22094-69-5

Upstream product

• 104-94-9 4-methoxy-aniline 
• 79-11-8 chloroacetic acid 
• 79-08-3 bromoacetic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 67-56-1 methanol 
• 1194-02-1 4-fluorobenzonitrile 
• 56-40-6 glycine 
• 298-12-4 Glyoxilic acid 
• 147749-35-7 2-(4-methoxyphenylamino)acetic acid methyl ester 
• 50845-77-7 N-(4-methoxy)phenylglycine ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 2749-56-6 N-(4-methoxy-phenyl)-glycine p-anisidide 
• 21535-05-7 1,4-bis-(4-methoxyphenyl)piperazine-2,5-dione 
• 22097-74-1 Cu(N-(p-methoxyphenyl)glycinate)2 
• 91246-71-8 4-((4-methoxyphenyl)amino)-butan-2-one 
• 52827-01-7 2-((4-methoxyphenyl)(nitroso)amino)acetic acid 
• 41526-30-1 1-(4-methoxyphenyl)hydantoin 
• 119750-03-7 N-chlorocarbonyl-N-(4-methoxy-phenyl)-glycine 

Relevant academic research and scientific papers

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.

Photo-polymerization properties of type-II photoinitiator systems based on 2-chlorohexaaryl biimidazole (o-Cl-HABI) and various N-phenylglycine (NPG) derivatives

A series of p-substituted NPG derivatives (Cl-NPG, OMe-NPG and NO2-NPG) comprising different push-pull characteristics have been synthesized and characterized. The NPG derivatives have good thermal stability and red shifted absorption when comp

Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ

Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.

Perovskite as Recyclable Photocatalyst for Annulation Reaction of N-Sulfonyl Ketimines

A sustainable and cost-effective manner for the photocatalytic annulation reaction of N-sulfonyl ketimines with N-arylglycines to synthesize imidazolidine-fused sulfamidates (31 examples) by employing CsPbBr3 as a heterogeneous photocatalyst has been developed. The catalyst CsPbBr3 can be simply recovered from the reaction mixture and reused at least five times without an obvious reduction in its photocatalytic reactivity, exhibiting a high catalyst economic feature.

Design, synthesis and biological evaluation of oxime lacking Psammaplin inspired chemical libraries as anti-cancer agents

In this study, we attempted the chemical simplification of Psammaplin (PsA), while retaining its activity in vitro. Inspired by the previous Structure Activity Relationship (SAR) studies on various PsA analogues and relying on the fact that oxime is metabolically unstable, we initially designed and synthesized a diverse library of PsA analogues and evaluated for cytotoxic activity. Among 32 compounds of Psammaplin analogues synthesized, the compound 10b was almost equally active as parent Psammaplin in vitro.

Exploiting Synergistic Catalysis for an Ambient Temperature Photocycloaddition to Pyrazoles

Sydnone-based cycloaddition reactions are a versatile platform for pyrazole synthesis, however they operate under harsh conditions (high temperature and long reaction times). Herein we report a strategy that addresses this limitation utilizing the synergistic combination of organocatalysis and visible-light photocatalysis. This new approach proceeds under ambient conditions and with excellent levels of regiocontrol. Mechanistic studies suggest that photoactivation of sydnones, rather than enamines, is key to the successful implementation of this process.

Mechanosynthesis of sydnone-containing coordination complexes

N-Phenyl-4-(2-pyridinyl) sydnone was shown to act as a four-electron donor N,O-ligand in unprecedented coordination complexes featuring three different metallic centers (Co, Cu, and Zn). Starting with various anilines, the use of a ball-mill efficiently enabled the synthesis of N-arylglycines, subsequent nitrosylation and cyclization into sydnones, and further metalation.

Synthesis and evaluation of photo-activatable β-diarylsydnone-L-alanines for fluorogenic photo-click cyclization of peptides

Herein, we design and synthesize a series of photoactivatable β-diarylsydnone-l-alanines (DASAs), which have excellent photo-reactivity with high fluorescence turn-on toward alkenes in a biocompatible environment. The environmental sensing properties of t

Discovery of Fluorogenic Diarylsydnone-Alkene Photoligation: Conversion of ortho-Dual-Twisted Diarylsydnones into Planar Pyrazolines

A small library of diarylsydnones (DASyds) was constructed based on aryl-pairing combinations and subjected to click reaction toward alkenes under photoirradiation with high efficiency. We were able to demonstrate the utility of DASyds for highly fluorescent turn-on ligation targeting the trans-cyclooct-4-en-1-ol moieties on protein.

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.