ライフサイエンスコーパス: nitrone

1 r aggregation) hindering radical addition to nitrone.

2 by the antioxidant alpha-phenyl-N-tert-butyl nitrone.

3 ments of GS.-5, 5-dimethyl1pyrroline N-oxide nitrone.

4 a novel, brain-permeable spin trap, azulenyl nitrone.

5 l hydroxylamine to provide the corresponding nitrone.

6 hiated alkoxyallene to an enantiopure cyclic nitrone.

7 loaddition of a glyoxylate-based homoallylic nitrone.

8 thesized starting from an l-tartaric derived nitrone.

9 catalyst in the one-pot tandem synthesis of nitrones.

10 e-derived alpha,beta-unsaturated pyrrolidine nitrones.

11 ition reactions with both acyclic and cyclic nitrones.

12 es which are combined with aldehydes to form nitrones.

13 yn-selenoxide elimination to provide N-vinyl nitrones.

14 onic properties to those of alkoxyphosphoryl nitrones.

15 compared to those in DMPO and alkoxycarbonyl nitrones.

16 ones compared to DMPO and the alkoxycarbonyl nitrones.

17 trone is more exoergic than the carbonylated nitrones.

18 ar H-bonding is favored for alkoxyphosphoryl nitrones.

19 bearing indoline systems to their respective nitrones.

20 es and 25.8 kcal/mol for C-(methoxycarbonyl) nitrones.

21 introduction of a cyanomethyl group onto the nitrones.

22 g this model, the k(app) for the reaction of nitrone 1, 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-

23 valuation of the BBB penetration of selected nitrones 1, 2, 10, and 11 using the PAMPA-BBB assay show

24 ated (MTT assay) studies clearly showed that nitrones 1-3 and 10 give rise to significant neuroprotec

25 d for necrotic cell death (LDH release test) nitrones 1-3, 6, 7, and 9 proved to be neuroprotective a

26 f AMPO, and of the novel and analogous amido nitrone 2-amino-5-carbamoyl-5-methyl-1-pyrroline N-oxide

27 Permeable quinoline nitrones 2 and 3 show potent combined antioxidant and ne

28 ; and we synthesized a novel, cell permeable nitrone, 2-2-3,4-dihydro-2H-pyrrole 1-oxide (EMEPO).

29 In DMSO, the half-lives of nitrone 3 and 4-OOH adducts were double that of PBN, sug

30 eement with their high lipophilicity values, nitrone 3 was insoluble in water, while nitrone 4 exhibi

31 The Z and E nitrones 38 and 39 from condensation of aldehyde 20 with

32 The synthesis of the acid nitrone 4 and its corresponding tert-butyl ester 3 was i

33 ues, nitrone 3 was insoluble in water, while nitrone 4 exhibited a poor water solubility.

34 of an alpha-(4-pyridyl-1-oxide)-N-tert-butyl-nitrone (4-POBN)-ethanol spin-trapping system, the 4-POB

35 The nitrone 5-carbamoyl-5-methyl-1-pyrroline N-oxide (AMPO)

36 been able to isolate the two enantiomers of nitrone 5.

37 With enantiomerically pure nitrone 5a and 5b we explored whether one of these isome

38 emonstrate that the spin trapping of O2*- by nitrone 5a and nitrone 5b affords the identical EPR spec

39 the spin trapping of O2*- by nitrone 5a and nitrone 5b affords the identical EPR spectra and lifetim

40 ith C-(4-benzyloxyphenyl)-N-(4-fluorophenyl)-nitrone (8), intramolecular nucleophilic displacement at

41 The nitrone above is readily available via the intramolecula

42 e (H(2)O(2)) in the presence of DMPO, a DMPO nitrone adduct could be detected by immuno-spin trapping

43 The formation of this nitrone adduct depended on the concentrations of GSH, LP

44 te ions of both the native and the mono-DMPO nitrone adduct of human myoglobin.

45 MPO, we detected an LPO radical-derived DMPO nitrone adduct using enzyme-linked immunosorbent assay a

46 The level of this nitrone adduct was decreased significantly by azide, cat

47 The nitrone adduct was repaired on a time scale consistent w

48 , but is subsequently oxidized to the stable nitrone adduct, which can be detected and visualized by

49 roline-N-oxide (DMPO), thus forming DMPO-DNA nitrone adducts (referred to here as nitrone adducts); (

50 Because both protein and DNA nitrone adducts are formed, it is important that the DNA

51 on of nitrone adducts; and (iii) analysis of nitrone adducts by heterogeneous immunoassays using Abs

52 ally recognizes protein radical-derived DMPO nitrone adducts has been developed.

53 serum to detect protein radical-derived DMPO nitrone adducts in the hemoprotein Mycobacterium tubercu

54 k demonstrates that the formation of protein nitrone adducts is dependent on the concentrations of te

55 iments for the purpose of detecting DMPO-DNA nitrone adducts should be conducted over a range of time

56 l-1-pyrroline N-oxide (DMPO), forming stable nitrone adducts that are then detected using an anti-DMP

57 Furthermore, the formation of protein-DMPO nitrone adducts was accelerated in the presence of isoni

58 Protein-DMPO nitrone adducts were also generated by a continuous flux

59 The DMPO nitrone adducts were analyzed by mass spectrometry (MS)

60 (DMPO) was included in the reaction mixture, nitrone adducts were detected by immuno-spin trapping.

61 MPO-DNA nitrone adducts (referred to here as nitrone adducts); (ii) purification of nitrone adducts;

62 s in situ and in real time, forming DMPO-DNA nitrone adducts, but preventing both 8-oxo-7,8-dihydro-2

63 radicals, thus ensuring a high yield of DNA nitrone adducts.

64 nst protein 5,5-dimethyl-1-pyrroline N-oxide-nitrone adducts.

65 -pyrroline glytathionyl N-oxide glytathionyl nitrone adducts.

66 re as nitrone adducts); (ii) purification of nitrone adducts; and (iii) analysis of nitrone adducts b

67 DFT) calculations to assess the viability of nitrone-alkene (3 + 2) cycloaddition reactions proposed

68 Reaction of 2,4-dienals with nitrones allows for a highly regio- and stereoselective

69 In mice, the cyclic nitrones ameliorated the damaging effects of oxidative s

70 sannular 1,3-dipolar cycloaddition between a nitrone and an enone in a nine-membered macrocycle.

71 Spin trapping using a nitrone and electron paramagnetic resonance (EPR) spectr

72 ionalize the long-range coupling between the nitrone and the beta-CD, as well as the stability of the

73 hich the lithium atom is coordinated to both nitrone and ynolate, the reaction takes place in one sin

74 -limiting step of 29.9 kcal/mol for C-methyl nitrones and 25.8 kcal/mol for C-(methoxycarbonyl) nitro

75 (II) carboxylate catalyzed reactions between nitrones and a beta-TBSO-substituted vinyldiazoacetate.

76 Cascade reactions involving nitrones and allenes are known to facilitate the rapid s

77 dihydropyrido[1,2-a]indoles from mixtures of nitrones and allenoates has been developed.

78 synthesized by the [3 + 2] cycloaddition of nitrones and arynes.

79 r cycloadditions between d-arabinose-derived nitrones and d-mannitol-derived trans-olefins have been

80 de reaction of N-aryl-alpha,beta-unsaturated nitrones and electron-deficient allenes has been discove

81 The mechanism of the reaction between nitrones and lithium ynolates has been studied using DFT

82 e constants were similar among the different nitrones and not that significantly different from that

83 emonstrated with a variety of formamides and nitrones and provided a direct route to alpha-(N-hydroxy

84 Energies of optimized geometries of nitrones and their corresponding *OH adducts were calcul

85 ained by a 1,3-dipolar cycloaddition between nitrones and vinylsulfones.

86 ocatechin gallate, alpha-phenyl-N-tert-butyl nitrone, and ebselen significantly suppressed iNOS trans

87 l) cyclobutylamine to the N-hydroxyamine and nitrone, and rat P450 2B1-catalyzed and rabbit P450 2B4-

88 andem condensation to oximes, cyclization to nitrones, and 1,3-dipolar cycloaddition to tricyclic iso

89 e as a dipolarophile with azomethine ylides, nitrones, and nitrile oxides in good yields.

90 thods with facilitated access to challenging nitrones, and shown that these transformations can be co

91 itroxyl O bonds is smaller in phosphorylated nitrones, and that aspect appears to account for the lon

92 The reaction works best with alpha,N-diaryl nitrones, and the conditions are compatible with a range

93 interest in the pharmacological activity of nitrones, and there is, therefore, a pressing need to de

94 Nitrones are important building blocks for natural and b

95 This indicated the cyclic nitrones are inherently more effective radical traps tha

96 Nitrones are key intermediates in organic synthesis and

97 Azulenyl nitrones are novel chain-breaking antioxidants with low

98 C(sp(2))-H bond functionalization in cyclic nitrones are reported.

99 Therefore, nitrones are still of great interest and in the limeligh

100 The phenylselenenyl-containing nitrones are then oxidized to selenoxides which undergo

101 BB) of (Z)-alpha-aryl and heteroaryl-N-alkyl nitrones as potential agents for stroke treatment.

102 the nucleophilic nature of O2*- addition to nitrones as well as the role of intramolecular hydrogen

103 work, a series of alpha-phenyl-N-tert-butyl nitrones bearing one, two, or three substituents on the

104 ent oxidase that generates roquefortine L, a nitrone-bearing intermediate in the biosynthesis of oxal

105 amide or an ester as attached groups on the nitrone can be ideal in molecular tethering for improved

106 uch as spin traps (alpha-phenyl-N-tert-butyl nitrone), catalytic antioxidants (superoxide dismutase [

107 addition, is more positive in phosphorylated nitrones compared to DMPO and the alkoxycarbonyl nitrone

108 The majority of nitrones compete with DMSO for hydroxyl radicals, and mo

109 1,3-dipolar cycloaddition reaction between a nitrone component, equipped with a 9-ethynylanthracene o

110 a dimethylphenol fused to a 7-membered ring nitrone (compound 6h), inhibited lipid peroxidation in v

111 At high nitrone concentrations, a second paramagnetic species, v

112 The beta-cyclodextrin (beta-CD)-cyclic nitrone conjugate, 5-N-beta-cyclodextrin-carboxamide-5-m

113 animine N-oxide (EBN), which is the simplest nitrone containing an alpha-H and a tertiary alpha'-C at

114 ch heterocycle, or a dimethylphenol, (2) the nitrone-containing ring comprised five, six, or seven at

115 Either of these two nitrones could, in principle, be utilized for the prepar

116 irectional approach involving intramolecular nitrone cycloaddition as the key step.

117 Application of intramolecular 1,3-dipolar nitrone cycloaddition reaction on carbohydrate-derived p

118 A stereoselective intramolecular 1,3-dipolar nitrone cycloaddition useful in the synthesis of chroman

119 a bis(cyanoalkenyl)oxime and proceeding via nitrone cycloadditions have been unraveled through a ser

120 Moreover, the strategic manipulation of nitrone cycloadducts demonstrates the utility of this me

121 and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.

122 we also tested our findings on chalcone and nitrone data from the current literature.

123 ts into the reactivity of free radicals with nitrone derivatives have been proposed.

124 A novel series of alpha-phenyl-N-tert-butyl nitrone derivatives, bearing a hydrophobic chain on the

125 tion between copper(I) acetylides and cyclic nitrones derived from chiral amino alcohols and glyoxyli

126 ng with alpha-(4-pyrridyl-1-oxide)-N-t-butyl-nitrone-ethanol confirmed the generation of HO., and inj

127 ng an alpha-(4-pyridyl-1-oxide)-N-tert-butyl-nitrone/ethanol spin-trapping system, we were able to de

128 The alkyne molecule approaches the nitrone exclusively anti to the large substituent next t

129 elective nucleophilic addition to the cyclic nitrone followed by a combination of two simultaneous an

130 carboxylation to give an azomethine ylide or nitrone followed by intramolecular dipolar cycloaddition

131 ifluoromethylation of beta,gamma-unsaturated nitrones followed by reduction of the double bond can ci

132 tion of enolizable cyclic 1,3-dicarbonyls to nitrones, followed by a spontaneous intramolecular reorg

133 udy demonstrates the suitability of the AMPO nitrone for use as a spin trap to study radical producti

134 rones were predicted to be the most suitable nitrones for spin trapping of *OH due to the similarity

135 Analogs of the cyclic nitrone free radical trap 1 (3,3-dimethyl-3,4-dihydroiso

136 N-oxide) of the previously described cyclic nitrone free radical trap 1 (3,3-dimethyl-3,4-dihydroiso

137 An electrocyclization route to azetidine nitrones from N-alkenylnitrones was discovered that prov

138 Nitrone functionality in roquefortine L was confirmed by

139 In most cases, the nitrones gave rise to a standard six-line EPR spectrum w

140 undergoes a stepwise cycloaddition with the nitrone, generating a five-membered ring intermediate.

141 e reactions results from both control of the nitrone geometry and selective partitioning of the react

142 Recently, a family of ester-containing nitrones has been prepared, which appears to have distin

143 Nitrones have also found applications as therapeutic age

144 dition reactions of enoldiazoacetamides with nitrones have been developed.

145 s for superoxide radical trapping by various nitrones have been found to predict favorable formation

146 ucturally and electronically diverse N-vinyl nitrones have been synthesized by a two-step method.

147 4-elimination to provide the desired N-vinyl nitrone in good to excellent yields.

148 Subsequent treatment of the nitrone in refluxing toluene with substituted actetylene

149 ndicated that photochemical rearrangement of nitrones in benzene afforded reasonably good yields (30-

150 c tertiary N-oxides (and with one protonated nitrone) in different mass spectrometers.

151 Ester-containing nitrones, including 5-tert-butoxycarbonyl-5-methyl-1-pyr

152 yl, thienyl, and pyridyl halides with cyclic nitrones, including DMPO.

153 FeTBAP, ebselen, and alpha-phenyl-tert-butyl nitrone) inhibited DOX-induced eNOS transcription.

154 eactions and organometallic additions to key nitrone intermediates, formed in turn by oxidation proce

155 All this makes nitrones intriguing and valuable compounds for fundament

156 Addition of *OH to a phosphoryl-substituted nitrone is more exoergic than the carbonylated nitrones.

157 Substrates in which the nitrone is part of a fused bicyclic ring system have tra

158 the first [4+2] cycloaddition of an N-vinyl nitrone is reported.

159 tituted 1,1,1-trifluoromethylstyrene-derived nitrones is described.

160 bstituted formamides and LDA to N-tert-butyl nitrones is described.

161 is of a new type of heterodiene, the N-vinyl nitrone, is described.

162 Synthesized nitrone matched the unknown metabolite with identical re

163 Applied to the chiral nitrone MiPNO, this transformation provides a straightfo

164 fin functionality at C-1 or C-3 or C-5 and a nitrone moiety at C-2 or C-3 as appropriate has resulted

165 intermolecular nucleophilic addition of two nitrone molecules, was also observed but to a lesser ext

166 In this network, nitrone N bearing a 6-methylamidopyridine recognition si

167 erizes to a 3,4-dihydro-1,2,4-triazine-based nitrone, namely 6-phenyl-3-pyridin-2-yl-2,3-dihydro-1,2,

168 nd more persistent O2(*-) adduct compared to nitrones not conjugated to beta-CD.

169 h this topology using two maleimides and two nitrones of different sizes-either short or long and eac

170 Starting from a chiral furanone, the nitrone-olefin [3 + 2] cycloaddition can be used to obta

171 t involves a stereocontrolled intramolecular nitrone-olefin dipolar cycloaddition has been developed

172 addition reactions of a carbohydrate-derived nitrone on diversely functionalized calix[4]arenes.

173 rotonated aromatic tertiary N-oxides and one nitrone, only three protonated amines were found to form

174 ort-lived free radicals, consists of using a nitrone or nitroso compound to "trap" an unstable free r

175 on the high rates of addition of radicals to nitrones or nitroso compounds (spin traps; STs).

176 of the reaction is a rare case in which the nitrone oxygen acts as a nucleophile by attacking the ce

177 lies on the use of a chiral auxiliary on the nitrone partner.

178 potency of STAZN over the three alpha-phenyl nitrones PBN, S-PBN, and NXY-059.

179 he radical scavenger alpha-phenyl-tert-butyl nitrone (PBN) (100 mg/kg q8h i.p.) beginning at the time

180 The antioxidant phenyl-alpha-tert-butyl nitrone (PBN) arrested the oxidative damage-mediated los

181 f the FR scavenger alpha-phenyl-N-tert-butyl-nitrone (PBN) attenuates hypoxic-ischemic white matter d

182 alpha-Phenyl-tert-butyl nitrone (PBN) is a nitrone spin trap, which has shown ef

183 nce spectroscopy and alpha-phenyl-tert-butyl nitrone (PBN) spin trapping.

184 s homogenized with alpha-phenyl-N-tert-butyl-nitrone (PBN) through electron spin resonance spectrosco

185 t of an antioxidant, alpha-phenyl-tert-butyl-nitrone (PBN) was used as a treatment strategy against o

186 Alpha-phenyl-N-t-butyl nitrone (PBN), a spin trap, scavenges hydroxyl radicals,

187 e ability of Trolox, alpha-phenyl-tert-butyl nitrone (PBN), or catalase to attenuate the methylmercur

188 spin trap inhibitor, alpha phenyl-tert-butyl nitrone (PBN).

189 ing antioxidant vs conventional alpha-phenyl nitrones previously investigated as antioxidant therapeu

190 Thus, the mechanism of E/Z isomerization of nitrones proceeds via a diradical bimolecular process in

191 ert-leucinol derived chiral auxiliary on the nitrone provided products in good diastereoselectivity.

192 yl carbon as well as on the free energies of nitrone reactivity with O2(*-) and HO2(*) were computati

193 ng bicyclic oxazine and five-membered cyclic nitrone, respectively.

194 atalyzed reaction of vinyldiazoacetates with nitrones results in a formal [3+2]-cycloaddition to gene

195 to investigate the dependence of products on nitrone ring size and tether length.

196 The nitrone slowly decomposed in acidic aqueous solution at

197 real-time trapping of DNA radicals with the nitrone spin trap 5,5-dimethyl-1-pyrroline-N-oxide (DMPO

198 We have found that the nitrone spin trap DMPO (5,5-dimethyl-1-pyrroline N-oxide

199 These techniques show that the nitrone spin trap DMPO covalently binds to one or more a

200 In this work, the synthesis of a nitrone spin trap, 4, that is tethered via amide bonds t

201 alpha-Phenyl-tert-butyl nitrone (PBN) is a nitrone spin trap, which has shown efficacy in animal mo

202 We conclude that nitrone spin traps and ebselen inhibit the DOX-induced a

203 Nitrone spin traps are commonly employed as probes for t

204 tations exist among the commonly used cyclic nitrone spin traps for biological free radical detection

205 Nitrone spin traps have been shown to scavenge O(2) (.-)

206 lysis because O(2)(*)(-) adducts with common nitrone spin traps have shorter half-lives than typical

207 Nitrone spin traps significantly inhibited the formation

208 Charge and spin densities on the nitrone spin traps were correlated with their rates of a

209 Pretreatment of cells with 100 microm nitrone spin traps, N-tert-butyl-alpha-phenylnitrone (PB

210 unprecedented among archetypal alpha-phenyl nitrone spin traps.

211 (SOD), glutathione peroxidase mimetics, and nitrone spin traps.

212 Stilbazulenyl nitrone (STAZN) is a potent antioxidant that, in a rat m

213 Stilbazulenyl nitrone (STAZN), 8, a nitronyl-substituted hydrocarbon,

214 -generation azulenyl nitrone, stilbazunenlyl nitrone (STAZN), in focal ischemic stroke.

215 We tested the second-generation azulenyl nitrone, stilbazunenlyl nitrone (STAZN), in focal ischem

216 d its deuterium-labeled analogue suggested a nitrone structure for the unknown metabolite.

217 N was orders-of-magnitude greater than other nitrones such as NXY-059.

218 Rarely observed in this class are indolic nitrones, such as avrainvillamide and waikialoid, which

219 work describes the first implementation of a nitrone synthase as a biocatalyst and establishes a nove

220 All cyclic nitrones tested were much more potent as inhibitors of l

221 this approach is a six-membered cyclic sugar nitrone that is generated in situ and trapped by an alke

222 e oxime onto the diene to afford a transient nitrone that then undergoes an intramolecular dipolar cy

223 stituted 4-chlorobutanals gives intermediate nitrones that undergo tandem cyclization and then intram

224 acetylide dianion addition to a serine-based nitrone, thereby facilitating the preparation of STX in

225 Acidic deprotection of the nitrone/TMSCF(3) adducts generates alpha-(trifluoromethy

226 Nitrone/TMSCF(3) adducts with strong electron-withdrawin

227 e formed resulting from rearrangement of the nitrone to an oxaziridine.

228 ethyl)trimethylsilane (TMSCF(3)) reacts with nitrones to afford alpha-(trifluoromethyl)hydroxylamines

229 pping of (.)OH and O2(-.) suggest the cyclic nitrones to be ideal reagents for the study of oxidative

230 efficient catalyst for the cycloaddition of nitrones to donor-acceptor cyclopropanes.

231 fied by dipolar cycloaddition reactions with nitrones to give highly substituted 4-nitro-4-isoxazolin

232 situ under mild conditions and trapped with nitrones to give isoxazolidine products in synthetically

233 The rearrangement of nitrones to lactams can be carried out by photochemical

234 dichloromethane with subsequent transfer to nitrones under smooth conditions.

235 presence of the Lewis acid Al(O(t)Bu)(3) the nitrones undergo an intramolecular [3 + 2] cycloaddition

236 s the first examples of one-pot synthesis of nitrones using recyclable multifunctional heterogeneous

237 tant thus far observed at neutral pH for any nitrones using the kinetic method employed.

238 oaddition of an intermediate homoallylic (E)-nitrone via a pathway that is stereochemically unscathed

239 viability and the oxidation potential of the nitrones was observed.

240 These nitrones were also found to efficiently trap carbon-cent

241 f superoxide radical (O2(*-)) reactions with nitrones were determined using a UV-vis stopped-flow met

242 stants for the reactivity of O2*- with model nitrones were found to correlate with the experimentally

243 ay crystal structures of substituted N-vinyl nitrones were obtained.

244 Amido and spiroester nitrones were predicted to be the most suitable nitrones

245 ries of mono-, bi-, and tricyclic ring-fused nitrones were prepared to investigate the dependence of

246 The cyclic nitrones were shown to trap (.)OH with MDL 101,002 being

247 Two bifunctional alpha-phenyl-N-cyclohexyl nitrones were synthesized with the expectation that the

248 of carinatine A, a rare naturally occurring nitrone, were formed in a single operation.

249 m of PBN, N-tert-butyl-alpha-(2-sulfophenyl) nitrone, which has similar free radical trapping activit

250 dduct formation is favored in alkoxycarbonyl nitrones, while cis adducts with intramolecular H-bondin

251 entry to densely functionalized homoallylic nitrones whose intramolecular annulation can be controll

252 excess MeMgCl resulted in the formation of a nitrone, whose structure was confirmed by X-ray crystall

253 Reaction of azulenyl nitrone with a free radical forms a nitroxide adduct tha

254 The reaction of the nitrone with diethyl acetylenedicarboxylate readily gene

255 A spirolactonyl-nitrone with rigid H-bond acceptor, 7-oxa-1-azaspiro[4.4

256 arbon, is a novel second-generation azulenyl nitrone with significantly enhanced potency as a chain-b

257 Nitrones with alkyl groups bound directly to the 1,3-dip

258 1,3-Dipolar cycloaddition reactions of nitrones with alpha,beta-unsaturated aldehydes catalyzed

259 n and efficient 1,3-dipolar cycloaddition of nitrones with different styrenes and cinnamates using a

260 re is, therefore, a pressing need to develop nitrones with improved spin trapping properties and cont

261 The mechanism of cycloaddition reactions of nitrones with isocyanates has been studied using density

262 The heterogeneous synthesis of nitrones with multifunctional catalysts is extremely att

263 minoxyls, derived from the reaction of these nitrones with O2*-.

264 Structures of nitrones with trifluoromethyl-, trifluoromethylcarbonyl-

265 to unknown mechanism of E/Z isomerization of nitrones, with important implications in 1,3-dipolar cyc

266 reaction between a novel type of ylide, i.e. nitrone ylides, and alkenes has been carried out.