3994-50-1

Usage

Uses

Used in Pharmaceutical Synthesis:
1-METHYL-4-NITROPYRAZOLE is used as a key intermediate in the production of pharmaceuticals for its ability to facilitate the creation of diverse medicinal compounds. Its presence in the synthesis process can enhance the development of new drugs with improved therapeutic properties.
Used in Dye Production:
1-METHYL-4-NITROPYRAZOLE is utilized as a building block in the synthesis of dyes, contributing to the development of a wide range of colorants for various applications, including textiles, plastics, and printing inks.
Used in Energetic Materials Production:
1-METHYL-4-NITROPYRAZOLE is employed as a crucial component in the manufacturing of energetic materials, such as explosives and propellants. Its high reactivity and energy content make it suitable for these high-energy applications, where it plays a critical role in the performance and efficiency of the final products.
Used in Organic Synthesis:
1-METHYL-4-NITROPYRAZOLE is used as a versatile reagent in organic synthesis, enabling the formation of a variety of organic compounds. Its unique chemical properties allow for the creation of new molecules with specific functionalities, expanding the scope of chemical research and development.

InChI:InChI=1/C4H5N3O2/c1-6-3-4(2-5-6)7(8)9/h2-3H,1H3

Upstream product

• 15803-02-8 4-bromo-1-methyl-1H-pyrazole 
• 92534-69-5 1-methyl-4-nitro-1H-pyrazole-5-carboxylic acid 
• 132771-14-3 1-methyl-4-nitro-5-(3-nitrobenzoyl)pyrazole 
• 930-36-9 1-methyl-1H-pyrazole 
• 60-34-4 methylhydrazine 
• 181294-57-5 β-formyl-β-nitroenamine 
• 39806-90-1 4-iodo-1-methyl-1H-pyrazole 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 34461-00-2 nitromalondialdehyde sodium salt 
• 2075-46-9 4-nitro-1H-pyrazole 
• 74-88-4 methyl iodide 

Downstream Products

• 119071-37-3 1-Methyl-4-nitro-5-(tosylmethyl)pyrazol 
• 69843-13-6 1-methyl-4-aminopyrazole 
• 19868-85-0 1-methyl-4-nitro-1H-pyrazol-5-amine 
• 186298-52-2 3-iodo-1-methyl-4-nitro-1H-pyrazole 
• 796845-64-2 tert‐butyl N‐(1‐methyl‐1H‐pyrazol‐4‐yl)carbamate 
• 1050589-65-5 5-benzenesulfonylmethyl-1-methyl-4-nitro-1H-pyrazole 
• 1201916-87-1 4-(4-nitro-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester 
• 1584233-58-8 5-(4-methoxyphenyl)-1-methyl-4-nitro-1H-pyrazole 
• 1584233-59-9 1-(3-(1-methyl-4-nitro-1H-pyrazol-5-yl)phenyl)ethanone 
• 1584233-60-2 1-methyl-4-nitro-5-(3-nitrophenyl)-1H-pyrazole 
• 1584233-61-3 5-(3-methoxyphenyl)-1-methyl-4-nitro-1H-pyrazole 

Relevant academic research and scientific papers

Light-Triggered, Non-Centrosymmetric Self-Assembly of Aqueous Arylazopyrazoles at the Air–Water Interface and Switching of Second-Harmonic Generation

Trans-p-methoxy arylazopyrazole spontaneously forms non-centrosymmetric polar crystals, which reversibly undergo liquefaction upon photoisomerization to the cis-isomer. This liquid cis-isomer has a large electric dipole moment and is highly soluble in water (solubility up to ≈58 mM), which is remarkably higher than that of the trans-isomer (690 μM). Vis-light illumination of the aqueous cis-isomer generates macroscopically oriented, non-centrosymmetric crystals at the air–water interface. Polar crystals are also formed in sandwich glass cells (spacing, 20 μm) upon photo-induced crystallization of the liquid cis-isomer. The trans-crystals thus formed showed second harmonic generation (SHG) whose intensity is switched on/off in response to the photo-induced phase transition.

Synthesis and Biological Profiling of Pyrazolo-Fused 7-Deazapurine Nucleosides

A series of 8-substituted 1-methyl-1,4-dihydropyrazolo[3′,4′:4,5]pyrrolo[2,3-d]pyrimidine (methylpyrazolo-fused 7-deazapurine) ribonucleosides have been designed and synthesized. Two synthetic approaches to the key heterocyclic aglycon 7, (i) a six-step c

Solvatochromism of heteroaromatic compounds: VI. Comparison of the empirical and theoretical approaches to description of solvatochromism in nonspecific solvation of nitropyrazoles

The effect of nonspecific solvation on the long-wave absorption band in the UV spectra of isomeric nitropyrazoles was studied. The aprotic inert and aprotic protophilic solvents exert different spectroscopic effects. In the former solvents, the solvatochr

C-H Amination of Nitro Azaheterocyclic Compounds by Vicarious Nucleophilic Substitution

Various nitro azaheterocyclic compounds were subjected to C H amination by vicarious nucleophilic substitution with 4H-1,2,4-triazol-4-amine (ATA). The aminated products were characterized by NMR, mass spectroscopy, and single-crystal X-ray diffraction an

Discovery of Milvexian, a High-Affinity, Orally Bioavailable Inhibitor of Factor XIa in Clinical Studies for Antithrombotic Therapy

Factor XIa (FXIa) is an enzyme in the coagulation cascade thought to amplify thrombin generation but has a limited role in hemostasis. From preclinical models and human genetics, an inhibitor of FXIa has the potential to be an antithrombotic agent with superior efficacy and safety. Reversible and irreversible inhibitors of FXIa have demonstrated excellent antithrombotic efficacy without increased bleeding time in animal models (Weitz, J. I., Chan, N. C. Arterioscler. Thromb. Vasc. Biol. 2019, 39 (1), 7-12). Herein, we report the discovery of a novel series of macrocyclic FXIa inhibitors containing a pyrazole P2′ moiety. Optimization of the series for (pharmacokinetic) PK properties, free fraction, and solubility resulted in the identification of milvexian (BMS-986177/JNJ-70033093, 17, FXIa Ki = 0.11 nM) as a clinical candidate for the prevention and treatment of thromboembolic disorders, suitable for oral administration.

Design and synthesis of anti-tumor compounds containing ferulic acid-pyrazole skeleton

The invention discloses design and a preparation method of an anti-tumor compound containing a ferulic acid-pyrazole skeleton. The structure of the anti-tumor compound is shown as a formula in the specification.

Novel 1H-pyrazolo[3,4-d]pyrimidin-6-amino derivatives as potent selective Janus kinase 3 (JAK3) inhibitors. Evaluation of their improved effect for the treatment of rheumatoid arthritis

Selective JAK3 inhibitors have been shown to have a potential benefit in the treatment of autoimmune disorders. Here we report the identification of a series of pyrazolopyrimidine derivatives as potent JAK3 inhibitors that exploit a unique cysteine (Cys909) residue in JAK3. Most of these compounds (13k, 13n and 13 t), displayed stronger anti-JAK3 kinase activity and selectivity than tofacitinib. Furthermore, the most active inhibitor 13t (IC50 = 0.1 nM), also exhibited favourable selectivity for JAK3 in a panel of 9 kinases which contain the same cysteine. In a series of cytokinestimulated cellular analysis, compound 13 t, could potently block the JAK3-STAT signaling pathway. Further biological studies, including cellular antiproliferative activity assays and a rat adjuvant-induced arthritis model for in vivo evaluation, also indicated its efficacy and low toxicity in the treatment of rheumatoid arthritis. The results of these experimental explorations suggested that 13t is a promising lead compound for the development of selective JAK3 inhibitor with therapeutic potential in rheumatoid arthritis.

Alkynyl pyrimidine or alkynyl pyridine compound as well as composition and application thereof

The invention relates to alkynyl pyrimidine or alkynyl pyridine compounds represented by a formula (I) or pharmaceutically acceptable salts, isomers, solvates, crystals or prodrugs thereof. The invention also discloses a pharmaceutical composition contain

PYRROLO(PYRAZOLO)PYRIMIDINE DERIVATIVE AS LRRK2 INHIBITOR

The present invention relates to a pyrrolo(pyrazolo)pyrimidine derivative having efficacy as an LRRK2 inhibitor, a preparation method therefor, and a pharmaceutical composition for preventing or treating degenerative brain diseases, containing the same.

Preparation method and application of novel 6-amino-1H-pyrazolo[3,4-d]pyrimidine JAK kinase inhibitors

The present invention provides drugs used for preventing, treating and/or ameliorating autoimmune diseases (such as psoriasis, rheumatoid arthritis, inflammatory enteritis diseases, Sjogren's syndrome, Behcet's disease, multiple sclerosis and systemic lupus erythematosus). The drugs have excellent JAK kinase inhibitory activity. The present invention also provides pharmaceutically acceptable compositions including the above compounds, and methods for preparing the compounds.