52827-01-7

Usage

Uses

Used in Research and Laboratory Settings:
[(4-methoxyphenyl)(nitroso)amino]acetic acid is used as a research compound for its unique structure and potential applications in medicinal chemistry and drug development. Its presence in the field of organic chemistry makes it an interesting subject for further investigation.
Used in Medicinal Chemistry:
In the medicinal chemistry industry, [(4-methoxyphenyl)(nitroso)amino]acetic acid is used as a building block for the synthesis of various pharmaceutical compounds. Its distinct functional groups, including the nitroso and 4-methoxyphenyl groups, allow for the creation of novel molecules with potential therapeutic properties.
Used in Drug Development:
Within the drug development sector, [(4-methoxyphenyl)(nitroso)amino]acetic acid serves as a key component in the design and synthesis of new drugs. Its unique structure may contribute to the development of innovative therapeutic agents, particularly in the areas of targeted drug delivery and novel pharmacological approaches.

Upstream product

• 22094-69-5 N-(4-methoxyphenyl)glycine 
• 104-94-9 4-methoxy-aniline 
• 50845-77-7 N-(4-methoxy)phenylglycine ethyl ester 

Downstream Products

• 5020-93-9 4-bromo-3-(p-methoxyphenyl)sydnone 
• 1394248-95-3 3-[1-(4-isobutylphenyl)ethyl]-4-[3-(p-anisyl)-4-sydnonylidene]amino-5-mercapto-1,2,4-triazole 
• 1394249-05-8 1-morpholinomethyl-3-[1-(4-isobutylphenyl)ethyl]-4-[3-(p-anisyl)-4-sydnonylidene]amino-1,2,4-triazol-5-thione 
• 1394249-06-9 1-piperidinomethyl-3-[1-(4-isobutylphenyl)ethyl]-4-[3-(p-anisyl)-4-sydnonylidene]amino-1,2,4-triazol-5-thione 
• 1394249-07-0 1-N-methyl-piperazinomethyl-3-[1-(4-isobutylphenyl)ethyl]-4-[3-(p-anisyl)-4-sydnonylidene]amino-1,2,4-triazol-5-thione 
• 14484-84-5 3-(4-methoxyphenyl)-4-formylsydnone 

Relevant academic research and scientific papers

Novel sydnone derivatives carrying azidomethyl-1,2, 4-oxadiazole unit and their 1,3-dipolar cycloadditions

A series of 1,2,4-oxadiazolymethyl sydnones carrying azido group were synthesized and subjected to react with a variety of alkenic and acetylenic dipolarophilic reagents; N-phenyl maleimide, phenyl vinyl sulfone, and phenyl propiolic acid. All the new products are identified by spectral/physical data including high-resolution mass measurements and X-ray diffraction data.

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.

One-pot synthesis of 1,4-disubstituted pyrazoles from arylglycines via copper-catalyzed sydnone-alkyne cycloaddition reaction

A robust method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone-alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step one-pot procedure.

Synthesis, characterization, and antimicrobial screening of some Mannich base sydnone derivatives

The title compounds (5a-j), (6a-j), and (7a-j) were prepared via a four-step procedure using starting material 4-methoxyaniline (1). The structure of all synthesized compounds was confirmed by FT-IR, 1H NMR, 13C NMR, and CHN analysis. The synthesized compounds were tested for their antibacterial and antifungal activity (MIC) in vitro against organisms viz. B. subtilis, S. aureus, E. coli, P. aeruginosa, and C. albicans taking ciprofloxacin, ampicillin, streptomycin, penicillin-G, fluconazole, and nystatin as the standard drugs. Some of the compounds have shown significant activities.

Regioselective reaction: Synthesis, characterization and pharmacological activity of some new Mannich and Schiff bases containing sydnone

A novel series of 1-substituted aminomethyl-3-[1-(4-isobutylphenyl)ethyl]- 4-(3-aryl-4-sydnonylidene) amino-1,2,4-triazol-5-thiones (9), was prepared from the 3-[1-(4-isobutylphenyl)ethyl]-4-(3-aryl-4-sydnonylidene) amino 5-mercapto-1,2,4-triazoles (8) by aminomethylation with formaldehyde and secondary amine. The structures of Schiff bases (8) and Mannich bases (9) were characterized on the basis of IR, NMR, mass spectra1 data and elemental analysis. The newly synthesized compounds were screened for their anti-inflammatory and analgesic activities. Mannich bases (9) carrying piperidine and morpholine residues showed promising anti-inflammatory and analgesic activity.

Synthesis of 2 H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes

A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupl

Convenient access to 1,3,4-trisubstituted pyrazoles carrying 5-nitrothiophene moiety via 1,3-dipolar cycloaddition of sydnones with acetylenic ketones and their antimicrobial evaluation

Novel 1-aryl-3-(5-nitro-2-thienyl)-4-aroyl-pyrazoles 7 have been synthesized by the 1,3-dipolar cycloaddition of 3-arylsydnones 3 with 1-aryl-3-(5-nitro-2-thienyl)-2-propyn-1-ones 6. The newly synthesized compounds were well characterized by elemental analysis, IR, 1H NMR and mass spectral studies. They were also screened for their antibacterial and antifungal activities against a variety of microorganisms and the results of such studies have been discussed in this article.

Synthesis and evaluation of phenyl substituted sydnones as potential DPPH-radical scavengers

A series of phenyl substituted sydnones has been synthesized and their radical-scavenging activity has been studied on DPPH free radical. Out of eighteen compounds screened, nine compounds show interesting activity. A mechanism is presented whereby sydnones scavenge DPPH radical through donating H-atom at 4th-position. Its strong radical-scavenging activity mainly arises from 1, 2, 3-oxadiazolium-5-olate ring. Different substituents and their positions on the phenyl ring differently influence DPPH scavenging activity and therefore, may provide clues to design and develop better free-radical scavenging sydnones with multiple activities.

Microwave-assisted synthesis of N-arylglycines: Improvement of sydnone synthesis

Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.

INHIBITORS OF FACTOR XA WITH A NEUTRAL P1 SPECIFICITY GROUP

The present application describes inhibitors of factor Xa with a neutral P1 specificity group of formula I: STR1 or pharmaceutically acceptable salt forms thereof, wherein R and E may be groups such as methoxy and halo.