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Design, synthesis and characterisation of Cinchona alkaloid carbamates


Ramić, Alma; Matošević, Ana; Bosak, Anita; Kovarik, Zrinka; Hrenar, Tomica; Primožič, Ines
Design, synthesis and characterisation of Cinchona alkaloid carbamates // 26. hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem, 4. simpozij "Vladimir Prelog", Šibenik, Knjiga sažetaka / Galić, Nives ; Rogošić, Marko (ur.).
Šibenik, Hrvatska, 2019. str. 61-61 (poster, domaća recenzija, sažetak, znanstveni)


Naslov
Design, synthesis and characterisation of Cinchona alkaloid carbamates

Autori
Ramić, Alma ; Matošević, Ana ; Bosak, Anita ; Kovarik, Zrinka ; Hrenar, Tomica ; Primožič, Ines

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

Izvornik
26. hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem, 4. simpozij "Vladimir Prelog", Šibenik, Knjiga sažetaka / Galić, Nives ; Rogošić, Marko - , 2019, 61-61

ISBN
978-953-6894-67-3

Skup
26. hrvatski skup kemičara i kemijskih inženjera, 4.simpozij "Vladimir Prelog"

Mjesto i datum
Šibenik, Hrvatska, 9.-12.04.2019.

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
Chinchona alkaloid, carbamates, acetylcholinesterase, butyrylcholinesterase

Sažetak
Cinchona alkaloids and their derivatives are useful in organic chemistry as organocatalysts in stereoselective syntheses, but due to their various bioactive properties they are also very important in medicinal chemistry. To investigate a new class of potentially bioactive Cinchona alkaloids, a series of mono‐ and disubstituted aliphatic (methyl, ethyl and cyclohexyl groups) and mono‐ and disubstituted aromatic (phenyl groups) cinchonine carbamates and their corresponding pseudo‐ enantiomeric cinchonidine carbamates have been prepared and characterized. Structural properties of prepared compounds were studied by FT‐IR, 1D and 2D 1H and 13C NMR spectroscopy. Since some derivatives of cinchonidine have been previously identified as inhibitors of cholinesterases, [1, 2] all prepared carbamate derivatives were screened for their ability to inhibit human acetylcholinesterase and butyrylcholinesterase activity. To explain the differences of the determined carbamylation rates of pseudo‐ enantiomeric carbamates, quantum chemical calculation were used to determine transition states of the carbamylation reaction. Full conformational analysis was performed for all compounds and multi‐way methods were used to correlate inhibition activities with theoretical results. Synthesis, physicochemical characterisation and classification model build by principal component analysis for all compounds will be discussed.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti, Farmacija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2016-06-3775 - Aktivnošću i in silico usmjeren dizajn malih bioaktivnih molekula (Tomica Hrenar, )
HRZZ-IP-2018-01-7683 - Analiza interakcija butirilkolinesteraze s novim inhibitorima i reaktivatorima (Zrinka Kovarik, )

Ustanove
Institut za medicinska istraživanja i medicinu rada, Zagreb,
Prirodoslovno-matematički fakultet, Zagreb