1008-78-2

Basic information

• Product Name: 5-amino-3-phenyl-1,2,3-oxadiazol-3-ium chloride
• CAS NO: 1008-78-2
• Molecular Formula: C₈H₈N₃O*Cl
• Molecular Weight: 197.6216
• Mol File: 1008-78-2.mol

Chemical Properties

• CAS DataBase Reference: 5-amino-3-phenyl-1,2,3-oxadiazol-3-ium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-3-phenyl-1,2,3-oxadiazol-3-ium chloride(1008-78-2)
• EPA Substance Registry System: 5-amino-3-phenyl-1,2,3-oxadiazol-3-ium chloride(1008-78-2)

Safety Data

• Hazardous Substances Data: 1008-78-2(Hazardous Substances Data)

Upstream product

• 827-51-0 N-nitroso-N-phenyl-glycine nitrile 
• 3009-97-0 N-phenylglycinonitrile 
• 62-53-3 aniline 

Downstream Products

• 17572-02-0 5-nitrosoamino-3-phenyl-[1,2,3]oxadiazolium betaine 
• 31180-71-9 acetyl(3-phenyl-1,2,3-oxadiazol-3-ium-5-yl)amide 
• 10111-79-2 3-phenyl-5-ureido-[1,2,3]oxadiazolium betaine 
• 98248-06-7 5-(4-acetylamino-benzenesulfonylamino)-3-phenyl-[1,2,3]oxadiazolium betaine 
• 96716-49-3 5-(4-amino-benzenesulfonylamino)-3-phenyl-[1,2,3]oxadiazolium betaine 
• 96432-38-1 (butylcarbamoyl)(3-phenyl-1,2,3-oxadiazol-3-ium-5-yl)amide 

Relevant articles and documents

Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes

Emerging applications in the field of chemical biology are currently limited by the lack of bioorthogonal reactions allowing both removal and linkage of chemical entities on complex biomolecules. We recently discovered a novel reaction between iminosydnones and strained alkynes leading to two products resulting from ligation and fragmentation of iminosydnones under physiological conditions. We now report the synthesis of a panel of substituted iminosydnones and the structure reactivity relationship between these compounds and strained alkyne partners. This study identified the most relevant substituents, which allow to increase the rate of the transformation and to develop a bifunctional cleavable linker with improved kinetics.

Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes

We report the discovery of a new bioorthogonal click-and-release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target-fishing applications. This click-and-release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment

A series of analogues of the non-steroidal anti-inflammatory drug (NSAID) sulindac 1 were synthesised tethered to nitric oxide (NO) donating functional groups. Sulindac shows antiproliterative effects against immortal PC3 cell lines. It was previously demonstrated that the effect can be enhanced when tethered to NO releasing groups such as nitrate esters, furoxans and sydnonimines. To explore this approach further, a total of fifty-six sulindac-NO analogues were prepared and they were evaluated as NO-releasing cytotoxic agents against prostate cancer (PCa) cell lines. Compounds 1k and 1n exhibited significant cytotoxic with IC50 values of 6.1 ± 4.1 and 12.1 ± 3.2 μM, respectively, coupled with observed nitric oxide release.

Novel amino acids: Synthesis of furoxan and sydnonimine containing amino acids and peptides as potential nitric oxide releasing motifs

The incorporation of furoxan and sydnonimine ring systems into amino acid side chains is demonstrated with the preparation of four novel amino acids which carry these nitric oxide-releasing motifs. N-((4-Nitrophenoxy)carbonyl)-3- phenylsydnonimine 9 and bis(phenylsulfonyl)furoxan 10 are the key intermediates for introducing the heterocycle side chains onto appropriate amine and alcohol functionalities respectively. Furoxan 5 and 7 both displayed NO release based on determination of nitrite production. Orthogonal amino acid protecting group strategies were deployed to demonstrate that the amino acids could be incorporated into peptide frameworks. By way of demonstration the amino acids were placed centrally into several tripeptide motifs. Griess test assays showed that these amino acids released NO in the presence of γ-glutathione (GST). is

An efficient, one-pot synthesis of 3-alkyl or aryl sydnoneimines

In a 'one-pot' process, a variety of 3-alkyl and 3-aryl sydnoneimine hydrochlorides can be prepared in high yield, under mild conditions, by nitrosation of the corresponding aminoacetonitrile with isoamyl nitrite in diethyl ether followed by cyclization w