cas 33125-97-2, Etomidate | Articles data

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Synthesis of [1-11C]ethyl iodide from [11C]carbon monoxide and its application in alkylation reactions
A method is presented for preparing [1-11C]ethyl iodide from [11C]carbon monoxide. The method utilizes methyl iodide and [ 11C]carbon monoxide in a palladium-mediated carbonylation reaction to form a mixture of [1-11C]acetic acid and [1-11C]methyl acetate. The acetates are reduced to [1-11C]ethanol and subsequently converted to [1-11C]ethyl iodide. The synthesis time was 20 min and the decay-corrected radio-chemical yield of [1-11C]ethyl iodide was 55 ± 5%. The position of the label was confirmed by 13C- labelling and 13C-NMR analysis. [1-11C]Ethyl iodide was used in two model reactions, an O-alkylation and an N-alkylation. Starting with approximately 2.5 GBq of [11C]carbon monoxide, the isolated decay-corrected radiochemical yields for the ester and the amine derivatives were 45 ± 0.5% and 25 ± 2%, respectively, based on [ 11C]carbon monoxide. Starting with 10 GBq of [11C]carbon monoxide, 0.55 GBq of the labelled ester was isolated within 40 min with a specific radioactivity of 36 GBq/μmol. Copyright
Eriksson, Jonas,Antoni, Gunnar,Langstroem, Bengt
p. 723 - 731
(2004)
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A Continuous-Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of Etomidate Derivatives
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.
Baumann, Marcus,Baxendale, Ian R.
p. 6518 - 6524
(2017/12/02)

Ruthenium-containing P450 inhibitors for dual enzyme inhibition and DNA damage
Cytochrome P450s are key players in drug metabolism, and overexpression in tumors is associated with significant resistance to many medicinal agents. Consequently, inhibition of P450s could serve as a strategy to restore drug efficacy. However, the widespread expression of P450s throughout the human body and the critical roles they play in various biosynthetic pathways motivates the development of P450 inhibitors capable of controlled local administration. Ruthenium complexes containing P450 inhibitors as ligands were synthesized in order to develop pro-drugs that can be triggered to release the inhibitors in a spatially and temporally controlled fashion. Upon light activation the compounds release ligands that directly bind and inhibit P450 enzymes, while the ruthenium center is able to directly damage DNA.
Zamora, Ana,Denning, Catherine A.,Heidary, David K.,Wachter, Erin,Nease, Leona A.,Ruiz, José,Glazer, Edith C.
p. 2165 - 2173
(2017/02/26)

Synthesis of fused imidazoles, pyrroles, and indoles with a defined stereocenter α to nitrogen utilizing mitsunobu alkylation followed by palladium-catalyzed cyclization
Nitrogen-containing fused heterocycles comprise many compounds that demonstrate interesting biological activities. A new synthetic approach involving Mitsunobu alkylation of imidazoles, pyrroles, and indoles followed by palladium-catalyzed cyclization has been developed providing access to fused heterocycles with a defined stereochemistry α to nitrogen. While ethyl imidazole or indole carboxylates are good substrates for Mitsunobu alkylation with optically pure secondary benzylic alcohols, the corresponding pyrroles are poor substrates presumably due to the increased pKa of the NH. The presence of a synthetically versatile trichloroacetyl functional group on the pyrroles significantly reduces the pKa and thereby facilitates Mitsunobu alkylation. Subsequent cyclization of the alkylated products mediated by palladium in the presence or absence of a ligand gave fused heterocycles in good to excellent yields.
Laha, Joydev K.,Cuny, Gregory D.
experimental part
p. 8477 - 8482
(2011/12/04)