Cas no 1224593-92-3 (Ethyl 3-nitroisoxazole-5-carboxylate)

Ethyl 3-nitroisoxazole-5-carboxylate structure
1224593-92-3 structure
Product Name:Ethyl 3-nitroisoxazole-5-carboxylate
CAS No:1224593-92-3
MF:C6H6N2O5
MW:186.12224149704
CID:1090672
PubChem ID:22601916
Update Time:2025-07-18

Ethyl 3-nitroisoxazole-5-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 3-nitroisoxazole-5-carboxylate
    • ethyl 3-nitro-1,2-oxazole-5-carboxylate
    • SCHEMBL6889005
    • DTXSID10626811
    • Ethyl3-nitroisoxazole-5-carboxylate
    • 1224593-92-3
    • MDL: MFCD27923146
    • Inchi: 1S/C6H6N2O5/c1-2-12-6(9)4-3-5(7-13-4)8(10)11/h3H,2H2,1H3
    • InChI Key: ZKRTWKLPHNQQOX-UHFFFAOYSA-N
    • SMILES: O(C(C1=CC([N+](=O)[O-])=NO1)=O)CC

Computed Properties

  • Exact Mass: 186.02767130g/mol
  • Monoisotopic Mass: 186.02767130g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 4
  • Complexity: 214
  • 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: 1.1
  • Topological Polar Surface Area: 98.2?2

Ethyl 3-nitroisoxazole-5-carboxylate Pricemore >>

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Additional information on Ethyl 3-nitroisoxazole-5-carboxylate

Ethyl 3-nitroisoxazole-5-carboxylate (CAS No. 1224593-92-3): An Overview of Its Structure, Synthesis, and Applications in Pharmaceutical Research

Ethyl 3-nitroisoxazole-5-carboxylate (CAS No. 1224593-92-3) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique isoxazole ring and nitro functional group, exhibits a range of properties that make it a valuable intermediate in the synthesis of various bioactive molecules.

The structure of ethyl 3-nitroisoxazole-5-carboxylate is composed of an isoxazole ring, which is a five-membered heterocyclic compound containing one oxygen and one nitrogen atom. The presence of the nitro group at the 3-position and the carboxylate ester at the 5-position imparts specific chemical reactivity and biological activity to the molecule. The ethyl group attached to the carboxylate ester further influences its solubility and reactivity profiles.

In terms of synthesis, ethyl 3-nitroisoxazole-5-carboxylate can be prepared through several well-established methods. One common approach involves the reaction of ethyl acetoacetate with hydroxylamine hydrochloride to form an intermediate, which is then cyclized in the presence of an acid catalyst to yield the desired isoxazole derivative. Subsequent nitration of the isoxazole ring using a mixture of nitric and sulfuric acids introduces the nitro group at the 3-position. This synthetic route has been optimized for high yields and purity, making it suitable for large-scale production in industrial settings.

Recent studies have highlighted the potential applications of ethyl 3-nitroisoxazole-5-carboxylate in pharmaceutical research. For instance, its ability to act as a precursor in the synthesis of antibacterial agents has been explored. The nitro group can be reduced to an amino group, leading to compounds with enhanced antibacterial activity against both Gram-positive and Gram-negative bacteria. Additionally, derivatives of this compound have shown promise as inhibitors of specific enzymes involved in various disease pathways, such as kinases and proteases.

Another area of interest is the use of ethyl 3-nitroisoxazole-5-carboxylate in the development of anti-inflammatory drugs. The isoxazole ring structure is known to exhibit anti-inflammatory properties, and modifications to this core structure can enhance these effects. Research has shown that compounds derived from this scaffold can effectively inhibit pro-inflammatory cytokines and enzymes, making them potential candidates for treating inflammatory diseases such as arthritis and asthma.

The pharmacological properties of ethyl 3-nitroisoxazole-5-carboxylate have also been investigated in preclinical studies. These studies have demonstrated that derivatives of this compound can cross biological membranes efficiently, suggesting good bioavailability when administered orally or parenterally. Furthermore, preliminary toxicity assessments have indicated that these compounds are generally well-tolerated at therapeutic doses, with minimal side effects observed.

In conclusion, ethyl 3-nitroisoxazole-5-carboxylate (CAS No. 1224593-92-3) is a promising compound with a wide range of applications in pharmaceutical research. Its unique chemical structure and versatile reactivity make it an attractive candidate for the development of new drugs targeting various diseases. Ongoing research continues to uncover new possibilities for this compound, further solidifying its importance in the field of medicinal chemistry.

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