2942-42-9

Basic information

• Product Name: 7-Nitroindazole
• Synonyms: 7-Nitroindazole, 97% 25MG;7-Nitro-1H-indazole,98%;1H-Indazole, 7-nitro-;7-nitro-1h-indazol;INDAZOLE, 7-NITRO-;7-NITROINDAZOLE;7-NI;7-NITRO-1H-INDAZOLE
• CAS NO: 2942-42-9
• Molecular Formula: C₇H₅N₃O₂
• Molecular Weight: 163.13
• EINECS: 220-934-4
• Product Categories: Indoles and derivatives;Heterocyclic Compounds;All Inhibitors;Indazoles;Inhibitors;Nitric Oxide Reagents;Nitric Oxide;Signalling
• Mol File: 2942-42-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 185-186°C
• Boiling Point: 290.19°C (rough estimate)
• Flash Point: 185.6 °C
• Appearance: Orange-Yellow Solid
• Density: 1.4141 (rough estimate)
• Vapor Pressure: 9.79E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: −20°C
• PKA: 10.03±0.40(Predicted)
• Water Solubility: slightly soluble
• BRN: 6809
• CAS DataBase Reference: 7-Nitroindazole(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Nitroindazole(2942-42-9)
• EPA Substance Registry System: 7-Nitroindazole(2942-42-9)

Safety Data

• Hazard Codes: T
• Statements: 60-40
• Safety Statements: 53-22-36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: NK7962200
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 2942-42-9(Hazardous Substances Data)

Usage

Description

7-Nitroindazole is a non-selective inhibitor of NOS isoforms in vitro. However, it shows good anti-nociceptive effects in vivo without affecting blood pressure via inhibition of eNOS. The IC50 values for inhibition of rat nNOS, bovine eNOS, and rat iNOS are 0.71, 0.78, and 5.8 μM, respectively.

Chemical Properties

yellow powder or Yellow orange solid soluble in DMSO.

Uses

7-nitroindazole is a specific inhibitor of neural nitric oxide synthase (nNOS), an enzyme that converts arginine to citrulline and nitric oxide (NO) in neuronal tissue. NO is a key player in the hippocampal long-term potentiation (LTP) and in general cell signaling.

Definition

7-Nitroindazole is a heterocyclic small molecule containing an indazole ring that has been nitrated at the 7 position. It is a potent, selective brain inhibitor of mouse cerebellar Nitric Oxide Synthase, a hemoprotein enzyme that, in neuronal tissue, converts arginine to citrulline and nitric oxide (NO).

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

• 74209-34-0 3-bromo-7-nitro-1H-indazole 
• 90223-02-2 7-amino-2-methyl-2H-indazole 
• 41926-06-1 7-amino-1-methyl-1H-indazole 
• 173459-52-4 1-N-Boc-7-nitroindazole 
• 58706-36-8 1‐methyl‐7‐nitro‐1H‐indazole 
• 13436-58-3 2-methyl-7-nitro-2H-indazole 
• 864724-72-1 4-methoxy-N-(1-methyl-1H-7-indazolyl)-benzenesulfonamide 
• 369652-62-0 2-(1H-indazol-7-ylamino)-3-nitrobenzoic acid 
• 369652-64-2 2-[(1-methyl-1H-indazol-7-yl)amino]-3-nitrobenzoic acid 
• 74209-37-3 3-bromo-1-methyl-7-nitro-1H-indazole 
• 864724-82-3 N-(3-iodo-4-(2-trimethylsilanyl-ethoxy)-1-methyl-1H-7-indazolyl)-4-methoxybenzene sulfonamide 

Relevant articles and documents

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.

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.

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.