional group at the 3-position of the quinoline ring. This structural feature imparts reactivity as a hydrazine-based building block, making it valuable for the synthesis of heterocyclic compounds, pharmaceuticals, and agrochemical intermediates. The compound’s quinoline core offers inherent stability and π-conjugation, while the hydrazinyl group enables selective modifications, such as condensation reactions or chelation with metal ions. Its applications span medicinal chemistry, where it serves as a precursor for bioactive molecules, and materials science, where it may contribute to ligand design. The product is typically handled under controlled conditions due to the reactivity of the hydrazine moiety.
3-(hydrazinylmethyl)quinoline structure
3-(hydrazinylmethyl)quinoline structure
Product Name:3-(hydrazinylmethyl)quinoline
CAS No:887593-60-4
MF:C10H11N3
MW:173.214441537857
CID:713751
PubChem ID:45934269
Update Time:2025-10-28

3-(hydrazinylmethyl)quinoline Chemical and Physical Properties

Names and Identifiers

    • Quinoline,3-(hydrazinylmethyl)-
    • 1-((quinolin-3-yl)methyl)hydrazine
    • quinolin-3-ylmethylhydrazine
    • 3-(hydrazinylmethyl)quinoline
    • DTXSID80672941
    • 887593-60-4
    • EN300-1847018
    • AKOS005169839
    • CS-0286993
    • MDL: MFCD07786373
    • Inchi: 1S/C10H11N3/c11-13-7-8-5-9-3-1-2-4-10(9)12-6-8/h1-6,13H,7,11H2
    • InChI Key: BGQLQINLPFFFKE-UHFFFAOYSA-N
    • SMILES: N1C=C(CNN)C=C2C=CC=CC=12

Computed Properties

  • Exact Mass: 173.095297364g/mol
  • Monoisotopic Mass: 173.095297364g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 160
  • 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
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 50.9?2

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Additional information on 3-(hydrazinylmethyl)quinoline

Professional Introduction to 3-(hydrazinylmethyl)quinoline (CAS No. 887593-60-4)

3-(hydrazinylmethyl)quinoline, identified by the chemical abstracts service number CAS No. 887593-60-4, is a significant compound in the field of pharmaceutical chemistry and bioorganic synthesis. This heterocyclic amine derivative has garnered considerable attention due to its versatile structural framework and potential applications in drug development. The compound’s molecular structure, featuring a quinoline core substituted with a hydrazinylmethyl group, positions it as a valuable intermediate in the synthesis of various pharmacologically active molecules.

The quinoline scaffold is well-documented for its role in medicinal chemistry, particularly in the development of antimicrobial, antimalarial, and anticancer agents. The introduction of the hydrazinylmethyl moiety into this framework introduces reactive sites that can be further functionalized, enabling the creation of complex derivatives with tailored biological activities. This structural feature makes 3-(hydrazinylmethyl)quinoline a promising candidate for further exploration in the design of novel therapeutic agents.

Recent research has highlighted the compound’s potential in addressing challenging therapeutic targets. For instance, studies have demonstrated its efficacy in modulating enzyme activities associated with inflammatory pathways. The hydrazinylmethyl group’s ability to engage in hydrogen bonding and coordinate with metal ions has been exploited to develop inhibitors targeting metalloproteinases, which are implicated in various diseases, including cancer and neurodegenerative disorders. These findings underscore the compound’s significance as a building block for innovative drug candidates.

In addition to its enzymatic interactions, 3-(hydrazinylmethyl)quinoline has shown promise in cellular studies as a scaffold for small-molecule drugs. Its ability to permeate cell membranes and interact with intracellular targets has been leveraged in the development of compounds that exhibit potent antitumor effects. Preclinical trials have indicated that derivatives of this compound can selectively inhibit the proliferation of cancer cells while minimizing toxicity to healthy tissues. Such findings are particularly encouraging given the growing demand for targeted therapies that exhibit high specificity and low systemic side effects.

The synthesis of 3-(hydrazinylmethyl)quinoline involves multi-step organic reactions that require precise control over reaction conditions to ensure high yield and purity. Advanced synthetic methodologies, including catalytic hydrogenation and palladium-catalyzed cross-coupling reactions, have been employed to construct the desired molecular architecture efficiently. These synthetic strategies not only enhance the accessibility of the compound but also provide opportunities for structural modifications to optimize its pharmacological properties.

The compound’s chemical reactivity also makes it a valuable tool in biochemical research. Its ability to form stable complexes with biomolecules has been utilized in structural biology studies to understand protein-ligand interactions at an atomic level. Such insights are crucial for rational drug design, as they provide detailed information on how small molecules interact with their biological targets. This has opened up new avenues for developing drugs with improved binding affinities and selectivities.

From a regulatory perspective, 3-(hydrazinylmethyl)quinoline is subject to standard guidelines for pharmaceutical intermediates, ensuring its safe handling and use in research and industrial settings. Compliance with Good Manufacturing Practices (GMP) and other regulatory frameworks is essential to maintain quality control throughout its lifecycle. This adherence to regulatory standards not only ensures the safety of researchers handling the compound but also supports its transition from laboratory-scale synthesis to larger-scale production for clinical applications.

The future prospects of 3-(hydrazinylmethyl)quinoline are promising, with ongoing research exploring its potential in various therapeutic areas. Innovations in drug delivery systems, such as nanoparticles and targeted prodrugs, are being investigated to enhance its bioavailability and therapeutic efficacy. Collaborative efforts between academic institutions and pharmaceutical companies are likely to accelerate the discovery and development of novel derivatives based on this versatile scaffold.

In conclusion, 3-(hydrazinylmethyl)quinoline (CAS No. 887593-60-4) represents a significant advancement in pharmaceutical chemistry due to its unique structural features and potential applications. Its role as a building block for drug development, coupled with its reactivity and biocompatibility, positions it as a cornerstone in modern medicinal chemistry research. As scientific understanding continues to evolve, it is anticipated that this compound will play an increasingly important role in addressing unmet medical needs across multiple therapeutic disciplines.

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