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Synthesis of Glucose Conjugates with Pyridinium Aldoximes as Antidotes against Organophosphate Poisoning


Baumann, Krešimir; Brglez, Josipa; Štimac, Adela; Primožič, Ines; Tomić, Srđanka
Synthesis of Glucose Conjugates with Pyridinium Aldoximes as Antidotes against Organophosphate Poisoning // XXI Hrvatski skup kemičara i kemijskih inženjera, Knjiga sažetaka. / Novak, Predrag (ur.).
Kutina: Hrvatsko društvo kemijskih inženjera i tehnologa, 2009. str. 57-57 (poster, domaća recenzija, sažetak, znanstveni)


Naslov
Synthesis of Glucose Conjugates with Pyridinium Aldoximes as Antidotes against Organophosphate Poisoning

Autori
Baumann, Krešimir ; Brglez, Josipa ; Štimac, Adela ; Primožič, Ines ; Tomić, Srđanka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
XXI Hrvatski skup kemičara i kemijskih inženjera, Knjiga sažetaka. / Novak, Predrag - Kutina : Hrvatsko društvo kemijskih inženjera i tehnologa, 2009, 57-57

ISBN
978-953-6894-38-3

Skup
XXI. hrvatski skup kemičara i kemijskih inženjera

Mjesto i datum
Trogir, Hrvatska, 19.- 22.04.2009

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
Antidotes against organophosphorus poisoning; synthesis; pyridinium aldoximes; glucose conjugates

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
119-1191344-3121 - Sinteze i enzimske transformacije biološki aktivnih spojeva (Srđanka Tomić-Pisarović, )

Ustanove
Prirodoslovno-matematički fakultet, Zagreb