5228-51-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
1-Ethyl-5-nitro-1H-indazole is used as a precursor in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides. Its unique chemical structure allows for the creation of a wide range of compounds with different therapeutic and pesticidal properties.
Used in Antibacterial and Antifungal Applications:
1-Ethyl-5-nitro-1H-indazole is studied for its potential antibacterial and antifungal properties, making it a candidate for the development of new antimicrobial agents. Its ability to target and inhibit the growth of harmful microorganisms could lead to the creation of effective treatments for various infections.
Used in Material Science:
1-Ethyl-5-nitro-1H-indazole has been investigated for its potential use in the development of new materials, owing to its unique chemical and physical properties. Its incorporation into various materials could enhance their performance and open up new applications in different industries.
Used as a Reagent in Organic Chemistry Reactions:
1-Ethyl-5-nitro-1H-indazole serves as a valuable reagent in organic chemistry, facilitating a range of chemical reactions and transformations. Its versatility and reactivity make it a useful tool for chemists in the synthesis of complex organic molecules and the development of novel chemical processes.

Upstream product

• 5401-94-5 5-nitroindazole 
• 74-96-4 ethyl bromide 
• 75-03-6 ethyl iodide 

Downstream Products

• 511249-17-5 5-amino-1-ethyl-1H-indazole 

Relevant academic research and scientific papers

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.

Corey-Chaykovsky Cyclopropanation of Nitronaphthalenes: Access to Benzonorcaradienes and Related Systems

Nitronaphthalene derivatives react as Michael acceptors in the Corey-Chaykovsky reaction with alkyl phenyl selenones and alkyl diphenyl sulfonium salts. Mechanistic studies reveal that sterically demanding substituents at the carbanionic center favor formation of cyclopropanes and suppress competitive β-elimination to the alkylated products. The transformation, demonstrated also on heterocyclic nitroquinoline and nitroindazolines, is an example of transition metal-free dearomatization method.

TRIAZOLO PYRIDINES AS MODULATORS OF GAMMA-SECRETASE

The present invention relates to triazolo pyridines of formula (II) and their use as modulators of ?-secretase. In particular, the present invention relates to compounds which interfere with ?-secretase and/or its substrate and therefore modulate the form

Discovery of tetrahydroindazoles as a novel class of potent and in vivo efficacious gamma secretase modulators

The identification and optimization of a novel series of centrally efficacious gamma secretase modulators (GSMs) offering an alternative to the privileged aryl imidazole motif is described. Chiral bicyclic tetrahydroindazolyl amine substituted triazolopyr

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.

Pyrazolo[4,3-a]quinindoline as a new highly fluorescent heterocyclic system: Design, synthesis, spectroscopic characterization and DFT calculations

(Chemical Equation Presented) After obtaining the desired precursors in several reactions, new N-alkyl-substituted heterocyclic system pyrazolo[4,3-a]quinindolines (pyrazolo[4,3-f]-indolo[2,3-b]quinolines) were synthesized by one-pot reaction of 1-alkyl-5-nitro-1H-indazole with 2-(1-alkyl-1H-3-indolyl)acetonitrile in MeOH/KOH solution via the nucleophilic substitution of hydrogen in excellent yields. Spectral (UV-Vis, FT-IR, NMR and fluorescence) and analytical data allowed the structures of the synthesized compounds to be established. The values of absorption and fluorescence maxima, extinction coefficients and fluorescence quantum yield of these new heterocyclic fluorophores were obtained and they show highlighting interesting photophysical properties. Density functional theory (DFT) calculations of one structure by using the B3LYP hybrid functional and the 6-311 + G(d,p) basis set were performed to provide the optimized geometry, relevant frontier orbitals and the prediction of 1H NMR chemical shifts. Calculated electronic absorption spectrum of one structure was also obtained by time-dependent density functional theory (TD-DFT) method. Solvatochromic properties of these dyes have been discussed and the results showed that the absorption and emission bands in polar solvents undergo a modest red shift.

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.

Design, synthesis, fluorescence properties and antibacterial activities of new 8-chloro-3-alkyl-3h-pyrazolo[4,3-a]acridine-11-carbonitriles

The treatment of alkylated nitro derivatives of indazole with 2-(4-chlorophenyl)acetonitrile under basic conditions gave the new 8-chloro-3-alkyl-3H-pyrazolo[4,3-a]acridine-11-carbonitriles via the nucleophilic substitution of hydrogen which proceeds at room temperature with concomitant cyclisation in fairly good yields. The structures of all newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectral data. Fluorescence experimental results of all newly synthesized compounds revealed remarkable photoluminescence properties and strong green fluorescence properties. Also, the new compounds exhibited potent antibacterial activity and their antibacterial activity (MIC) against Gram positive (Staphylococcuse aureus methicillin resistant S. aureus and Bacillus subtilis) and negative bacterial (Pseudomonas aeruginosa and Escherichia coli) species were determined.

An expedient, regioselective synthesis of novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their anticancer potential

Several novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their 6-alkyl and 8-alkyl derivatives have been synthesised in high overall yields starting from 5-nitro and 6-nitroindazoles in a three-step route involving the regioselective cyclisation of thioureidoindazoles and indazolyl dithiocarbamates as the key steps. Some assorted thiazoloindazoles have been screened for anticancer properties, which demonstrated the anticancer potential of at least one product, justifying its further follow-up.

INDAZOLE OXAZOLIDINONES AS ANTIBACTERIAL AGENTS

The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof wherein: W is C(=O)NHR1, C(=S)NHR1, or CH2het; Y is H, or CF; R1 is H, C16alkyl, or OC1-6/s