246048-72-6

Usage

Uses

Used in Pharmaceutical Industry:
1,2,5-Oxadiazole-3-carboxylic acid, 4-amino-, hydrazide (9CI) is used as a building block for the synthesis of various pharmacologically active compounds due to its unique chemical structure. Its presence in drug molecules can potentially enhance their therapeutic properties and efficacy.
Used in Organic Chemistry:
In the field of organic chemistry, 1,2,5-Oxadiazole-3-carboxylic acid, 4-amino-, hydrazide (9CI) is utilized for the development of new synthetic methodologies and reactions. Its versatile structure allows for the exploration of novel chemical transformations and the creation of innovative synthetic pathways.
Safety Precautions:
As with any chemical compound, it is essential to follow proper handling and safety precautions when working with 1,2,5-oxadiazole-3-carboxylic acid, 4-amino-, hydrazide (9CI) to ensure the safety of researchers and the environment.

Upstream product

• 159013-94-2 methyl 3-aminofurazan-4-carboxylate 

Downstream Products

• 167281-96-1 3-amino-4-(1,2,3,4-tetrazol-5-yl)furazan 

Relevant academic research and scientific papers

Synthesis and some transformations of 2-[(4-aminofurazan-3-yl)-1H-1,2,4-triazol-5-yl]acetic acid derivatives

Two methods for the synthesis of 1,2,4-triazolylacetic ester bearing an aminofurazanyl substituent at the position 5 were developed. The triazole cycle was formed via the cyclocondensation of 3-aminofurazanecarboxylic acid hydrazide or amidrazone with ethoxycarbonylethyl acetimidate hydrochloride.

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.

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).