Cas no 19275-29-7 (2-ethynyl-5-nitrofuran)

2-Ethynyl-5-nitrofuran is a nitrofuran derivative characterized by the presence of an ethynyl group at the 2-position and a nitro group at the 5-position of the furan ring. This compound is of interest in organic synthesis and pharmaceutical research due to its reactive ethynyl moiety, which enables click chemistry applications, and the nitro group, which can facilitate further functionalization. Its structure makes it a potential intermediate for the development of bioactive molecules, including antimicrobial and anticancer agents. The compound's stability and synthetic versatility underscore its utility in medicinal chemistry and material science applications. Proper handling is advised due to its reactive functional groups.
2-ethynyl-5-nitrofuran structure
2-ethynyl-5-nitrofuran structure
Product Name:2-ethynyl-5-nitrofuran
CAS No:19275-29-7
MF:C6H3NO3
MW:137.092921495438
CID:123451
PubChem ID:13158294
Update Time:2025-06-08

2-ethynyl-5-nitrofuran Chemical and Physical Properties

Names and Identifiers

    • Furan,2-ethynyl-5-nitro-
    • 2-ethynyl-5-nitrofuran
    • 2-ETHYNYL-5-NITRO-FURAN
    • DTXSID00523188
    • 5-nitro-2-furylacetylene
    • Furan, 2-ethynyl-5-nitro-
    • 19275-29-7
    • EN300-1854556
    • Inchi: 1S/C6H3NO3/c1-2-5-3-4-6(10-5)7(8)9/h1,3-4H
    • InChI Key: GJXYAJOKVJCOCT-UHFFFAOYSA-N
    • SMILES: O1C(C#C)=CC=C1[N+](=O)[O-]

Computed Properties

  • Exact Mass: 137.01129
  • Monoisotopic Mass: 137.011292958g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 187
  • 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: 1.6
  • Topological Polar Surface Area: 59?2

Experimental Properties

  • PSA: 56.28

2-ethynyl-5-nitrofuran Pricemore >>

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2-ethynyl-5-nitrofuran Related Literature

Additional information on 2-ethynyl-5-nitrofuran

Recent Advances in the Study of 2-Ethynyl-5-Nitrofuran (CAS: 19275-29-7) in Chemical Biology and Pharmaceutical Research

The compound 2-ethynyl-5-nitrofuran (CAS: 19275-29-7) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This heterocyclic compound, characterized by a nitrofuran core with an ethynyl substituent, exhibits notable reactivity and biological activity, making it a promising candidate for drug development and chemical biology studies. Recent studies have explored its role as a versatile building block in medicinal chemistry, as well as its potential as an antibacterial and anticancer agent.

One of the key areas of research involving 2-ethynyl-5-nitrofuran focuses on its mechanism of action and biological targets. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that this compound exhibits potent inhibitory effects against bacterial nitroreductases, enzymes that play a crucial role in antibiotic resistance. The study revealed that the ethynyl group at the 2-position significantly enhances the compound's ability to interact with the active site of these enzymes, suggesting its potential as a novel antibiotic adjuvant to combat resistant bacterial strains.

In the field of cancer research, recent investigations have highlighted the compound's ability to function as a prodrug that is selectively activated in hypoxic tumor environments. A 2024 study in Chemical Science reported that 2-ethynyl-5-nitrofuran can be efficiently reduced by hypoxic tumor cell reductases to generate cytotoxic species, leading to selective tumor cell death while sparing normal cells. This property makes it particularly attractive for developing targeted cancer therapies with reduced side effects.

From a synthetic chemistry perspective, researchers have developed novel methodologies for incorporating 2-ethynyl-5-nitrofuran into more complex molecular architectures. A recent breakthrough published in Organic Letters (2024) described a copper-catalyzed click chemistry approach that enables efficient conjugation of this compound with various biomolecules, opening new possibilities for creating targeted drug delivery systems and chemical probes for biological studies.

The compound's safety profile and pharmacokinetic properties have also been the subject of recent investigations. While early studies indicate good stability and reasonable bioavailability, ongoing research is focusing on optimizing its formulation to improve solubility and tissue distribution. Several research groups are currently exploring nanoparticle-based delivery systems to enhance the therapeutic potential of 2-ethynyl-5-nitrofuran derivatives.

Looking forward, the unique properties of 2-ethynyl-5-nitrofuran (CAS: 19275-29-7) position it as a versatile scaffold for multiple therapeutic applications. Current research directions include the development of novel antimicrobial agents, hypoxia-activated prodrugs, and chemical tools for studying redox biology. As understanding of its molecular interactions deepens, this compound is expected to play an increasingly important role in both drug discovery and chemical biology research.

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