4900-66-7

Usage

Uses

Used in Organic Chemistry:
2-methoxy-1-nitronaphthalene is used as a precursor for the synthesis of various organic compounds. Its unique structure with a methoxy and nitro group allows for versatile chemical reactions, making it a valuable intermediate in the production of a range of organic molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-methoxy-1-nitronaphthalene is utilized as a starting material for the development of new drugs. Its chemical properties enable the creation of novel pharmaceutical products with potential therapeutic applications.
Used in Environmental Protection:
Although 2-methoxy-1-nitronaphthalene can be harmful to the environment, it is also used in the development of methods to detect and mitigate its environmental impact. This includes the creation of technologies and strategies to prevent its release into water and soil, as well as to remediate contaminated sites.

InChI:InChI=1/C11H9NO3/c1-15-10-7-6-8-4-2-3-5-9(8)11(10)12(13)14/h2-7H,1H3

Upstream product

• 93-04-9 2-Methoxynaphthalene 
• 64-19-7 acetic acid 
• 7697-37-2 nitric acid 
• 5392-12-1 2-methoxy-1-naphthaldehyde 
• 56-23-5 tetrachloromethane 
• 550-60-7 1-nitro-2-naphthol 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 88-75-5 2-hydroxynitrobenzene 
• 67-56-1 methanol 
• 342-64-3 2-fluoro-1-nitro-naphthalene 
• 323-09-1 2-fluoronaphthalene 

Downstream Products

• 4920-80-3 3-methoxy-2-nitrobenzoic acid 
• 98589-66-3 4-methoxy-3-nitro-phthalic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 69745-41-1 1-Nitro-2-methoxy-4-(2-phenylethyl)-naphthalen 
• 2246-42-6 2-methoxynaphthylamine 
• 1547162-41-3 5-hydroxypomalidomide 
• 1572936-74-3 2-(2-methoxynaphthalen-1-ylamino)-5-nitrobenzoic acid 
• 103369-02-4 2-(3-methoxy-4-nitronaphthyl)-1-phenylethanol 
• 26207-06-7 4-methylnaphthalen-2-ol 
• 123856-15-5 5-nitro-6-methoxy-2-bromonaphthalene 
• 606-57-5 1-nitro-2-naphthylamine 
• 550-60-7 1-nitro-2-naphthol 
• 69745-38-6 1-Nitro-2-methoxy-4-(2-phenylethyl)-3,4-dihydronaphthalen 
• 91786-78-6 4-Benzyl-2-methoxy-1-nitro-1,4-dihydro-naphthalene 

Relevant academic research and scientific papers

ION CHANNEL ANTAGONISTS/BLOCKERS AND USES THEREOF

Provided are ion channel antagonists/blockers and uses thereof. Specifically, it provides the compounds of formula (I) or pharmaceutically acceptable salts, stereoisomers, solvates or prodrugs, preparation method therefor and application thereof. Definition of each group in the formula can be found in the specification for details. Provided is also pharmaceutical composition useful for treatment of heart disease and other ion channel related diseases.

PYRIDONE-PYRIMIDINE DERIVATIVE ACTING AS KRASG12C MUTEIN INHIBITOR

Provided are a class of KRAS G12C mutein inhibitors, which relate in particular to a compound represented by formula (I), an isomer thereof, and a pharmaceutically acceptable salt thereof.

Method for catalyzing selective nitrification of 2-methoxynaphthalene by utilizing zeolite molecular sieve

The invention discloses a method for catalyzing selective nitrification of 2-methoxynaphthalene by utilizing a zeolite molecular sieve. The method comprises the following steps: S1, dissolving 6 mmolof 2-methoxynaphthalene in 10 mL of dichloromethane, adding 5 mL of acetic anhydride and 0.3-1.1 g of the zeolite molecular sieve catalyst, slowly adding 2 mmol of aluminum nitrate in a stirring state, and carrying out a water bath stirring reaction at 25 DEG C for 12 h; S2, hydrolyzing acetic anhydride at 40 DEG C for 1 h after the reaction is finished; S3, extracting, washing and drying the reacted solution obtained in step S2 after THE hydrolysis is completed; and S4, performing rotary evaporation on the dichloromethane in a solution product obtained in step S3 to achieve evaporative crystallization in order to obtain a crude extract, wherein the raw material conversion rate reaches 85.20-100%, the yield reaches 69.88-82.02%, and the isomerization rate reaches 1.56-6.09. The zeolite molecular sieve is used for catalyzing the selective nitration reaction of 2-methoxynaphthalene for the first time, the catalytic effect of the ZSM-5 zeolite molecular sieve is the most remarkable, and when the weight of the ZSM-5 catalyst is 0.9 g, the substrate conversion rate is high and reaches 93.98%, the yield is 77.09%, and the isomerization rate reaches 6.05%.

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.

Direct nitration method of electron-enriched aromatic hydrocarbons

The invention discloses a direct nitration method of electron-enriched aromatic hydrocarbons, and belongs to the field of organic synthesis. The direct nitration method is a novel green free radical nitration method; aromatic hydrocarbons are taken as raw materials, acetonitrile, dichloromethane, chloroform, or acetone is taken as a reaction solvent, at room temperature conditions, the raw materials and green nitration reagent tert-butyl nitrite (TBN) are subjected to free radical nitration so as to obtain nitro-aromatic compounds. According to the direct nitration method, no metal is adoptedin reaction, tert-butyl nitrite is directly adopted in nitration reaction. Electron-donating groups such as OMe are introduced, the electron density of aromatic compounds is increased, the nitration reaction possibility is increased. The using amount of tert-butyl nitrite is reduced; only a product and tert-butyl alcohol are generated, environment pollution is reduced. The direct nitration methodis promising in application prospect in the field of nitro-aromatic compound synthesis, green nitration is realized, and a novel idea is provided for large-scale industrialized nitro-aromatic compoundproduction.

Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution

In view of the few reports concerning aromatic nucleophilic substitution reactions featuring an alkoxy group as a leaving group, the aromatic nucleophilic substitution of 2,4-dimethoxy-nitrobenzene was investigated with a bulky t-butoxide nucleophile under microwave irradiation. The transetherification of 2,4-dimethoxynitrobenezene with sodium t-butoxide under specific conditions, namely for 20 min at 110C in 10% dimethoxyethane in toluene, afforded the desired product in 87% yield with exclusive ortho-selectivity. A variety of reaction conditions were screened to obtain the maximum yield. The aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene with t-butoxide should be carried out under controlled conditions in order to avoid the formation of byproducts, unlike that of dihalogenated activated ben-zenes. Among the formed byproducts, a major compound was elucidated as 2,4-dimethoxy-N-(5-methoxy-2-nitrophenyl)aniline by X-ray crystallography.

TOLL-LIKE RECEPTOR AGONISTS

Compounds described herein can be used for therapeutic purposes. The compounds can be TLR agonists, such as TLR7 or TLR8 agonists. The compounds can be included in pharmaceutical compositions and used for therapies were being a TLR agonist is useful. The pharmaceutical compositions can include any ingredients, such as carries, diluents, excipients, fillers or the like that are common in pharmaceutical compositions. The compounds can be those illustrated or described herein as well as derivatives thereof, prodrugs thereof, salts thereof, or stereoisomers thereof, or having any chirality at any chiral center, or tautomer, polymorph, solvate, or combinations thereof. As such, the compounds can be used as adjuvants in vaccines, as well as for other therapeutic purposes described herein.

Human toll-like receptor 8-selective agonistic activities in 1-alkyl-1 h -benzimidazol-2-amines

Toll-like receptor (TLR)-8 agonists strongly induce the production of T helper 1-polarizing cytokines and may therefore serve as promising candidate vaccine adjuvants, especially for the very young and the elderly. Earlier structure-based ligand design led to the identification of 3-pentyl-quinoline-2-amine as a novel, human TLR8-specific agonist. Comprehensive structure-activity relationships in ring-contracted 1-alkyl-1H-benzimidazol-2-amines were undertaken, and the best-in-class compound, 4-methyl-1-pentyl-1H-benzo[d]imidazol-2-amine, was found to be a pure TLR8 agonist, evoking strong proinflammatory cytokine and Type II interferon responses in human PBMCs, with no attendant CD69 upregulation in natural lymphocytic subsets. The 1-alkyl-1H-benzimidazol-2-amines represent a novel, alternate chemotype with pure TLR8-agonistic activities and will likely prove useful not only in understanding TLR8 signaling but also perhaps as a candidate vaccine adjuvant.

PROCESSES FOR PREPARING ISOINDOLINE-1,3-DIONE COMPOUNDS

Provided herein are processes for preparing an isoindoline- 1.3-dione compound, or an enantiomer or a mixture of enantiomers thereof; or a pharmaceutically acceptable salt, solvate, hydrate, or polymorph thereof.

Monna, a potent and selective blocker for transmembrane protein with unknown function 16/anoctamin-1

Transmembrane protein with unknown function 16/anoctamin-1 (ANO1) is a protein widely expressed in mammalian tissues, and it has the properties of the classic calcium-activated chloride channel (CaCC). This protein has been implicated in numerous major physiological functions. However, the lack of effective and selective blockers has hindered a detailed study of the physiological functions of this channel. In this study, we have developed a potent and selective blocker for endogenous ANO1 in Xenopus laevis oocytes (xANO1) using a drug screening method we previously established (Oh et al., 2008). We have synthesized a number of anthranilic acid derivatives and have determined the correlation between biological activity and the nature and position of substituents in these derived compounds. A structure-activity relationship revealed novel chemical classes of xANO1 blockers. The derivatives contain a-NO2 group on position 5 of a naphthyl group-substituted anthranilic acid, and they fully blocked xANO1 chloride currents with an IC 5050 of 0.08 μM for xANO1. Selectivity tests revealed that other chloride channels such as bestrophin-1, chloride channel protein 2, and cystic fibrosis transmembrane conductance regulator were not appreciably blocked by 10～30 μM MONNA. The potent and selective blockers for ANO1 identified here should permit pharmacological dissection of ANO1/CaCC function and serve as potential candidates for drug therapy of related diseases such as hypertension, cystic fibrosis, bronchitis, asthma, and hyperalgesia.