73941-33-0Relevant articles and documents
IMIDAZOLIUM REAGENT FOR MASS SPECTROMETRY
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Page/Page column 56-58, (2021/11/26)
The present invention relates to compounds which are suitable to be used in mass spectrometry as well as methods of mass spectrometric determination of analyte molecules using said compounds.
A Continuous-Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of Etomidate Derivatives
Baumann, Marcus,Baxendale, Ian R.
, p. 6518 - 6524 (2017/12/02)
A simple yet robust flow set-up for the efficient desulfurization of a series of thioimidazoles is presented, which generates the corresponding imidazole derivatives in high yields. The strategic choice of peristaltic over piston pumps allowed reliable delivery of the heterogeneous stream of the thioimidazole substrate into a T-piece where it reacted with NaNO2 in the presence of acetic acid. This approach enabled the controlled and safe formation of the reactive nitrosonium species without uncontrolled exposure to hazardous nitrous oxide by-products as observed in related batch protocols. The value of the resulting imidazole products was further demonstrated by their conversion into various esters representing new derivatives of the known analgesic etomidate through an efficient one-pot Corey–Gilman–Ganem oxidation procedure.
New selective inhibitors of steroid 11β-hydroxylation in the adrenal cortex. Synthesis and structure-activity relationship of potent etomidate analogues
Zolle, Ilse M.,Berger, Michael L.,Hammerschmidt, Friedrich,Hahner, Stefanie,Schirbel, Andreas,Peric-Simov, Biljana
, p. 2244 - 2253 (2008/12/22)
Derivatives of etomidate were evaluated as inhibitors of adrenal steroid 11β-hydroxylations. Stereoselective coupling by Mitsunobu produced chirally pure analogues to study the effect of configuration, modification of the ester, and substitution in the phenyl ring, with the aim to probe specific sites for introducing a radionuclide. Iodophenyl metomidate (IMTO) labeled with iodine-131 served as radioligand for structure-affinity relationship studies. We have characterized the kinetic parameters of specific 131I-IMTO binding on rat adrenal membranes and used the displacement of 131I-IMTO binding to evaluate functionalized MTO analogues. Our results indicated that (1) (R)-configuration is essential for high affinity, (2) highest potency resides in the ethyl, 2-propyl, and 2-fluoroethyl esters, and (3) substitution of the phenyl ring is well tolerated. The clinically used inhibitors metyrapone and ketoconazole inhibited 131I-IMTO binding with low affinity. Incubation of selected analogues with human adrenocortical NCI-h295 cells demonstrated a high correlation with the inhibitory effect on cortisol secretion.
Improved specific synthesis of [1′-15N]- and [3′-15N]L-histidine
Soede-Huijbregts,Van Laren,Hulsbergen,Raap,Lugtenburg
, p. 831 - 841 (2007/10/03)
Specifically, 15N-enriched L-histidines have been prepared. The labelling methodology involves introduction of labels in its precursor 1-benzyl-5-hydroxy methyl imidazole, which is converted into L-histidine via the Schoellkopf method. The procedure allows the preparation of the intermediates and finally histidine with high 15N enrichment (99%) at each position, in 29% overall yield starting with 15NH4Cl and 56% with KSC15N, respectively. Copyright
Imidazole derivatives with potential biological activity
Belgodere,Bossio,Parrini,Pepino
, p. 1051 - 1056 (2007/10/02)
A series of 1-substituted imidazole-5-carbohydroxamic acids Ia, Ib and Ie were prepared from the corresponding 5-methoxycarbonyl imidazoles (IX) obtained by a univocal synthesis starting with the reaction of the amines (III) with ethylchloroacetate. On treatment of 4(5)-methoxycarbonyl imidazoles (XI) with alkylar halides (X), on the contrary, mixtures of 1-substituted-4(or 5)-methoxycarbonyl imidazoles were obtained that, when separated by thin-layer chromatography, gave the carbohydroxamic acids Ia, Ib, Id and Ie and IIa→f. The structures of the imidazole derivatives were obtained by means of IR, NMR and UV spectra. On carrying out tests of biological activity on these compounds, it had been found that the 5-carbohydroxamic acids possess, compared to the 4-carbohydroxamic ones, a greater activity. Particularly Ib and Ib-HCl seem fairly active against Klebsiella pneumoniae and Clostridium bifermentans, Ib-HCl against Bacillus subtilis, too.
