58706-36-8

Usage

Uses

Used in Research Applications:
1-METHYL-7-NITROINDAZOLE is used as a research tool for inhibiting neuronal nitric oxide synthase, which aids in understanding the role of nitric oxide in various physiological and pathological processes. This includes the study of neurotransmission, inflammation, and neurodegenerative diseases where nitric oxide plays a crucial role.
Used in Pharmaceutical Development:
1-METHYL-7-NITROINDAZOLE is investigated for its potential therapeutic applications, particularly in conditions such as ischemic stroke and traumatic brain injury. In these conditions, the levels of nitric oxide are implicated in the pathological process, and the compound's inhibitory effect on nitric oxide production may offer therapeutic benefits.

InChI:InChI=1/C8H7N3O2/c1-10-8-6(5-9-10)3-2-4-7(8)11(12)13/h2-5H,1H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 2942-42-9 7-Nitroindazole 
• 74-88-4 methyl iodide 
• 570-24-1 2-Methyl-6-nitroaniline 

Downstream Products

• 41926-06-1 7-amino-1-methyl-1H-indazole 
• 864724-72-1 4-methoxy-N-(1-methyl-1H-7-indazolyl)-benzenesulfonamide 
• 369652-64-2 2-[(1-methyl-1H-indazol-7-yl)amino]-3-nitrobenzoic acid 
• 1620816-63-8 1‐methyl‐7‐nitro‐3‐phenyl‐1H‐indazole 

Relevant academic research and scientific papers

“On Water” Palladium Catalyzed Direct Arylation of 1H‐Indazole and 1H‐7‐Azaindazole

The C3 direct arylation of 1H-indazole and 1H-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled 1H-indazoles and C3-aryled 1H-7-azaindazoles via a C3 direct arylation using water as solvent. On water, PPh3 was effective as a ligand along with a lower charge of the catalyst Pd(OAc)2 (5 mol%) at 100 oC, leading to C3-aryled 1H-indazoles or C3-aryled 1H-7-azaindazoles in moderate to good yields.

Palladium-Catalyzed Oxidative Arylation of 1H-Indazoles with Arenes

A simple method for the direct Pd(OAc)2-catalyzed oxidative arylation of inactivated 1H-indazole derivatives with simple arenes is reported. This method exhibits good reaction efficiency and good functional-group tolerance. Using the developed method, 28 arylated products were prepared in yields up to 80 %.

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.

SnCl2/RSH: A versatile catalytic system for the synthesis of 4-Alkylsulfanyl-indazole derivatives

The treatment of alkylated nitro derivatives of indazole with stannous chloride in alkanethiol gave after coupling of the obtained amines with 4-methoxybenzenesulfonyl chloride in pyridine the new N-(4-Alkylsulfanylindazol-7-yl)-4-methoxybenzene sulfonamides via the nucleophilic substitution of hydrogen in position 4 of indazole, together with the expected 4-methoxy-N-(indazol-7-yl)-benzenesulfonamides. All the newly synthesized compounds have been characterized by elemental analysis and spectroscopic data.

Palladium-catalyzed direct C7-arylation of substituted indazoles

A novel direct C7-arylation of indazoles with iodoaryls is described using Pd(OAc)2 as catalyst, 1,10-phenanthroline as ligand, and K 2CO3 as base in refluxing DMA. Direct C7-arylation of 3-substituted 1H-indazole containing an EWG on the arene ring gave the expected products in good isolated yields. In addition, a one-pot Suzuki-Miyaura/ arylation procedure leading to C3,C7-diarylated indazoles has been developed.

Fluorinated indazoles as novel selective inhibitors of nitric oxide synthase (NOS): Synthesis and biological evaluation

In order to find new compounds with neuroprotective activity and NOS-I/NOS-II selectivity, we have designed, synthesized, and characterized 14 new NOS inhibitors with an indazole structure. The first group corresponds to 4,5,6,7-tetrahydroindazoles (4-8), the second to the N-methyl derivatives (9-12) of 7-nitro-1H-indazole (1) and 3-bromo-7-nitro-1H-indazole (2), and the latter to 4,5,6,7-tetrafluoroindazoles (13-17). Compound 13 (4,5,6,7-tetrafluoro-3-methyl-1H-indazole) inhibited NOS-I by 63% and NOS-II by 83%. Interestingly, compound 16 (4,5,6,7-tetrafluoro-3-perfluorophenyl-1H-indazole) inhibited NOS-II activity by 80%, but it did not affect to NOS-I activity. Structural comparison between these new indazoles further supports the importance of the aromatic indazole skeleton for NOS inhibition and indicate that bulky groups or N-methylation of 1 and 2 diminish their effect on NOS activity. The fluorination of the aromatic ring increased the inhibitory potency and NOS-II selectivity, suggesting that this is a promising strategy for NOS selective inhibitors.

Inhibitory effects of a series of 7-substituted-indazoles toward nitric oxide synthases: Particular potency of 1H-indazole-7-carbonitrile

A series of new 7-monosubstituted and 3,7-disubstituted indazoles have been prepared and evaluated as inhibitors of nitric oxide synthases (NOS). 1H-Indazole-7-carbonitrile (6) was found equipotent to 7-nitro-1H-indazole (1) and demonstrated preference for constitutive NOS over inducible NOS. By contrast, 1H-indazole-7-carboxamide (8) was slightly less potent but demonstrated a surprising selectivity for the neuronal NOS. Further substitution of 6 by a Br-atom at carbon-3 of the heterocycle enhanced 10-fold the inhibitory effects. Inhibition of NO formation by 6 appeared to be competitive versus both substrate and the cofactor (6R)-5,6,7,8-tetrahydro-l-biopterin (H4B). In close analogies with 1, compound 6 strongly inhibited the NADPH oxidase activity of nNOS and induced a spin state transition of the heme-FeIII. Our results are explained with the help of the X-ray structures that identified key-features for binding of 1 at the active site of NOS.

Reduction of nitroindazoles: Preparation of new amino and chloroamino derivatives

The synthesis of chloroaminoindazoles by the reduction of the nitro group of indazoles using stannous chloride in alcoholic acid solution is reported. Using catalytic hydrogenation with palladium the expected reduction to amino-indazoles occur.{A figure is presented}. Indazole Nitro Reduction Chlorination Aminochloroindazole Heterocycle.

Synthesis and biological evaluation of N-(7-indazolyl)benzenesulfonamide derivatives as potent cell cycle inhibitors

We herein describe a new synthesis of N-(7-indazolyl)benzenesulfonamide derivatives. These compounds were evaluated for their antiproliferative activities toward L1210 murine leukemia cells. One of them, 4-methoxy-N-(3- chloro-7-indazolyl)benzenesulfonamide, was identified as the most potent with an IC50 of 0.44 μM.

Synthesis of 4-substituted and 3,4-disubstituted indazole derivatives by palladium-mediated cross-coupling reactions

The synthesis of 4-substituted indazole derivatives by palladium-mediated cross-coupling reactions was described. Suzuki, Heck, Sonogashira and Stille cross-coupling reactions were used to introduce aryl, vinyl and alkynyl substituents in 4-position of in