99-42-3

Usage

Uses

Used in Chemical Synthesis:
Benzoic acid, 4-hydroxy-3-nitro-, methyl ester is used as a key intermediate in the synthesis of various organic compounds, particularly in the production of 4-alkoxy-3-nitrobenzoic acids. It serves as a starting material for the alkylation process, where it reacts with corresponding n-alkylbromides in 3-pentanone to yield the desired 4-alkoxy-3-nitrobenzoic acid derivatives.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzoic acid, 4-hydroxy-3-nitro-, methyl ester can be utilized as a building block for the development of new drugs with potential therapeutic applications. Its unique chemical structure allows for the creation of novel compounds with specific biological activities, which can be further optimized for their efficacy and safety.
Used in Research and Development:
Benzoic acid, 4-hydroxy-3-nitro-, methyl ester is also used in research and development settings to study the properties and reactivity of various functional groups present in its structure. This knowledge can be applied to design new synthetic routes and develop innovative applications for Benzoic acid,4-hydroxy-3-nitro-, methyl ester and its derivatives.

InChI:InChI=1/C8H7NO5/c1-14-8(11)5-2-3-7(10)6(4-5)9(12)13/h2-4,10H,1H3/p-1

Upstream product

• 67-56-1 methanol 
• 616-82-0 3-nitro-4-hydroxybenzoic acid 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 144-55-8 sodium hydrogencarbonate 
• 7664-93-9 sulfuric acid 
• 107-06-2 1,2-dichloro-ethane 

Downstream Products

• 31582-81-7 1-(4-methoxycarbonyl-2-nitro-phenyl)-pyridinium; toluene-4-sulfonate 
• 59691-12-2 methyl 3-nitro-4-propoxybenzoate 
• 31600-19-8 3-nitro-4-(toluene-4-sulfonyloxy)-benzoic acid methyl ester 
• 56388-02-4 methyl 2-aminobenzo[d]oxazole-5-carboxylate 
• 89563-19-9 4-methoxycarbonyl-2-nitro-6-phenyliodoniophenolate 
• 193965-90-1 3-Nitro-4-(2-pyrrolidin-1-yl-ethoxy)-benzoic acid methyl ester 
• 123027-96-3 3-nitro-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester 
• 136663-21-3 methyl 2-methyl-1,3-benzoxazole-5-carboxylate 
• 536-25-4 methyl 3-amino-4-hydroxybenzoate 
• 62448-60-6 N-cyclohexyl-2-hydroxy-2-phenylethanamide 
• 191096-34-1 dihydro-3-(4-carbomethoxy-2-nitrophenoxy)-2(3H)-furanone 

Relevant academic research and scientific papers

Photochemical Nitration of Benzoic Acid Derivatives by Irradiation to Nitrate Ions

Photochemical nitration of p-hydroxybenzoate, HBA, initiated by UV irradiation to sodium nitrate or sodium nitrite was observed in aqueous solutions. 4-Hydroxy-3-nitrobenzoate was formed, with maximum quantum yields of 0.007 and 0.09 for NaNO3 and NaNO2, respectively.From the dependence of the yields on the pH and concentrations of oxygen and OH-scavengers, we propose a mechanism involving the addition of OH(radical) to the aromatic ring of HBA and electron abstraction from NO2 by the OH(radical) adduct for the photonitration.

Synthesis, Structure Revision, and Cytotoxicity of Nocarbenzoxazole G

The total synthesis of nocarbenzoxazoles F (1) and G (2), originally obtained from the marine-derived halophilic bacterial strain Nocardiopsis lucentensis DSM 44048, was achieved via a simple and versatile route involving microwave-assisted construction of a benzoxazole skeleton, followed by carbon-carbon bond formation with the corresponding aryl bromides. Unfortunately, the 1H and 13C NMR spectra of natural nocarbenzoxazole G did not agree with those of the synthesized compound. In particular, the spectra of the isolated and synthesized compounds showed considerable differences in the signals from the protons and carbons in the aryl group. The revised structure was validated by the total synthesis of the actual nocarbenzoxazole G (8c) molecule, which is a regioisomer of the compound that was reported earlier as nocarbenzoxazole G. The synthesized derivatives showed specific cytotoxicity to the human cervical carcinoma cell line, HeLa, but did not have any remarkable effect on the other cell lines.

N-(3-nitro-4-alkoxybenzoyl)amino acid compounds as well as preparation method and application thereof

The invention discloses N-(3-nitro-4-alkoxybenzoyl)amino acid compounds as well as a preparation method and an application thereof and belongs to the field of medicines. 4-hydroxy-3-nitrobenzoic acidis subjected to methanol esterification, bromo-alkane substitution, hydrolysis and chlorination and then acylated with L-phenylglycine, R2 which is L-phenylglycine sodium salt is obtained, and the N-(3-nitro-4-alkoxybenzoyl)amino acid compounds are obtained after hydrolysis. The N-(3-nitro-4-alkoxybenzoyl)amino acid compounds have novel chemical structures, have good effects in an in-vitro xanthine oxidase inhibition activity test and can be used for treating and preventing gout diseases.

Nitration method for aryl phenol or aryl ether derivative

The invention relates to a nitration method for an aryl phenol or aryl ether derivative. The method comprises the steps of stirring an aryl phenol or aryl ether compound, nitrate, trimethylchlorosilane (TMSCl) and a copper salt in an acetonitrile solution in air at room temperature, simultaneously, monitoring extent of reaction through a TLC dot plate, removing a solvent from a mixture by a rotaryevaporator after a substrate is consumed completely, and carrying out purification through a silica-gel column, thereby obtaining a nitroolefin derivative. Meanwhile, the selective mono-nitration orbis-nitration of the substrate can be achieved through controlling equivalent weight of the nitrate. Compared with the prior art, the nitration method disclosed by the invention has the advantages that the consumption of strong-acid substances is avoided, the reaction conditions are mild, the yield is high, the applicable range of the substrate is wide, reaction activity is free of obvious attenuation after an amplified reaction, and an excellent yield is still obtained, so that the method has an obvious industrial application value.

QUINAZOLINE HETEROCYCLIC COMPOUND AS EGFR KINASE INHIBITOR AND PREPARATION AND APPLICATION THEREOF

The present invention relates to an N-substituted-phenyl-5-substituted-alkoxy-2,3-dihydro-[1,4]dioxane[2,3-f]quinazolin-10-amine (I) or 4-substituted-arylamino-6-substituted-alkyl-6H-[1,4]oxazino[3,2-g]quinazoline-7(8H)-one (II) type compounds, a preparation method thereof and an application thereof as an inhibitor for epidermal growth factor receptor (EGFR) (comprising some mutant forms of EGFR) to treat cancer. These compounds and salts thereof can be used to treat or prevent various cancer diseases.

2 - (methylthio) benzo [d] oxazole-5-carboxylic acid and its use

The invention discloses a 2-(methylthio)benzo[d]oxazolyl-5-carboxylic acid and application thereof. The product is prepared by the following steps: synthesizing methyl 3-nitro-4-hydroxybenzoate; synthesizing 3-amino-4-hydroxybenzoic acid; synthesizing 2-sulfhydrylbenzo[d]oxazolyl-5-carboxylic acid; and synthesizing the 2-(methylthio)benzo[d]oxazolyl-5-carboxylic acid. The test result indicates that the electrochemiluminescence property of the 2-(methylthio)benzo[d]oxazolyl-5-carboxylic acid is very stable within the potential range of (-2-0)V and has obviously higher luminescent intensity in a water phase than an organic phase.

Novel morpholin-3-one fused quinazoline derivatives as EGFR tyrosine kinase inhibitors

A series of novel morpholin-3-one-fused quinazoline derivatives were designed, synthesized and evaluated as EGFR tyrosine kinase inhibitors. Nineteen compounds showed significant inhibitory activities against EGFRwtkinase (IC50?wt(IC50?=?53.1?nM). Compound a7 and a8 showed excellent inhibitory activities against mutant EGFRT790M/L858Rand strong antiproliferative activity against H358 and A549 cell lines. Finally, molecular docking studies were performed to predict the possible binding mode of the target compounds. It is believed that this work would be very useful for designing a new series of tyrosine kinase inhibitors targeting EGFR.

Regioselective nitration of phenols and phenyl ethers using aluminium nitrate on silica as a nitrating system

Silica supported aluminum nitrate (Al(NO3)3·9H2O) was found to be an excellent reagent for the nitration of phenols and phenyl ethers. This procedure works efficiently on most of the examples at room temperature yielding nitro derivatives in fair to good yields with high regioselectivity. The present methodology evidenced a considerable enhancement in the reaction rate along with high o-selectivity, excellent yields, ease of handling and the simplicity in work up.

Synthesis and structure-activity relationship study of chemical probes as hypoxia induced factor-1α/malate dehydrogenase 2 inhibitors

A structure-activity relationship study of hypoxia inducible factor-1α inhibitor 3-aminobenzoic acid-based chemical probes, which were previously identified to bind to mitochondrial malate dehydrogenase 2, was performed to provide a better understanding of the pharmacological effects of LW6 and its relation to hypoxia inducible factor-1α (HIF-1α) and malate dehydrogenase 2 (MDH2). A variety of multifunctional probes including the benzophenone or the trifluoromethyl diazirine for photoaffinity labeling and click reaction were prepared and evaluated for their biological activity using a cell-based HRE-luciferase assay as well as a MDH2 assay in human colorectal cancer HCT116 cells. Among them, the diazirine probe 4a showed strong inhibitory activity against both HIF-1α and MDH2. Significantly, the inhibitory effect of the probes on HIF-1α activity was consistent with that of the MDH2 enzyme assay, which was further confirmed by the effect on in vitro binding activity to recombinant human MDH2, oxygen consumption, ATP production, and AMP activated protein kinase (AMPK) activation. Competitive binding modes of LW6 and probe 4a to MDH2 were also demonstrated.

Synthesis and biological evaluation of ortho-carborane containing benzoxazole as an inhibitor of hypoxia inducible factor (HIF)-1 transcriptional activity

ortho-Carborane and adamantane containing benzoxazoles were synthesized by intramolecular dehydration of the corresponding phenoxyacetanilides. Among the compounds synthesized, ortho-carborane containing benzoxazole 2b which has a carboxylic group on the benzoxazole ring, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity with the IC50 value of 14.4 μM toward HeLa cell-based reporter gene assay.