69000-39-1

Usage

Uses

Used in Pharmaceutical Research and Development:
2-CHLORO-N-(3-METHYLISOXAZOL-5-YL)ACETAMIDE is utilized as a building block for the synthesis of diverse compounds, playing a crucial role in the creation of new pharmaceutical agents. Its structural components, including the chloro, methylisoxazol-5-yl, and acetamide groups, contribute to its versatility and potential in drug design.
Used in Organic Synthesis:
In the realm of organic synthesis, 2-CHLORO-N-(3-METHYLISOXAZOL-5-YL)ACETAMIDE is employed as a reactant due to the reactivity of its chloro group. This feature allows it to participate in various chemical reactions, facilitating the formation of a wide array of organic compounds.
Used in Drug Design:
The presence of the acetamide group in 2-CHLORO-N-(3-METHYLISOXAZOL-5-YL)ACETAMIDE renders it a potential pharmacophore, which is integral to the design of drugs with specific therapeutic effects.
Used in the Development of Novel Drugs:
The unique pharmacological properties conferred by the methylisoxazol-5-yl group make 2-CHLORO-N-(3-METHYLISOXAZOL-5-YL)ACETAMIDE a valuable component in the development of innovative drugs, targeting a range of therapeutic areas.

InChI:InChI=1/C6H7ClN2O2/c1-4-2-6(11-9-4)8-5(10)3-7/h2H,3H2,1H3,(H,8,10)

Upstream product

• 14678-02-5 5-amino-3-methylisoxazole 
• 79-04-9 chloroacetyl chloride 

Relevant academic research and scientific papers

Synthesis, DFT Study, and Antitumor Activity of Some New Heterocyclic Compounds Incorporating Isoxazole Moiety

Thiazolidin-4-one derivative 3 was synthesized by the transformation of chloroacetamide derivative 2 with NH4SCN.The condensation of 3 with p-anisaldehyde afforded the corresponding arylidene derivative 4. Also, the alkylation of chloroacetamide derivative 2 with different heterocyclic compounds was investigated. Annulation of 5-amino-3-methylisoxazole (1) with α-halocarbonyl compounds 12 and 14 furnished pyrrolo[3,2-d]isoxazole and isoxazolo[5,4-b]azepin-6-one derivatives 13 and 15, respectively, while reaction of 1 with 1-chloro-4-(chloromethyl)benzene gave the monoalkylated product 17. The newly synthesized compounds were screened for their antitumor activity, and the geometry optimizations are in a good agreement with the experimentally observed data.

Design, synthesis, kinetic, molecular dynamics, and hypoglycemic effect characterization of new and potential selective benzimidazole derivatives as Protein Tyrosine Phosphatase 1B inhibitors

Protein-tyrosine phosphatase 1B (PTP1B) is a negative regulator of insulin signaling pathway and has been validated as a therapeutic target for type 2 diabetes. A wide variety of scaffolds have been included in the structure of PTP1B inhibitors, one of them is the benzimidazole nucleus. Here, we report the design and synthesis of a new series of di- and tri- substituted benzimidazole derivatives including their kinetic and structural characterization as PTP1B inhibitors and hypoglycemic activity. Results show that compounds 43, 44, 45, and 46 are complete mixed type inhibitors with a Ki of 12.6 μM for the most potent (46). SAR type analysis indicates that a chloro substituent at position 6(5), a β-naphthyloxy at position 5(6), and a p-benzoic acid attached to the linker 2-thioacetamido at position 2 of the benzimidazole nucleus, was the best combination for PTP1B inhibition and hypoglycemic activity. In addition, molecular dynamics studies suggest that these compounds could be potential selective inhibitors from other PTPs such as its closest homologous TCPTP, SHP-1, SHP-2 and CDC25B. Therefore, the compounds reported here are good hits that provide structural, kinetic, and biological information that can be used to develop novel and selective PTP1B inhibitors based on benzimidazole scaffold.

Isoxazole phosphates and phosphonates

Insecticidally active compounds are disclosed, defined by the general formula STR1 in which R is hydrogen or methyl; R1 is hydrogen or methyl; R2 is a member selected from the group consisting of methyl, methoxy, ethyl, and ethoxy; R3 is alkoxy having 1 to 6 carbon atoms; and X is oxygen or sulfur.