7614-53-1

Usage

Chemical class

Sydnone derivative

Biological activities

Possesses unique and diverse biological activities

Reactivity

Highly reactive and stable free radical

Applications

Spin probe in electron paramagnetic resonance (EPR) spectroscopy
Precursor for synthesis of biologically active compounds
Potential use in organic electronics and photochemistry

Unique properties

Unique electronic and structural properties

Potential for research and development

Interesting target for further research and development in organic chemistry

InChI:InChI=1/C9H6N2O4/c12-8-5-11(10-15-8)7-3-1-6(2-4-7)9(13)14/h1-5H,(H-,10,12,13,14)/p+1

Upstream product

• 111831-83-5 4-((carboxymethyl)(nitroso)amino)benzoic acid 
• 5698-54-4 N-(p-carboxyphenyl)glycine 
• 150-13-0 4-amino-benzoic acid 

Downstream Products

• 1620220-62-3 4-bromo-3-(4-carboxyphenyl)-1,2,3λ⁵-oxadiazol-3-ylium-5-olate 
• 1620220-63-4 3-(4-carboxyphenyl)-4-chloro-1,2,3λ⁵-oxadiazol-3-ylium-5-olate 
• 950664-60-5 4-(5-methyl-[1,3,4]-oxadiazolin-2-one-3-yl)benzoyl chloride 
• 666751-33-3 3-(4-carboxy)phenyl-5-methyl-[1,3,4]-oxadiazolin-2-one 

Relevant academic research and scientific papers

Sydnone Reporters for Highly Fluorogenic Copper-Free Click Ligations

Bioorthogonal fluorescent turn-on reactions are attractive for the sensitive real-time detection of a variety of phenomena including bioconjugation, chemical reactivity, and material assembly. Herein we describe the use of 3,4-disubstituted sydnones, a singular class of mesoionic dipoles, for highly fluorescent turn-on copper-free click cycloadditions with the fluorogenic dibenzocyclooctyne Fl-DIBO. Coherent with time-dependent density functional theory calculations, the pyrazole cycloadducts were found to be highly fluorescent with compelling photophysical properties including excellent fluorescence enhancement (up to 240-fold), high quantum yields (over 45%), and large Stokes shift (over 100 nm). Furthermore, the good stability and reactivity of 4-chlorosydnones with Fl-DIBO allowed us to employ them as chemical reporters for the challenging detection of modified-proteins in complex cellular extracts, with exquisite specificity in no-wash conditions. This novel fluorogenic system significantly expands our chemical biology toolbox and should be beneficial in countless applications.

SYDNONE DERIVATIVES FOR CONJUGATION OF COMPOUNDS OF INTEREST

The present invention relates to a process for the preparation of a first compound of interest C1 functionalized with a sydnone compound and to the corresponding functionalized C1 compound of interest. The present invention also relates to a process for the preparation of a conjugate of two compounds of interest C1 and C2 implying a sydnone compound and to the obtained conjugate. The present invention also relates to a process for preparing a compound of interest C2 comprising a strained alkyne moiety functionalized with a sydnone and to the corresponding functionalized compound of interest C2. It also relates to novel sydnone compounds substituted in position 4, which may be used in the above processes.

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 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.