2942-42-9

Usage

Uses

Used in Pharmaceutical Applications:
7-Nitroindazole is used as a specific inhibitor of neural nitric oxide synthase (nNOS) for its role in modulating hippocampal long-term potentiation (LTP) and general cell signaling. It is particularly useful in research and therapeutic applications targeting the NOS enzyme, which is involved in various physiological and pathological processes.
Used in Pain Management:
7-Nitroindazole is used as an anti-nociceptive agent for its ability to alleviate pain without affecting blood pressure. This makes it a valuable compound in the development of pain management therapies, especially for conditions where blood pressure regulation is a concern.
Used in Neurological Research:
7-Nitroindazole is used as a research tool for studying the role of nitric oxide (NO) in neuronal tissue and its involvement in various neurological processes, such as LTP and cell signaling. Its specificity as an inhibitor of nNOS makes it a valuable asset in understanding the complex interactions within the nervous system.
Used in Drug Development:
7-Nitroindazole serves as a starting point for the development of new drugs targeting the NOS enzyme family. Its potent and selective inhibition of nNOS makes it a promising candidate for the creation of novel therapeutics for neurological disorders and pain management.
Used in Chemical Synthesis:
7-Nitroindazole can be used as a chemical intermediate in the synthesis of other related compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science. Its unique chemical properties and reactivity make it a versatile building block for the development of new molecules with specific functions and properties.

Biological Activity

Sodium salt of the non-selective NOS inhibitor 7-nitroindazole (7-Nitroindazole).

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

Upstream product

• 570-24-1 2-Methyl-6-nitroaniline 
• 7732-18-5 water 
• 5274-70-4 3-nitrosalicylic aldehyde 
• 173459-52-4 1-N-Boc-7-nitroindazole 

Downstream Products

• 58706-36-8 1‐methyl‐7‐nitro‐1H‐indazole 
• 13436-58-3 2-methyl-7-nitro-2H-indazole 
• 74209-34-0 3-bromo-7-nitro-1H-indazole 
• 21443-96-9 1H-indazol-7-amine 
• 165668-35-9 4-methoxy-N-(7-indazolyl)benzenesulfonamide 
• 74209-33-9 3-chloro-7-nitro-1H-indazole 
• 90223-02-2 7-amino-2-methyl-2H-indazole 
• 41926-06-1 7-amino-1-methyl-1H-indazole 
• 918961-26-9 4,7-diamine-1H-indazole 

Relevant academic research and scientific papers

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 and biological evaluation of indazole-4,7-dione derivatives as novel BRD4 inhibitors

Bromodomain-containing protein 4 (BRD4) is known to regulate the expression of c-Myc to control the proliferation of cancer cells. Therefore, development of small-molecule inhibitors targeting the bromodomain has been widely studied. However, some clinical trials on BRD4 inhibitors have shown its drawbacks such as toxicity including the loss of organ weight. Here, we report the development of the novel and promising scaffold, 1H-indazol-4,7-dione, as a bromodomain inhibitor and synthesized derivatives for the inhibition of binding of bromodomain to acetylated histone peptide. Through this effort, we obtained 6-chloro-5-((2,6-difluorophenyl)amino)-1H-indazole-4,7-dione (5i), which showed a highly potent activity with a half-maximal inhibitory concentration (IC50) of 60?nM. The in vivo xenograft assay confirmed that the 1H-indazol-4,7-dione compound reduced the tumor size significantly. These results show that the 1H-indazol-4,7-dione scaffold is highly potent against bromodomain.

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.

SUBSTITUTED AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions (formula (I)).

An efficient synthesis of 1-H indazoles

The reaction of substituted salicyaldehydes with hydrazine hydrochloride under different conditions gave the corresponding 1-H indazoles. However, the reaction of benzaldehydes with hydrazine hydrate under the same conditions yielded only hydrazones.

Efficient synthesis of 7-substituted or 3,7-disubstituted 1H-indazoles

This work reports on the synthesis of the novel indazole scaffolds 7-OTf-1H-indazole (trifluoromethanesulfonic acid 1H-indazol-7-yl ester), 7-iodo-1H-indazole and 3-bromo-7-iodo-1H-indazole. These new compounds are potent building blocks in divergent syntheses of indazoles via palladium cross-coupling reactions. Georg Thieme Verlag Stuttgart.

A mild and selective method for the N-Boc deprotection by sodium carbonate

A cleavage of N-tert-butyloxycarbonyl protection by Na2CO3 is reported. The N-free products are obtained in excellent yields. The compatibility of the method with the presence of acidic or basic groups is demonstrated. The reactions were performed on indole, azaindole, indazole, pyrazole, indolinone, quinolinone, and oxazolone.

Heterocyclic substituted 2-methyl-benzimidazole antiviral agents

The present invention concerns antiviral compounds, their methods of preparation and their compositions, and use in the treatment of viral infections. More particularly, the invention provides heterocyclic substituted 2-methylbenzimidazole derivatives for the treatment of respiratory syncytial virus infection.

Radical scavenging by N-aminoazaaromatics

N-Aminoazaaromatics were found to react with nitric oxide in the presence of oxygen to afford deaminated products in high yields. The reaction proceeded almost instantaneously in various solvents including water, and one to two equivalent of NO was consumed depending upon the amount of oxygen coexisted, and 1 equivalent of N2O was released in the reaction. In addition, N-aminoazoles were deaminated by potassium superoxide to give parent azoles in good yields. Two equivalents of superoxide was consumed, and about half equivalents of both nitrite and nitrate ion were released. The results demonstrated that N-aminoazoles have ability to protect the biological system against the oxidation promoted by radicals such as nitrogen oxides and superoxide. Copyright (C) 2000 Elsevier Science Ltd.

Research in 7-aminoindazole series: Synthesis of new halo-7H-4-methylpyrazolo[1,5,4-ef][1,5]benzodiazepin-6-ones and 5H-9-halo-6-methylpyrazolo[1,5,4-ef][1,5]benzodiazepin-4-ones

A new class of 7-aminohaloindazoles has been synthesized. Reactivity of the amino groups of these bicyclic systems has been investigated. The halogenated pyrazolo-1,5-benzodiazepinones have been synthesized by the condensation of 7-aminoindazoles with ethyl acetoacetate.