5228-49-9

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-5-NITRO-1H-INDAZOLE is used as a key intermediate in the synthesis of various drugs, particularly for the development of anti-inflammatory and anti-cancer medications. Its unique chemical structure and biological activities contribute to the discovery and design of novel therapeutic agents.
Used in Anti-inflammatory Applications:
1-METHYL-5-NITRO-1H-INDAZOLE is used as an anti-inflammatory agent for the treatment of various inflammatory conditions. Its potential therapeutic effects are attributed to its ability to modulate inflammatory pathways and reduce inflammation-related symptoms.
Used in Anti-cancer Applications:
1-METHYL-5-NITRO-1H-INDAZOLE is used as an anti-cancer agent for the treatment of various types of cancer. Its potential therapeutic effects are due to its ability to inhibit cancer cell growth and proliferation, as well as its potential to enhance the efficacy of conventional chemotherapeutic drugs.
Used in Antimicrobial Applications:
1-METHYL-5-NITRO-1H-INDAZOLE is used as a potential antibacterial agent for the treatment of bacterial infections. Its antimicrobial properties have been studied, and it has shown promise in inhibiting the growth of various bacterial strains, making it a valuable candidate for further research and development in the field of antimicrobial chemotherapy.

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

Upstream product

• 77-78-1 dimethyl sulfate 
• 5401-94-5 5-nitroindazole 
• 74-88-4 methyl iodide 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 7597-18-4 6-nitroindazole 
• 73105-48-3 1-methyl-5-nitro-1H-indazol-3-ylamine 
• 17417-09-3 2-fluoro-5-nitrobenzonitrile 

Downstream Products

• 50593-24-3 1-methyl-1H-indazol-5-amine 
• 1620816-81-0 7-(4-methoxyphenyl)-1-methyl-5-nitro-3-phenyl-1H-indazole 
• 1620816-82-1 7-(4-(trifluoromethyl)phenyl)-1-methyl-5-nitro-3-phenyl-1H-indazole 
• 1620816-64-9 1-methyl-5-nitro-3,7-diphenyl-1H-indazole 
• 1620816-83-2 ethyl 4-(1-methyl-5-nitro-3-phenyl-1H-indazol-7-yl)benzoate 
• 1620816-84-3 1-methyl-5-nitro-3-phenyl-7-o-tolyl-1H-indazole 
• 1620816-85-4 1-methyl-5-nitro-3-phenyl-7-m-tolyl-1H-indazole 
• 1620816-73-0 1-methyl-5-nitro-3-phenyl-7-p-tolyl-1H-indazole 
• 728035-42-5 1-methyl-5-nitro-3-phenyl-1H-indazole 
• 1429924-44-6 3,8-dimethyl-3H-pyrazolo[4,3-a]acridine-11-carbonitrile 

Relevant academic research and scientific papers

Synthesis of new fluorescent pyrazolo[4,3-a]acridine derivatives having strong antibacterial activities

New 3H-pyrazolo[4,3-a]acridine derivatives have been prepared by the reaction of 1-alkyl-5-nitro-1H-indazole with phenylacetonitrile and 2-(4-bromophenyl)acetonitrile in basic conditions via the nucleophilic substitution of hydrogen and concomitant cyclisation. The new compounds exhibited potent antibacterial activities and their antibacterial activities against Gram positive (Staphylococcus aureus, methicillin resistant S. aureus and Bacillus subtilis) and Gram negative bacterial (Pseudomonas aeruginosa and Escherichia coli) species were determined. The fluorescence properties of these derivatives were also studied.

New heterocyclic green, blue and orange dyes from indazole: Synthesis, tautomerism, alkylation studies, spectroscopic characterization and DFT/TD-DFT calculations

Tautomerism and alkylation studies on the green intermediate 2-(5-hydroxyimino-1-methyl-4,5-dihydro-1H-4-indazolyliden)-2-phenylacetonitrile led to the synthesis of new heterocyclic green, blue and orange dyes in high yields. The structures of all newly s

Synthesis and Some Transformations of 7-(Fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]benzothiazole

N-Methylation of 5-nitro-1H-indazole in a KOH–DMSO system resulted in a mixture of 1-methyl-5(6)-nitroindazoles in a ratio of 1: 2. Reduction of the isomers with tin in concentrated hydrochloric acid afforded pure 1-methyl-1H-indazole-6-amine. Condensation of the latter with furoyl chloride in 2-propanol yielded N-(1-methylindazol-6-yl)furan-2-carboxamide, treatment of which with an excess of P2S5 in anhydrous pyridine gave the corresponding carbothioamide. 7-(Fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]benzothiazole was synthesized by Jacobson oxidation of N-(1-methylindazol-6-yl) furan-2-carbothioamide with potassium ferricyanide in an alkaline medium. Some transformations of 7-(fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]- benzothiazole such as formylation and acylation were performed.

A SUBSTITUTED TETRAHYDROISOQUINOLINE DERIVATIVE AS A D1 POSITIVE ALLOSTERIC MODULATOR

The present invention relates to compound according to formula (I), (I) which is a positive allosteric modulator of D1 and accordingly of benefit as pharmaceutical agent for the treatment of diseases in which D1 receptors play a role.

Discovery of 1-(1H-indazol-4-yl)-3-((1-phenyl-1H-pyrazol-5-yl)methyl) ureas as potent and thermoneutral TRPV1 antagonists

A series of 1-indazol-3-(1-phenylpyrazol-5-yl)methyl ureas were investigated as hTRPV1 antagonists. The structure–activity relationship study was conducted systematically for both the indazole A-region and the 3-trifluoromethyl/t-butyl pyrazole C-region to optimize the antagonism toward the activation by capsaicin. Among them, the antagonists 26, 50 and 51 displayed highly potent antagonism with Ki(CAP) = 0.4–0.5 nM. Further, in vivo studies in mice indicated that these derivatives both antagonized capsaicin induced hypothermia, consistent with their in vitro activity, and themselves did not induce hyperthermia. In the formalin model, 51 showed anti-nociceptive activity in a dose-dependent manner.

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 %.

Synthesis, Antiviral, Antibacterial, and Cytotoxicity Assessment of Some 3H-Benzo[a]imidazo[4,5-j]acridines and 3H-Benzo[a]pyrazolo[3,4-j]acridines

Abstract: Some novel 3H-benzo[a]imidazo[4,5-j]acridines and 3H-benzo[a]pyrazolo[3,4-j]acridines were synthesized by the reaction of 1-alkyl-5-nitro-1H-benzoimidazoles and 1-alkyl-5-nitro-1H-indazoles with 1-naphthylacetonitrile in high yields. The structures of the new compounds were determined by spectral (FTIR, 1H, and 13C NMR) and analytical data. The antiviral activity of the synthesized compounds was tested against a panel of DNA and RNA viruses, including herpes simplex virus-1 KOS, vesicular stomatitis virus, herpes simplex virus-2 (G), vaccinia virus, and herpes simplex virus-1 TK-KOS ACVr. Most of the test compounds showed moderate activities in comparison with their corresponding reference standards. The synthesized compounds were also tested for antibacterial activity against a panel of strains of gram-negative and gram-positive bacterial species, and some of them we found as effective against gram- positive bacteria as well-known antibacterial agents, such as Cephalexin. The products we found to be cytostatic in the higher micromolar range.

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, characterisation, optical properties and theoretical calculations of a new fluorescent heterocyclic system: 3H-benzo[a]pyrazolo[3,4-j]acridine

Four new fluorescent dyes derived from the 3H-benzo[a]pyrazolo[3,4-j]acridine system were synthesised and fully characterised by 1H NMR, 13C NMR, mass and analytical data. These new fluorophores were prepared from the reaction of 1-alkyl-5-nitro-1H-indazoles with 1-naphthylacetonitrile via nucleophilic substitution of hydrogen, in high yields. The optical properties of the dyes were also investigated and the results revealed that, in some cases, they have higher quantum yields compared with well-known fluorescent dyes such as fluorescein. Solvent effects on the fluorescence characteristics of the four compounds indicated that the emission wavelength is red-shifted with increasing solvent polarity. Furthermore, density functional theory calculations using the B3LYP hybrid functional and the 6-311++G(d,p) basis set provided the optimised geometries and relevant frontier orbitals of the compounds. Calculated electronic absorption spectra were also obtained using the time-dependent density functional theory method.

HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.