Synthesis of 2-substituted β-cyclodextrin derivatives with a hydrolytic activity against the organophosphorylester paraoxon

Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

“…For both studied concentrations (0.25 and 0.5 mM), the catalysts 1 – 3 were poisoned by the formed p -nitrophenol after a determined time. This phenomenon was already observed: the inclusion of the hydrolysis product in the cyclodextrin cavity limits the catalyst regeneration [27]. …”

Improved access to 2-O-monobenzyl ethers of β-cyclodextrin as precursors of catalysts for organophosphoryl esters hydrolysis

“…After filtration, the solid residue was chromatographed on silica gel (12:7:4, EtOAc-isopropanol-water) yielding 1 (1.15 g, 23.5%, yellow solid); mp >260°C; ½a 20 D +107 (c 1.05, water), ESIMS and NMR-spectra were in agreement with the published data. 2 …”

“…With the base/solvent system sodium hydroxide in dimethyl sulfoxide, monosubstitution at O-2 was achieved but with a low 16% yield. 2 In order to obtain larger amounts of 2 for kinetic and detoxification studies, it was necessary to improve the synthesis of 1. In the present study, we investigated various approaches for the monosubstitution by benzyl groups at O-2, using several base/solvent systems (Scheme 2, Table 1) and differently substituted benzyl halides (Scheme 3, Table 2).…”

“…1 Recently, functionalized cyclomaltoheptaose (b-CD) derivatives bearing the 2-iodosobenzoic acid functionality were developed as artificial enzymes to scavange and hydrolyze neurotoxic organophosphorus (OP) molecules. 2 This catalytic group is known to react as an anionic nucleophile active against various OPs, 3 showing potential to detoxify OP agents. An improved activity against diethyl 4-nitrophenyl phosphate (paraoxon) was achieved using 2 I -O-(3-carboxy-4-iodoso)benzyl-cyclomaltoheptaose 2.…”

Cyclodextrin derivatives that display Enzyme Catalysis

“…5) and its 3 aromatic regioisomers have been found to catalyze hydrolysis of the phosphate ester paraoxon (diethyl pnitrophenyl phosphate) in an enzyme-like manner. Compound 24 was the best catalyst among these isomers (35).…”