159013-94-2

Usage

Uses

Used in Pharmaceutical Industry:
1,2,5-Oxadiazole-3-carboxylic acid, 4-amino-, methyl ester (9CI) is used as a key intermediate in the synthesis of various biologically active compounds for medicinal applications. Its presence in the molecular structure can enhance the pharmacological properties of the final drug, such as potency, selectivity, and bioavailability.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 1,2,5-Oxadiazole-3-carboxylic acid, 4-amino-, methyl ester (9CI) is utilized as a valuable building block for the design and synthesis of novel drug candidates. Its unique structural features, including the oxadiazole ring and the carboxylic acid group, allow researchers to explore its potential in the development of new therapeutic agents with improved efficacy and reduced side effects.
Used in Drug Development:
1,2,5-Oxadiazole-3-carboxylic acid, 4-amino-, methyl ester (9CI) plays a crucial role in drug development, as it can be incorporated into the molecular structure of potential drug candidates. Its presence can contribute to the optimization of drug properties, such as solubility, stability, and pharmacokinetics, ultimately leading to the discovery of more effective and safer medications.

InChI:InChI=1/C4H5N3O3/c1-9-4(8)2-3(5)7-10-6-2/h1H3,(H2,5,7)

Upstream product

• 67-56-1 methanol 
• 78350-50-2 4-amino-1,2,5-oxadiazole-3-carboxylic acid 

Downstream Products

• 1527497-73-9 methyl 4-([1,2,4]triazolo[4,3-b][1,2,4,5]tetrazin-6-ylamino)-furazan-3-carboxylate 
• 246048-72-6 3-Aminofurazan-4-carboxylic acid hydrazide 

Relevant academic research and scientific papers

Discovery of Selective Small-Molecule Inhibitors for the β-Catenin/T-Cell Factor Protein-Protein Interaction through the Optimization of the Acyl Hydrazone Moiety

Acyl hydrazone is an important functional group for the discovery of bioactive small molecules. This functional group is also recognized as a pan assay interference structure. In this study, a new small-molecule inhibitor for the β-catenin/Tcf protein-protein interaction (PPI), ZINC02092166, was identified through AlphaScreen and FP assays. This compound contains an acyl hydrazone group and exhibits higher inhibitory activities in cell-based assays than biochemical assays. Inhibitor optimization resulted in chemically stable derivatives that disrupt the β-catenin/Tcf PPI. The binding mode of new inhibitors was characterized by site-directed mutagenesis and structure-activity relationship studies. This series of inhibitors with a new scaffold exhibits dual selectivity for β-catenin/Tcf over β-catenin/cadherin and β-catenin/APC PPIs. One derivative of this series suppresses canonical Wnt signaling, downregulates the expression of Wnt target genes, and inhibits the growth of cancer cells. This compound represents a solid starting point for the development of potent and selective β-catenin/Tcf inhibitors (Chemical Equation).

Synthesis and X-ray study of novel azofurazan-annulated macrocyclic lactams

Reaction of 1,4-di-(3-aminofurazan-4-oyl)piperazine 4 with dibromoisocyanurate (DBI) affords azofurazan-annulated macrocyclic lactam 7; the X-ray structure of the macrocycle 7 is reported. The synthesis was started with 3-aminofurazan-4-carboxylic acid 1. A one-pot method for preparation of the amino acid was elaborated from commercially available cyanoacetic ester. Amides of the acid have been prepared via the esterification and subsequent amination.

1,3,4-Oxadiazole Bridges: A Strategy to Improve Energetics at the Molecular Level

Many energetic materials synthesized to date have limited applications because of low thermal and/or mechanical stability. This limitation can be overcome by introducing structural modifications such as a bridging group. In this study, a series of 1,3,4-oxadiazole-bridged furazans was prepared. Their structures were confirmed by 1H and 13C NMR, infrared, elemental, and X-ray crystallographic analyses. The thermal stability, friction sensitivity, impact sensitivity, detonation velocity, and detonation pressure were evaluated. The hydroxylammonium salt 8 has an excellent detonation performance (D=9101 m s?1, P=37.9 GPa) and insensitive properties (IS=17.4 J, FS=330 N), which show its great potential as a high-performance insensitive explosive. Using quantum computation and crystal structure analysis, the effect of the introduction of the 1,3,4-oxadiazole moiety on molecular reactivity and the difference between the sensitivities and thermal stabilities of mono- and bis-1,3,4-oxadiazole bridges are considered. The synthetic method for introducing 1,3,4-oxadiazole and the systematic study of 1,3,4-oxadiazole-bridged compounds provide a theoretical basis for future energetics design.

Azo1,3,4-oxadiazole as a Novel Building Block to Design High-Performance Energetic Materials

In this study, the azo1,3,4-oxadiazole energetic fragment was first introduced into the energetic materials using a simple synthetic strategy, yielding two symmetrical covalent compounds 4 and 5. All new compounds (3-5) were well-characterized by IR spectroscopy, NMR spectroscopy, thermal analysis, and single-crystal X-ray diffraction analysis. As supported by differenctial scanning calorimetry data, compounds 4 and 5 possess excellent decomposition temperatures as high as 248 and 278 °C, respectively. To the best of our knowledge, 278 °C ranks highest in all 1,3,4-oxadiazole-based energetic compounds. Their energetic performances were evaluated with EXPLO5. Both 4 and 5 show good detonation velocities (D) of 8409 and 8800 m s-1 and detonation pressures (P) of 29.3 and 35.1 GPa, comparable to RDX (D: 8795 m s-1, P: 34.9 GPa). Furthermore, on the basis of the single-crystal data, quantum-chemical calculations were employed to better understand their intrinsic structure-property relationship. All these positive results indicate the superior potential of the azo1,3,4-oxadiazole backbone for designing next generation of energetic materials.

METHODS AND COMPOSITIONS OF SUBSTITUTED 5H-[1,2,5]OXADIAZOLO[3',4':5,6] PYRAZIONO[2,3-B]INDOLE ANALOGS AS INHIBITORS OF BETA-CATENIN/T-CELL FACTOR PROTEIN-PROTEIN INTERACTIONS

In one aspect, the invention relates to substituted 5H-[1,2,5]oxadiazolo [3',4':5,6]pyrazino[2,3-b]indole analogues, derivatives thereof, and related compound; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders, e.g., various tumors and cancers, associated with a β-catenin/T-cell factor interaction dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.