6299-39-4

Usage

Uses

Used in Industrial Fluids:
4-NITRO-1H-1,2,3-BENZOTRIAZOLE is used as a corrosion inhibitor for industrial fluids, such as coolants and metalworking fluids. Its ability to prevent corrosion helps in extending the life of machinery and equipment, thereby reducing maintenance costs and downtime.
Used in Plastics and Rubber Industry:
In the plastics and rubber industry, 4-NITRO-1H-1,2,3-BENZOTRIAZOLE serves as a stabilizer. It helps in enhancing the durability and resistance of these materials against environmental factors such as heat, light, and oxygen, ensuring their longevity and performance.
Used in Dyes and Pigments Production:
4-NITRO-1H-1,2,3-BENZOTRIAZOLE is utilized in the production of dyes and pigments due to its chemical properties. It contributes to the development of colorants with specific characteristics, such as brightness, stability, and resistance to fading, which are essential for various applications in textiles, paints, and coatings.

InChI:InChI=1/C6H4N4O2/c11-10(12)5-3-1-2-4-6(5)8-9-7-4/h1-3H,(H,7,8,9)

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 67764-33-4 cyclopentyl nitrite 
• 3694-52-8 2,3-diamino-nitrobenzene 
• 606-22-4 2,6-dinitroaniline 
• 88-73-3 2-Chloronitrobenzene 
• 606-21-3 1-chloro-2,6-dinitrobenzene 

Downstream Products

• 116975-12-3 4-iodo-1H-benzotriazole 
• 18076-61-4 1H-1,2,3-benzotriazol-4-amine 
• 212791-08-7 7-amino-1H-benzotriazol-4-ol 
• 2338-10-5 4,5,6,7-tetrachloro-1H-benzotriazole 
• 128553-15-1 2-<2'-Deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-4-nitro-2H-benzotriazole 
• 128531-23-7 1-<2'-Deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-4-nitro-1H-benzotriazole 
• 128531-24-8 3-<2'-Deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-4-nitro-3H-benzotriazole 
• 26725-51-9 4-hydroxybenzotriazole 
• 66382-33-0 2-(4-nitro-benzotriazol-2-yl)-cyclohexanol 
• 14209-07-5 1-methyl-7-nitro-1H-benzotriazole 
• 89795-90-4 2-methyl-4-nitro-2H-benzotriazole 
• 27799-86-6 1-methyl-4-nitro-1H-benzotriazole 
• 1395320-39-4 1-ethyl-4-nitro-7-[1-(phenylsulfonyl)propyl]-1H-benzotriazole 
• 1395320-43-0 2-ethyl-4-nitro-7-[1-(phenylsulfonyl)propyl]-2H-benzotriazole 

Relevant academic research and scientific papers

CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS

The present invention is directed to compounds of the formula (I) wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS

The present invention is directed to compounds of the formula (I), wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

Facile alkylation of 4-nitrobenzotriazole and its platelet aggregation inhibitory activity

We explored the facile alkylation of 4-nitrobenzotriazole under basic conditions and the synthesized derivatives were tested for their potential ADP induced platelet aggregation inhibition activity in comparison with standard drug ticagrelor (selective P2Y12 inhibitor). The nitro group at 4-position is highly activating toward alkylation reactions (under strong basic conditions) and resulted in formation of degradation product like 3-nitrobenzene-1,2-diamine which make isolation of alkyl products very difficult. We optimized the reaction under mild basic condition (potassium carbonate and DMF) which is devoid of any degradation product. This is perhaps the first report of 4-nitrobenzotriazole derivatives possessing platelet aggregation inhibitory activity. Generally activity increases with increase in length of alkyl chain and 1-alkyl positional isomers were found to be more potent than 2-alkyl isomers. The benzoyl derivative was found to be the most potent [compound 22; (4-Nitro-1H-benzotriazol-1-yl)(phenyl)methanone; IC50 = 0.65 ± 0.10 mM] which may be attributed to electronegative oxygen atom and aromatic ring. Benzyl derivatives [compound 20; 1-Benzyl-4-nitro-1H-benzotriazole; IC50 = 0.81 ± 0.08 mM, compound 21; 2-Benzyl-4-nitro-2H-benzotriazole; IC50 = 0.82 ± 0.19 mM] and sulfonyl derivative [compound 23; 1-[(4-Methylphenyl)sulfonyl]-4-nitro-1H-benzotriazole; IC50 = 0.82 ± 0.19 mM] are also found to be highly active. Furthermore, all compounds possess P2Y12 binding affinity as confirmed by VASP/P2Y12 phosphorylation assay.

Facile synthesis of benzotriazole derivatives using nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica and two room-temperature nitrite ionic liquids

Nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica, 1-butyl-3-methylimidazolium nitrite, and 1-(3-trimethoxysilylpropyl)-3- methylimidazolium nitrite were used as effective reagents for the preparation of benzotriazole derivatives from 1,2-diaminobenzenes at room temperature under mild solvent-free conditions. These ionic liquids play as nitrosonium sources in this procedure.1,2-Diaminobenzene derivatives have been treated with ionic liquids to give the related diaminobenzenes in very good to excellent yields in short reaction times. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the full experimental and spectral details.

INDAZOLE DERIVATIVES AS ADENOSINE MONOPHOSPHATE DEAMINASE (AMPD) INHIBITORS FOR USE IN DIABETES AND RELATED DISEASES OF METABOLIC SYNDROME

Herein, we describe a method for treatment of diabetes and other disorders classified as Metabolic Syndrome. The invention provides novel AMP Deaminase (AMPD) inhibitors comprising novel indazole and benzotriazole derivatives including a phosphorous containing derivative, a carboxylic acid, or an amino acid ester prodrug. The invention also provides support for a novel mechanism of action for the existing drug metformin: direct inhibition of the enzyme AMPD. The inhibition of AMPD in turn activates AMP Kinase, known to be linked to the action of metformin. The invention also makes novel use of a double inhibitor assay allowing identification of selective AMPD inhibitors over ADA inhibitors. The new inhibitors, structurally distinct from metformin, offer selectivity that may obviate side effects known for metformin itself, providing new benefits for diabetes and Metabolic Syndrome.

JNK MODULATORS

Compounds of formula I modulate JNK: wherein X1 and X2 are each simultaneously N or CH;X3 is CH—R2 or N—SO2R, where R is lower alkyl;R1 is aryl or heteroaryl, substituted with 0-3 lower alkyl radicals;R2 is where R3 is H, lower acyl, or an amino acid, or a pharmaceutically acceptable salt thereof.

1H, 13C and 15N NMR spectroscopy and tautomerism of nitrobenzotriazoles

Benzotriazole nitro derivatives were prepared by nitration of the corresponding benzotriazoles and by methylation or cyclization of appropriate nitro-1,2-phenylenediamines. Structures and tautomerism of the nitrobenzotriazoles were studied by multinuclear 1H, 13C, 15N, and 2D NMR spectroscopy and quantum chemistry. Copyright

[1,2,3]Triazolo[4,5-h]quinolones. A new class of potent antitubercular agents against multidrug resistant Mycobacterium tuberculosis strains

In this preliminary study we report the activity of 3-methyl-9-substituted-6-oxo-6,9-dihydro-3H-[1,2,3]-triazolo[4,5-h]quinolone-carboxylic acids and their esters as a new class of antiinfective agents against MDR Mycobacterium tuberculosis. In antitubercular screening against H37Rv and 11 clinically isolated strains of M. tuberculosis several derivatives (1o,3a,c,i,j,p) showed MIC90 in the range 0.5-3.2 μg/mL. 3c showed no cytotoxicity and proved to be the most potent derivative exhibiting MIC90 = 0.5 μg/mL against all M. tuberculosis strains and infected human macrophages (J774-A1) tested.

Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides

The use of an acetylated benzotriazole for the selective protection of the amino groups of cytidine and 2′-deoxycytidine is reported. The use of the acetyl group is of considerable interest industrially in this role, and a single-step protection strategy advantageous in bulk production. 1-Acetyl-4-nitrobenzotriazole was found to readily acetylate the amine of cytidine preferentially over the exposed alcohol functionalities. With adaptation of the protocol, 2′-deoxycytidine was protected using the same reagent. A similar approach was attempted for the benzoylation of adenosine but was found to be unsuitable.

THIADIAZOLES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of Formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and ischemia reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of Formula (IA).