1798-11-4

Usage

Uses

Used in Plant Growth Regulation:
4-Nitrophenoxyacetic acid is used as a plant growth regulator for its ability to influence and control the growth and development of plants. This application is particularly relevant in the agricultural industry, where it can be employed to enhance crop yields, improve resistance to environmental stressors, and regulate the timing of growth stages.
Used in Chemical Synthesis:
In the chemical industry, 4-Nitrophenoxyacetic acid can be utilized as an intermediate in the synthesis of various compounds, taking advantage of its unique chemical properties and reactivity. This application allows for the creation of a wide range of products, from pharmaceuticals to specialty chemicals, that can benefit from the compound's specific characteristics.
Used in Research and Development:
Due to its plant growth regulatory activity, 4-Nitrophenoxyacetic acid is also used in research and development settings to study the underlying mechanisms of plant growth and development. This can lead to a better understanding of plant biology and the potential for developing new strategies to improve crop production and resilience.
Used in Environmental Applications:
4-Nitrophenoxyacetic acid may also find use in environmental applications, such as in the remediation of contaminated soils or water bodies. Its plant growth regulatory properties could be harnessed to stimulate the growth of specific plant species that can help in the removal of pollutants or the restoration of damaged ecosystems.

Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C8H7NO5/c10-8(11)5-14-7-3-1-6(2-4-7)9(12)13/h1-4H,5H2,(H,10,11)

Upstream product

• 2272-12-0 (4-nitro-phenoxy)-malonic acid 
• 3926-62-3 sodium monochloroacetic acid 
• 824-78-2 4-nitrophenol sodium salt 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 122-59-8 2-phenoxyacetic acid 
• 19076-89-2 ethyl 4-nitrophenoxyacetate 
• 100-02-7 4-nitro-phenol 
• 139024-36-5 1-Imidazol-1-yl-2-(4-nitro-phenoxy)-ethanone 
• 20768-14-3 (4-nitrophenoxy)acetic acid tert-butyl ester 
• 79-11-8 chloroacetic acid 
• 79-08-3 bromoacetic acid 
• 19786-48-2 methyl 2-(4-nitrophenoxy)acetate 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 19076-89-2 ethyl 4-nitrophenoxyacetate 
• 2298-36-4 4-aminophenoxyacetic acid 
• 20142-88-5 2-(4-nitrophenoxy)acetyl chloride 
• 63218-14-4 4-nitrophenoxyacetamide 
• 39149-13-8 p-N-acetylaminophenoxyacetic acid 
• 17716-80-2 2-(4-nitrophenoxy)-N-phenylacetamide 
• 443902-49-6 3'-Nitro-<2-(4-nitrophenoxy)>acetanilid 
• 106272-93-9 (4-nitro-phenoxy)-acetic acid cyclohexyl ester 
• 100726-03-2 (4-nitro-phenoxy)-acetic acid phenyl ester 
• 50508-33-3 1-(morpholin-4-yl)-2-(4-nitrophenoxy)ethanone 
• 100537-61-9 2-((4-nitrophenoxy)methyl)benzothiazole 
• 105377-54-6 (4-Nitro-phenoxy)-acetic acid; compound with 2-[bis-(2-hydroxy-ethyl)-amino]-ethanol 
• 1445-36-9 N-phenylamidophosphoric acid 
• 52547-52-1 N-(2-hydroxyethyl)-2-(4-nitrophenoxy)acetamide 

Relevant academic research and scientific papers

Application of magnetic Fe3O4 nanoparticles as a reusable heterogeneous catalyst in the synthesis of β-lactams containing amino groups

Herein we report the catalytic activity of magnetic Fe3O4 nanoparticles to promote the reduction of β-lactams containing nitroaryl groups to β-lactams containing aminoaryl groups in ethanol. The catalytic experimental conditions have

Design and synthesis of α-phenoxy-N-sulfonylphenyl acetamides as Trypanosoma brucei Leucyl-tRNA synthetase inhibitors

Human African trypanosomiasis (HAT), caused by the parasitic protozoa Trypanosoma brucei, is one of the fatal diseases in tropical areas and current medicines are insufficient. Thus, development of new drugs for HAT is urgently needed. Leucyl-tRNA synthetase (LeuRS), a recently clinically validated antimicrobial target, is an attractive target for development of antitrypanosomal drugs. In this work, we report a series of α-phenoxy-N-sulfonylphenyl acetamides as T. brucei LeuRS inhibitors. The most potent compound 28g showed an IC50 of 0.70 μM which was 250-fold more potent than the starting hit compound 1. The structure-activity relationship was also discussed. These acetamides provided a new scaffold and lead compounds for the further development of clinically useful antitrypanosomal agents.

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

A series of aryloxyacetic acid derivatives were designed and synthesized as 4-hydoxyphenylpyruvate dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (Ki = 0.011 μM) and I23 (Ki = 0.012 μM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (Ki = 0.013 μM). Furthermore, the newly synthesized compounds show significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, II4 exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification.

Structure-based modification of carbonyl-diphenylpyrimidines (Car-DPPYs) as a novel focal adhesion kinase (FAK) inhibitor against various stubborn cancer cells

A family of carbonyl-substituted diphenylpyrimidine derivatives (Car-DPPYs) with strong activity against focal adhesion kinase (FAK), were described in this manuscript. Among them, compounds 7a (IC50 = 5.17 nM) and 7f (IC50 = 2.58 nM) displayed equal anti-FAK enzymatic activity to the lead compound TAE226 (6.79 nM). In particular, compound 7a also exhibited strong antiproliferative activity against several stubborn cancer cells, including AsPC-1 cells (IC50 = 0.105 μM), BxPC-3 cells (IC50 = 0.090 μM), and MCF-7/ADR cells (IC50 = 0.59 μM). Additionally, compound 7a also showed great antitumor efficacy in vivo via aAsPC-1 cancer Xenograft mouse model. The preliminary mechanism study by Western blot analysis revealed that 7a repressed FAK phosphorylation in AsPC cancer cells. Taken together, the results indicate that compound 7a may serve as a promising preclinical candidate for treatment of stubborn cancers.

Ketoreductase catalyzed stereoselective bioreduction of α-nitro ketones

We report here the stereoselective bioreduction of α-nitro ketones catalyzed by ketoreductases (KREDs) with publicly known sequences. YGL039w and RasADH/SyADH were able to reduce 23 class I substrates (1-aryl-2-nitro-1-ethanone (1)) and ten class II substrates (1-aryloxy-3-nitro-2-propanone (4)) to furnish both enantiomers of the corresponding β-nitro alcohols, with good-to-excellent conversions (up to >99%) and enantioselectivities (up to >99% ee) being achieved in most cases. To the best of our knowledge, KRED-mediated reduction of class II α-nitro ketones (1-aryloxy-3-nitro-2-propanone (4)) is unprecedented. Select β-nitro alcohols, including the synthetic intermediates of bioactive molecules (R)-tembamide, (S)-tembamide, (S)-moprolol, (S)-toliprolol and (S)-propanolol, were stereoselectively synthesized in preparative scale with 42% to 90% isolated yields, showcasing the practical potential of our developed system in organic synthesis. Finally, the advantage of using KREDs with known sequence was demonstrated by whole-cell catalysis, in which β-nitro alcohol (R)-2k, the key synthetic intermediate of hypoglycemic natural product (R)-tembamide, was produced in a space-time yield of 178 g L?1 d?1 as well as 95% ee by employing the whole cells of a recombinant E. coli strain coexpressing RasADH and glucose dehydrogenase as the biocatalyst.

Novel pyrazolone derivatives and corresponding europium(III) complexes: Synthesis and properties research

A series of pyrazolone derivatives ligands L1?7 were successfully synthesized and validated by 1H NMR and MS, corresponding europium complexes [EuL1?7(NO3)2]NO3·EtOAc were synthesized. Physico-chemistry properties of title complexes were determined by Elemental analysis, Molar conductance, UV absorption spectra, IR spectra and Thermogravimetric analysis. The title complexes exhibit characteristic red fluorescence of Eu3+. The effect of various substituent groups in ligands on the of title Eu3+ complexes is ordered: Cl > -Br > -OCH3 > -F > -CH3 > -H > -NO2, and [EuL6(NO3)2]NO3·EtOAc containing Cl possesses the strongest fluorescence intensity, so does fluorescence quantum yield. The electrochemical properties indicate that energy gap Eg and LUMO energy level are huge affected by substituent groups, and variation trends of LUMO energy level affected by diverse substituent groups are also different. The prepared title europium complexes have potential application prospects in the fields of photoelectric functional materials and life sciences.

Synthesis and luminescence properties of novel 8-hydroxyquinoline derivatives and their Eu(III) complexes

Six novel 8-hydroxyquinoline derivatives were synthesized using 2-methyl-8-hydroxyquinoline and para-substituted phenol as the main starting materials, and were characterized by 1H nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV) light analysis and infra-red (IR) light analysis. Their complexes with Eu(III) were also prepared and characterized by elemental analysis, molar conductivity, UV light analysis, IR light analysis, and thermogravimetric–differential thermal analysis (TG–DTA). The results showed that the ligand coordinated well with Eu(III) ions and had excellent thermal stability. The structure of the target complex was EuY1–6(NO3)3.2H2O. The luminescence properties of the target complexes were investigated, the results indicated that all target complexes had favorable luminescence properties and that the introduction of an electron-donating group could enhance the luminescence intensity of the corresponding complexes, but the addition of an electron-withdrawing group had the opposite effect. Among all the target complexes, the methoxy-substituted complex (–OCH3) had the highest fluorescence intensity and the nitro-substituted complex (–NO2) had the weakest fluorescence intensity. The results showed that 8-hydroxyquinoline derivatives had good energy transfer efficiency for the Eu(III) ion. All the target complexes had a relatively high fluorescence quantum yield. The fluorescence quantum yield of the complex EuY3(NO3)3.2H2O was highest among all target complexes and was up to 0.628. Because of excellent luminescence properties and thermal stabilities of the Eu(III) complexes, they could be used as promising candidate luminescent materials.

Identification of highly potent BTK and JAK3 dual inhibitors with improved activity for the treatment of B-cell lymphoma

The BTK and JAK3 receptor tyrosine kinases are two validated and therapeutically amenable targets in the treatment of B-cell lymphomas. Here we report the identification of several classes of pyrimidine derivatives as potent BTK and JAK3 dual inhibitors.

Purine compounds, composition and application

The invention belongs to the technical field of medicine and relates to purine compounds, composition and an application of the composition. The compounds represented as a general formula (I) as well as all possible isomers, pharmaceutical salts or hydrates or the composition of the compounds are used for treating diseases caused by BTK (Bruton tyrosine kinase) and particularly used for treating diffuse large B cell lymphoma, follicular lymphoma or chronic lymphocytic leukemia.

Methyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism

Previously, we reported a hypoxia-inducible factor (HIF)-1 inhibitor LW6 containing an (aryloxyacetylamino)benzoic acid moiety inhibits malate dehydrogenase 2 (MDH2) using a chemical biology approach. Structure-activity relationship studies on a series of (aryloxyacetylamino)benzoic acids identified selective MDH1, MDH2, and dual inhibitors, which were used to study the relationship between MDH enzyme activity and HIF-1 inhibition. We hypothesized that dual inhibition of MDH1 and MDH2 might be a powerful approach to target cancer metabolism and selected methyl-3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)-benzoate (16c) as the most potent dual inhibitor. Kinetic studies revealed that compound 16c competitively inhibited MDH1 and MDH2. Compound 16c inhibited mitochondrial respiration and hypoxia-induced HIF-1α accumulation. In xenograft assays using HCT116 cells, compound 16c demonstrated significant in vivo antitumor efficacy. This finding provides concrete evidence that inhibition of both MDH1 and MDH2 may provide a valuable platform for developing novel therapeutics that target cancer metabolism and tumor growth.