26731-64-6

Usage

InChI:InChI=1/C13H17N2O/c1-12(2)13(3,4)15(16)11(14-12)10-8-6-5-7-9-10/h5-9H,1-4H3

Upstream product

• 61919-29-7 2-phenyl-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazolyl-1-oxy 
• 18390-00-6 2-phenyl-4,4,5,5-tetramethylimidazolin-3-oxide-1-oxyl 
• 14384-45-3 N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine 
• 20485-44-3 2,3-dimethyl-2,3-diaminobutane 
• 351902-03-9 2-Phenyl-4,4,5,5-tetramethylimidazolidine 
• 3964-18-9 2,3-dimethyl-2,3-dinitrobutane 

Downstream Products

• 49837-79-8 4-carboxy-2,5-dihydro-2,2,5,5-trimethyl-3-imidazolin-1-oxyl 3-oxide 
• 90277-76-2 2,2,5,5-Tetramethyl-3-oxy-2,5-dihydro-1H-imidazole-4-carboxylic acid 
• 66166-73-2 4,4,5,5-tetramethyl-2-phenyl-4,5-dihydro-1H-imidazole 
• 61919-29-7 2-phenyl-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazolyl-1-oxy 
• 316147-91-8 bis(2-phenyl-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazoline-1-oxyl)bis(trifluoroacetate)copper(II) 

Relevant academic research and scientific papers

Photochemical activities of n-nitroso carboxamides and sulfoximides and their application to DNA cleavage

N-Nitroso compounds containing benzene, fluorene or fluorenone rings were synthesized. Photolysis of these compounds with 312-nm UV light provided the NO species, the presence of which was corroborated by use of an EPR method and of 2phenyl-4,4,5,5-tetramethylimidazolin-loxyl 3-oxide (PTIO) as a trapping agent. During irradiation of N-methylN-nitroso-9-fluorenone carboxamide (14c) in the absence of PTIO, it underwent decomposition followed by re-combination to give the heterocyclic nitric oxide radical 15. Incorporation of intercalating moieties endowed the Nnitroso compounds with DNA-cleaving ability through single-strand scission upon UV irradiation in a phosphate buffer (pH 5.0-8.0) under aerobic conditions.

2-Phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-Oxide (PTIO?) Radical Scavenging: A New and Simple Antioxidant Assay in Vitro

Current in vitro antioxidant assays have several limitations, which frequently cause inconsistent results. The study develops a new antioxidant assay using the 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO?). After the in

A two-photon excitable and ratiometric fluorogenic nitric oxide photoreleaser and its biological applications

We report for the first time the development of a two-photon excitable NO photoreleaser, CNNO, for ratiometric imaging and tracking of NO release in live cells. CNNO exhibits the merits of spatiotemporal control in both the site-specific NO release in the

Synthesis and Straightforward Quantification Methods of Imino Nitroxide-Based Hexaradical Architecture on a Cyclotriphosphazene Scaffold

The synthesis of a homogeneous neutral hexaradical architecture consisting of six imino nitroxide radical moieties covalently bonded on a cyclotriphosphazene scaffold was reported. The synthesis of hexaradical imino nitroxide compounds follows the Ullman procedure involving the condensation of 2,3-bis(hydroxylamino)-2,3-dimethylbutane with hexa-(4-formylphenoxy)cyclotriphosphazene (3) followed by oxidation of the condensation product hexa-[4-(1-hydroxy-4,4,5,5-tetramethyl-2-imidazoline-2-yl)phenoxy]cyclotriphosphazene (2) by NaIO4. Characterization of hexaradical was performed by X-ray and SQUID in solid state and by EPR, absorption spectroscopy, and electrochemistry in solution. CV of 1 shows an oxidation peak at 1.184 V (vs SCE) and a reduction peak at -0.883 V, both characteristics of the presence of phenyl imino nitroxide (7) moieties, suggesting that the contribution of the cyclotriphosphazene core is negligible. Attention was particularly focused on developing methods, UV-vis spectroscopy and square-wave voltammetry, to quantify the number of radicals in a way to confirm easily and rapidly the polyradicals' structure.

Photocalibrated NO Release from N-Nitrosated Napthalimides upon One-Photon or Two-Photon Irradiation

NO donors are routinely used as the exogenous source in in vitro studies. However, the kinetics or the dose of NO release from the existing donors is not readily monitored. This complicates the elucidation of the involvement of NO in a biological response. We report herein a series of NO donors (NOD545a-g), whose NO release is triggered by UV light at 365 nm or a two-photon laser at 740 nm, and importantly, their NO release is accompanied by a drastic fluorescence turn-on, which has been harnessed to follow the kinetics and dose of NO release in a real-time fashion with spectroscopic methods or microscopic methods in in vitro studies. These merits have rendered NOD545a-g useful molecular tools in NO biology.

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.

A new method for the reduction of nitronyl nitroxides

Reduction of nitronyl nitroxides using hexamethylenetetramine is a very convenient method for preparing the corresponding imino nitroxides and 2-imidazoline N-oxides.

Nitronyl and imino nitroxides: Improvement of Ullman's procedure and report on a new efficient synthetic route

The synthesis of nitronyl and imino nitroxides has been reexamined with the aim of both increasing yields and of offering opportunities for new structures. The conditions for the formation of 2,3-bis(hydroxyamino)-2,3-dimethylbutane, the key intermediate of Ullman's route, have been carefully studied, and a new procedure is proposed, which affords the free base in a very pure form and up to 60% yield. Full characterization of this intermediate including an X-ray crystal structure is presented. An alternative synthetic route through 2,3-diamino-2,3-dimethylbutane and the corresponding imidazolidines which bypasses the delicate synthesis of the bis(hydroxyamino) compound is described. It is shown that 3-chloroperbenzoic acid is an effective oxidant for the transformation of adequately substituted imidazolidines into nitronyl nitroxides, which are obtained in high yield. An illustration of the potentialities of this new route, a new nitronyl nitroxide with two ethyl substituents in positions 4 and 5 of the imidazoline ring, is reported. The scope and limitations of the two routes are discussed.

Deoxygenation reaction of phenyl nitronyl nitroxides with the strong acceptors TCNQF4 and TCNQ

The reaction of certain phenyl nitronyl nitroxide derivatives with strong acceptors such as TCNQF4 or TCNQ in appropriate solvents give the corresponding imine nitroxide derivatives by an anomalous deoxygenation reaction with acceptors in a sel

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.