5401-94-5

Usage

Uses

Used in Pharmaceutical Industry:
5-Nitroindazole is used as an inhibitor for Ca2+-calmodulin (CaM)-dependent nitric oxide synthase, which plays a crucial role in various physiological and pathological processes. Its inhibition property makes it a potential candidate for the development of drugs targeting conditions related to nitric oxide synthase dysregulation.
Used in Chemical Synthesis:
5-Nitroindazole serves as a starting material for the synthesis of other nitroindazole derivatives, such as 3,5-dinitroindazole and 2,5-dinitroindazole. These derivatives can be further utilized in the development of new compounds with potential applications in various industries, including pharmaceuticals, materials science, and chemical research.
Used in Research and Development:
As a compound with unique chemical properties, 5-Nitroindazole is used in research and development for studying the effects of nitric oxide synthase inhibition on various biological processes. This can lead to a better understanding of the underlying mechanisms and the development of novel therapeutic strategies for related conditions.
Used in Material Science:
The light yellow crystalline nature of 5-Nitroindazole may have potential applications in material science, particularly in the development of new materials with specific optical, electronic, or structural properties. Further research and development in this area could lead to innovative uses in various industries.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 21, p. 1063, 1984 DOI: 10.1002/jhet.5570210428Organic Syntheses, Coll. Vol. 3, p. 660, 1955

InChI:InChI=1/C7H5N3O2/c11-10(12)6-1-2-7-5(3-6)4-8-9-7/h1-4H,(H,8,9)

Upstream product

• 271-44-3 benzimidazole 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 7697-37-2 nitric acid 
• 129488-09-1 5-nitro-indazole-1-carboxylic acid tert-butyl ester 
• 97-51-8 5-Nitrosalicylaldehyde 
• 27996-87-8 2-fluoro-5-nitrobenzaldehye 
• 84459-32-5 2-bromo-5-nitrobenzaldehyde 
• 19335-11-6 1H-indazol-5-ylamine 

Downstream Products

• 857774-64-2 2-benzoyl-5-nitro-2H-indazole 
• 23856-15-7 (5-nitro-1H-indazol-1-yl)(phenyl)methanone 
• 5228-48-8 2-methyl-5-nitro-2H-indazole 
• 5228-49-9 1-methyl-5-nitro-1H-indazole 
• 4812-45-7 3-chloro-5-nitro-1H-indazole 
• 31208-76-1 5,7-Dinitro-indazol 
• 19335-11-6 1H-indazol-5-ylamine 
• 150187-64-7 5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 
• 114505-90-7 C₁₆H₉N₃O₄ 
• 5228-51-3 1-ethyl-5-nitro-1H-indazole 
• 105147-22-6 5-Nitro-indazole-1-carboxylic acid (2-fluoro-phenyl)-amide 
• 120-12-7 anthracene 
• 595-49-3 2,2-dinitropropane 
• 3964-18-9 2,3-dimethyl-2,3-dinitrobutane 

Relevant academic research and scientific papers

A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates

A CuI-catalyzed, hydrazine-free transformation of 2-(2-bromoarylidene)guanylhydrazone hydrochlorides using Cs2CO3 as a base and DMEDA as a ligand at 120 °C for 5 h delivers substituted 1H-indazoles with yields up to 75%. The C,N double bond configuration of the substrates was determined by NMR experiments and quantum chemical calculations. The reaction mechanism was studied using quantum chemical calculations.

A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides

A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.

THERAPEUTIC INDAZOLES

The invention provides compounds of formula (I): and salts thereof wherein R1-R5 have any of the meanings described in the specification. The compounds are useful for treating bacterial infections (e.g. tuberculosis).

Design, synthesis, biological evaluation and dynamics simulation of indazole derivatives with antiangiogenic and antiproliferative anticancer activity

VEGFR-2 has a pivotal role in promoting cancer angiogenesis. Herein, two series of novel indazole-based derivatives were designed, synthesized and evaluated for their in vitro inhibitory action against VEGFR-2 kinase enzyme. The second series 11a-e exhibited better potency than the first one 7a-d and 8a-f. Compounds 11b, 11c and 11e exhibited the most potent action, with IC50 of 5.4 nM, 5.6 nM and 7 nM, respectively. As a measure of cellular VEGFR-2 inhibition, compounds 11b and 11c showed strong inhibition of human umbilical vein endothelial cells (HUVEC) proliferation with 80% and 99.6% inhibition at 10 μM concentration, respectively. Attempting to interpret SAR of the synthesized compounds, and provide a basis for further optimization; a comprehensive modeling study was implemented. Molecular docking, dynamics simulation and free energy calculation of the synthesized compounds along with known VEGFR-2 inhibitors were applied. The study illustrated the effect of several factors on VEGFR-2 inhibition, such as the interaction with solvent accessible region of the enzyme, the presence of NH linker and the degree of conformational restriction. Finally, our compounds were evaluated for their in vitro anti-proliferative effect against the full NCI panel of cancer cell lines, where compounds 11a and 11c displayed mean GI% of 93 and 130%, respectively, and showed partly a better behavior than the FDA approved drug sorafenib, with respect to activity (GI50) and safety (LC50) against several cell lines. Thus, compound 11c represents a promising candidate for cancer treatment through antiangiogenic dependent and antiangiogenic independent modes of action.

New nitroindazolylacetonitriles: Efficient synthetic access: Via vicarious nucleophilic substitution and tautomeric switching mediated by anions

New N-Alkyl-nitroindazolylacetonitriles were efficiently obtained via vicarious nucleophilic substitution of N-methyl-nitroindazoles with 4-chlorophenoxyacetonitrile. All compounds were fully characterized by NMR and mass spectroscopy techniques and the structures of some of them were additionally confirmed by X-ray diffraction analysis data. Tautomeric switching was observed in this series of nitroindazolylacetonitriles upon addition of basic anions followed by UV-Vis spectrophotometric and 1H-NMR titrations. The formation of tautomeric species induced by anionic species was endorsed by Density Functional Theory calculations.

Synthesis, antifungal activity and qsar of novel pyrazole amides as succinate dehydrogenase inhibitors

We design and synthesize a series of novel pyrazole amides based on the commercialized fungicides and our previous work. The antifungal activity was tested in vitro by mycelial growth inhibition assay. The results show that all the compounds are of antifungal activities against the tested fungi at different levels. Among them, N-(2-(7-bromo-5-chloro-1H-indazol-1-yl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (Vk) exhibited higher antifungal activity than boscalid against two fungi. Molecular docking study revealed that the carbonyl oxygen atom of Vk forms two hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.

Syntheses of 1-aryl-5-nitro-1h-indazoles and a general one-pot route to 1-aryl-1h-indazoles

An efficient route to substituted 1-aryl-1H-indazoles has been developed and optimized. The method involved the preparation of arylhydrazones from acetophenone or benzaldehyde substituted by fluorine at C2 and nitro at C5, followed by deprotonation and nucleophilic aromatic substitution (SNAr) ring closure in 45–90%. Modification of this procedure to a one-pot domino process was successful in the acetophenone series (73–96%), while the benzaldehyde series (63–73%) required a step-wise addition of reagents. A general one-pot protocol for 1-aryl-1H-indazole formation without the limiting substitution patterns required for the SNAr cyclization has also been achieved in 62–78% yields. A selection of 1-aryl-1H-indazoles was prepared in high yield by a procedure that requires only a single laboratory operation.

Preparation method of indazole and application of indazole in medicine synthesis

The invention belongs to the field of chemicals, and relates to a preparation method of indazole and an application of the indazole in medicine synthesis. The invention discloses a preparation method of indazole and an application of the indazole in synthesizing 1H-indazole-3-carboxylic acid, lonidamine, a compound 8, a compound 9, a compound 10, axitinib, YD-3, YC-1 and similar substances thereof.

N-indazole substituted thiourea derivatives and preparation method and application thereof

The invention discloses N-indazole substituted thiourea derivatives and a preparation method and application thereof and belongs to the technical field of chemical medicine.The thiourea derivatives are a series of compounds simultaneously containing the 1H-indazole ring structure and the asymmetrical thiourea structure, and the compounds are not reported in the literature.The bioactivity test result analysis of the thiourea derivatives show that the compounds are good in antioxidant activity, the average scavenging rate is above 80%, the scavenging rate of the compound 12b, the compound 12c, and the compound 12d and the compound 12h is higher than 90%, the scavenging activity IC50 of the compound 12h on DPPH is 0.14mg/mL; part of the target compounds has certain inhibition activity on herpes viruses, vaccinia viruses, reoviruses, Coxsackie viruses, Feline coronary herpes viruses, HIV viruses and the like, and the compound 12c and the compound 12n are high in antivirus activity; the synthesized compounds hopefully have new bioactivity which is not expounded, and a certain material basis is provided for the development of new medicine.

Copper(I) Oxide-Mediated Cyclization of o-Haloaryl N-Tosylhydrazones: Efficient Synthesis of Indazoles

An efficient synthesis of indazoles from readily accessible E/Z mixtures of o-haloaryl N-tosylhydrazones has been developed. The thermo-induced isomerization of N-tosylhydrazones is discussed. A series of valuable indazole derivatives are prepared in good yields, and the method has been successfully applied to the synthesis of the bioactive compounds, lonidamine, AF-2785, axitinib, YC-1 and YD-3.