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
• Article Data: 5

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 
• 95196-16-0 5-acetoacetylamino-3-phenyl-[1,2,3]oxadiazolium betaine 
• 89170-01-4 5-butyrylamino-3-phenyl-[1,2,3]oxadiazolium betaine 
• 10111-79-2 3-phenyl-5-ureido-[1,2,3]oxadiazolium betaine 
• 97380-09-1 5-hexanoylamino-3-phenyl-[1,2,3]oxadiazolium betaine 
• 96984-27-9 3-phenyl-5-propionylamino-[1,2,3]oxadiazolium betaine 
• 2748-37-0 N-phenyl-N'-(N-phenyl-glycyl)-urea 
• 88858-55-3 N-Butyl-N'--harnstoff 
• 96199-56-3 4-bromo-5-(3-butyl-ureido)-3-phenyl-[1,2,3]oxadiazolium betaine 
• 99870-20-9 N-Butyl-N'-(N-benzylidenamino-phenylamino-glycyl)-harnstoff 
• 93308-26-0 N-Butyl-N'--harnstoff 
• 1446512-91-9 (S)-N-((2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropoxy)carbonyl)-3-phenylsydnonimine 
• 1446513-22-9 (S)-N-((2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropoxy)carbamoyl)-3-phenylsydnonimine 
• 1446512-92-0 (S)-N-((4-(2-amino-3-methoxy-3-oxopropyl)phenoxy)carbonyl)-3-phenylsydnonimine hydrochloride 

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.

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.

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