Synthesis of ⁷⁵Se‐2‐phenyl‐1,2‐benzisoselenazol‐3(2H)‐one (PZ 51; ebselen. A novel biologically active organo‐selenium compound

Abstract

The preparation of 75Se‐ebselen (75Se‐PZ 51) in a high radiochemical yield (∼40 %) and with a specific activity of 240 mCi/mM (8.9 GBq/mM) is described. It entails a very simple, fast and one‐pot procedure starting from elemental 75Se‐selenium. 75Se‐diselenosalicylic acid 4 is initially prepared as the key intermediate which is transformed into a corresponding dichloride 5‐before reacting with aniline to yield the desired 75Se‐ebselen. Identity and purity of the labelled compound were controlled by comparison in TLC, HPLC and MS with an authentic sample (1‐2).

Synthesis, Characterization, and Antioxidant Activity of Some Ebselen Analogues

“…The selenenyl sulfide derived from ebselen (23) and the other selenenyl sulfides (24-27) showed strong Se···O interactions. To confirm the interactions in solution, we synthesized 28-31 from the corresponding cyclic compounds (17)(18)(19)(20) by treatment with 4-MeC 6 H 4 SH. The 77 Se NMR of 28-31 showed a large downfield shift compared with PhSeSPh, thus supporting the results of the DFT calculations.…”

“…Selenenyl chloride 15, synthesized from anthranilic acid and disodium diselenide (Na 2 Se 2 ), [17] was used as a key intermediate for the synthesis of most of the compounds in the present study. The other key compound 16 was synthesized by treating 15 with an aqueous solution of ammonia.…”

Synthesis and Characterization of a New Five and Six Membered Selenoheterocyclic Compounds Homologues of Ebselen

“…The obtained residue was purified by column chromatography over silica gel (toluene-acetone 95 : 5) to provide compounds 14 and 16. (16). This compound was obtained as green oil; yield 52%, IR (NaCl) ν max absence of (C=O), 1 (20).…”

“…On the other hand, Ebselen contains a selenic moiety stabilized by intramolecular cyclisation in a cyclic N-aroyl selenamide and does not release selenium, as demonstrated by a 75 Se-labeling study, which result in its relatively nontoxic properties [16,17]. The discovery of its anti-inflammatory and glutathione-peroxidase (GPx)-like activity has initiated numerous biochemical and pharmacological investigations as well as clinical trials as an antioxidant [18][19][20][21].…”

Mehanizam ciklizacionih reakcija za sintezu prekursora nekih fizioloskih vaznih jedinjenja

“…Ges., 1924, 57, 1077 Hallberg, A. J. Org. Chem., 1989, 54, 2964Tihange, G.;Plenevaux, A.;Guillaume, M.;Welter, A.; Dereu, N. Labelled Comp. Radiopharm., 1985, 23, 59.…”