Synthesis of Glucose Conjugates with Pyridinium Aldoximes as Antidotes against Organophosphate Poisoning (CROSBI ID 549212)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | domaća recenzija
Podaci o odgovornosti
Baumann, Krešimir ; Brglez, Josipa ; Štimac, Adela ; Primožič, Ines ; Tomić, Srđanka
engleski
Synthesis of Glucose Conjugates with Pyridinium Aldoximes as Antidotes against Organophosphate Poisoning
In the attempt to improve the quality of antidotes against organophosphorus poisoning, pyridinium aldoxime reactivators of inhibited acetylcholinesterase were linked to the sugar moiety.1 It was found that the attachment of a sugar group to the oxime derivative increases the bioavailability of the antidote and the antidote is retained longer in the blood circulation. Moreover, the sugar analogs are usually less toxic than the non-sugar analogs ; some also displayed higher efficacy.1, 2 A series of pyridine 2-, 3- and 4-aldoximes having a glucose conjugated to the pyridine ring have been prepared. The sugar residue was attached through ethano or propano bivalent bridge between the glycosyl hydroxyl group and the nitrogen atom of the pyridinium moiety. Several synthetic routes were investigated and the best approach was determined. In the first step, the reaction of penta-O-acetyl-ß-D- glucopyranose with 2-bromoethanol or 3- bromopropanol was carried out to obtain 2- or 3- bromoalkyl-2, 3, 4, 6-tetra-O-acetyl-ß-D- glucopyranosides (catalyst BF3 Et2O ). In the next step, acetyl groups were removed with dibutyltin oxide and 2- or 3-bromoalkyl-ß-D- glucopyranosides were obtained. Quaternization of 2- and 3- bromoalkyl-ß-D-glucopyranosides with appropriate pyridine aldoxime resulted in the desired pyridinium glucoconjugates. The structures of compounds were deduced from IR, one- (1H, 13C broadband decoupling and APT) and two-dimensional NMR (H, H-COSY, NOESY and HETCOR) spectra. Prepared compounds will be further investigated as inhibitors and reactivators of acetylcholinesterase inhibited with organophosphorus compounds. The structural requirements in relation to the sugar attachment to the oxime function will be discussed.
antidotes against organophosphorus poisoning ; synthesis ; pyridinium aldoximes ; glucose conjugates
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
Podaci o prilogu
57-57.
2009.
objavljeno
Podaci o matičnoj publikaciji
XXI. hrvatski skup kemičara i kemijskih inženjera, Knjiga sažetaka.
Novak, Predrag
Zagreb: Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI)
978-953-6894-38-3
Podaci o skupu
XXI. Hrvatski skup kemičara i kemijskih inženjera
poster
19.07.2009-22.07.2009
Trogir, Hrvatska