704-14-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxy-2-nitrophenol is used as a reagent in the synthesis of conformationally constrained spirocycles, which are employed as CCR1 antagonists. These antagonists are important in the development of drugs targeting inflammatory and immune response disorders.
Additionally, 5-Methoxy-2-nitrophenol is used in the preparation of phenylsulfonyl aminophenoxybenzoates, which serve as EP1 receptor antagonists. These antagonists have potential applications in the treatment of pain and inflammation by modulating the prostaglandin E2 signaling pathway.

InChI:InChI=1/C7H7NO4/c1-12-5-2-3-6(8(10)11)7(9)4-5/h2-4,9H,1H3

Upstream product

• 150-19-6 O-methylresorcine 
• 6627-53-8 1-chloro-3-methoxy-4-nitrobenzene 
• 124-41-4 sodium methylate 
• 5451-83-2 acetic acid 3-methoxyphenyl ester 
• 67764-33-4 cyclopentyl nitrite 
• 20278-59-5 4,5-dinitro-2-methoxyaniline 
• 64-19-7 acetic acid 
• 3163-07-3 4-nitroresorcinol 
• 77-78-1 dimethyl sulfate 
• 28987-59-9 3-chloro-4-nitroanisole 
• 100-17-4 para-methoxynitrobenzene 
• 7664-93-9 sulfuric acid 
• 60-29-7 diethyl ether 
• 7697-37-2 nitric acid 

Downstream Products

• 107920-76-3 2-(benzyloxy)-4-methoxy-1-nitrobenzene 
• 4920-84-7 2,4-dimethoxynitrobenzene 
• 40925-70-0 2-amino-5-methoxyphenol 
• 131761-75-6 (5-Methoxy-2-nitro-phenoxy)-acetic acid methyl ester 
• 1141-87-3 2-(3-Dimethylamino-propoxy)-4-methoxy-anilin 
• 1026806-90-5 Methoxymethoxy-(5-methoxy-2-nitro-phenoxy)-acetic acid isopropyl ester 
• 51652-35-8 5-methoxy-2,4-dinitrophenol 
• 633357-97-8 4-bromo-5-methoxy-2-nitro-phenol 
• 757232-66-9 2,4-dibromo-3-methoxy-6-nitro-phenol 
• 23999-64-6 6-methoxy-2-methyl-benzoxazole 
• 157067-43-1 ethyl 5-methoxy-2-nitrophenoxyacetate 
• 3934-97-2 4-methoxycatechol 
• 778599-56-7 1-bromo-2,4-dimethoxy-5-nitrobenzene 
• 99179-70-1 2-Acetoxy-4-methoxy-phenol 

Relevant academic research and scientific papers

Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation

The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.

Design and synthesis of novel benzoxazole analogs as Aurora B kinase inhibitors

A novel series of benzoxazole analogs was designed and synthesized, and their inhibitory activities against Aurora kinases were evaluated. Some of the tested compounds exhibited a promising activity with respect to the inhibition of Aurora B kinase. A structure-activity relationship study indicated that linker length, regiochemistry, and halogen substitution play important roles in kinase inhibitory potency. The binding modes between representative compounds and Aurora kinases were interpreted through a molecular docking study to explain the inhibitory activity and selectivity for Aurora A and B kinases. Compounds 13l and 13q also show an antiproliferative effect on the human tumor cell lines in a dose-dependent manner. The most potent 13q demonstrated good efficacy in the prostate cancer PC-3 tumor xenograft model.

Improved Protocol for Mononitration of Phenols with Bismuth(III) and Iron(III) Nitrates

A simple and efficient multigram procedure was developed for the selective mononitration of various activated phenols. The reaction proceeded smoothly with 0.5 equivalents of Bi(NO3)3 · 5H2O or Fe(NO3)3 · 9H2O in acetone at ambient temperature or at reflux. The desired products were isolated in 62-93% total yield and essentially no overnitrated compounds were detected.

Biomimetic synthesis of isoindolinones related to the marilines

The non-enzymatic formation of the racemic isoindolinone core structure during the biosynthesis of the marine natural products mariline A and B was mimicked by employing structurally closely related model substrates. Thus, condensation of 2-formyl-3,5-dim

Analgesic Compounds, Compositions, and Uses Thereof

The invention relates to compounds, compositions, and methods for diminishing pain in a subject in need thereof comprising administering the compounds and compositions herein described.

Nitro-group-directed selective dealkylation

Nitro-substituted phenolic ethers were successfully selectively dealkylated. The directing effect of the nitro group is supported by the excellent regioselectivities and good yields. These reactions demonstrate that the complexation of AlCl3 with the phenolic nitro group is stronger than with the phenolic ether alone. The mechanism for the selective dealkylation directed by the nitro group is proposed.

Completion of the spectroscopical data for the synthesis of DIMBOA

Cyclic hydroxamic acids like 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin- 3(4H)-one (DIMBOA) and 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA) are found in several plants playing an important role in the defense-system of plants against a variety of enemies. To investigate new mechanism and effects we synthesized the molecules using known synthetic pathways. Since the chemical data of DIMBOA are not complete or even false, we decided to publish the missing ones in this journal. O?sterreichische Apotheker-Verlagsgesellschaft m. b. H.

2-CARBOXAMIDE-BENZIMIDAZOLES USEFUL IN THE TREATMENT AND PREVENTION OF ISCHEMIC REPERFUSION INJURY

The subject invention relates to compounds having the structure: (I) wherein: (a) R1 is selected from the group consisting of alkyl, aryl, alkoxy, and aryloxy, the alkyl and aryl portions of preferred R1 having from 1 to about 14 carbon atoms; (b) R3 and R4 are independently selected from the group consisting of hydrogen, halo, alkyl, alkoxy, alkyl-aryloxy, alkylthio, amino, and mono- or dialkylaminio, the alkyl portions of preferred R3 and R4 having from 1 to about 8 carbon atoms; except that R3 and R4 are not both hydrogen; (c) each R5 is independently selected from the group consisting of hydrogen, halo, cyano, alkyl, hydroxy, alkoxy, thio, alkylthio, amino, and mono- or dialkylamino, the alkyl portions of preferred R5 having from 1 to about 8 carbon atoms. The subject invention further relates to compositions comprising these compound. The subject compounds are useful for preventing or treating reperfusion injury of a variety of tissues.

Substituted pyrazinones, pyridines and pyrimidines as corticotropin releasing factor ligands

Compounds provided herein are novel substituted pyrazinones, pyridines and pyrimidines of Formula (I) and (II): Such compounds are particularly useful as CRF receptor ligands, and hence, in the treatment of various neurologically-related disorders such as affective disorder, anxiety and depression.

The nitration of electron-rich aromatics

The successful mononitration of a variety of electron-rich aromatic substrates is reported, employing either nitronium tetrafluoroborate or 'claycop' as the nitrating agent. Dinitration of four of the substrates was achieved when employing nitronium tetrafluoroborate. Several of the products have previously been prepared only by indirect methods.