117566-84-4

Basic information

• Product Name: 2-(3'-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl
• Synonyms: 2-(3'-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl
• CAS NO: 117566-84-4
• Molecular Weight: 278.288
• Mol File: 117566-84-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(3'-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3'-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl(117566-84-4)
• EPA Substance Registry System: 2-(3'-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-3-oxide-1-oxyl(117566-84-4)

Safety Data

• Hazardous Substances Data: 117566-84-4(Hazardous Substances Data)

Upstream product

• 66166-73-2 4,4,5,5-tetramethyl-2-phenyl-4,5-dihydro-1H-imidazole 
• 14384-45-3 N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine 
• 3964-18-9 2,3-dimethyl-2,3-dinitrobutane 
• 898562-18-0 1,3-dihydroxyl-2-(3'-nitrophen-1'-yl)-4,4,5,5-tetramethylimidazolidine 
• 18390-00-6 2-phenyl-4,4,5,5-tetramethylimidazolin-3-oxide-1-oxyl 
• 99-61-6 3-nitro-benzaldehyde 
• 14538-51-3 2,3-bis(hydroxyamino)-2,3-dimethylbutane monosulfate 

Relevant articles and documents

Novel 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazolines: Synthesis, selectively analgesic action, and QSAR analysis

Based on the knowledge that imidazoline can result in analgesic action due to its selective binding with the prostacyclin receptor, 20 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazolines (3a-t) were prepared in moderate yields. At 0.13 mmol/kg dose, their in vivo analgesic activities were evaluated after the mice were administered at 30, 60, 90, and 150 min. Compared with the pain threshold (12.27 ± 9.56-17.71 ± 7.00%) of normal saline (NS) receiving mice, the pain threshold (23.42 ± 8.14% to 102.58 ± 10.66%) of 3a-t receiving mice increases significantly. Considering a prostacyclin receptor targeting analgesic agent usually had bleeding action and to appraise the bleeding risk, the in vivo tail bleeding time of 1.30 mmol/kg 3a-t receiving mice was found to be ranged from 116.3 ± 8.2 s to 120.3 ± 9.2 s, which was substantially equal to that (117.8 ± 8.4 s to 119.0 ± 8.6 s) of NS receiving mice. Based on the possibility of imidazoline acting as vasodilator, the in vitro vasorelaxations of 3a-t were tested using the rat aortic strip model. When the aortic strip contracted by noradrenaline (NE, final concentration 10-7 mol/l) was treated with 3a-t (final concentration 5 × 10-4 mol/l), only lower percentage inhibitions (6.55 ± 5.70-37.40 ± 4.07%) were recorded, implying that the vasorelaxation of 3a-t was neglectable. By selecting appropriate molecular descriptors generated from e-dragon server, the QSAR model of the analgesic activities of 3a-t was constructed using the multiple linear regression method. The established QSAR model showed reasonable accuracy and thus it is promising to be used for screening new 1-oxyl-2-substitutedphenyl-4,4,5,5-tetramethylimidazoline derivatives as analgesic agents.

Synthesis and reactions of new nitronyl nitroxides

Various new 2-substituted 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-yloxyl 3-oxide mono- 1b, 7, 13a,b, 14, 15, 16, 17, 22 and biradicals 8, 9 were prepared. The nitronyl nitroxide functions were selectively reduced by Fe/HOAc to 1-hydroxyimidazoline derivatives 3b, 11, 21. The reductions by Zn/HCl led to imidazolines 4, 12. The nitronyl nitroxide functions remained inert when the 2-phenyl compound was nitrated by H2SO4/HNO3 to give nitrophenyl nitronyl nitroxide derivatives 13a,b, 14.