Sinteza i karakterizacija novih amino derivata furostilbena kao potencijalnih inhibitora kolinesteraza

undergraduate thesis

• Title (english): Synthesis and characterization of new amino derivatives of furostilbenes as potential cholinesterase inhibitors
• Author: Petra Kovačec
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Sanja Martinez (član povjerenstva)
• Committee member: Marko Racar (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2020-07-09, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Do danas su provedena mnoga istraživanja usmjerena ka inhibiciji enzima kolinesteraza. Među ranijim primjerima je istraživanje benzilaminskih oksazola koje uključuje njihovu sintezu, izolaciju i karakterizaciju. Ovaj rad svojevrsni je nastavak takvih istraživanja, a provedena je sinteza novih amino derivata tiostilbena. Početni spoj 1 sintetiziran je Wittgovom reakcijom, a daljnje aminacije provedene su Buchwald-Hartwigovom aminacijom. Korišteni su benzilni amini koji su u položaju 3 supstituirani metilnom i metoksi-skupinom, te fluorom i heterociklički furanski i tiofenski amin. Svi su spojevi (2, 3, 4, 5, 6) sintetizirani najprije uz BrettPhos kao ligand, a kasnije su sve reakcije ponovljene s ligandom XPhosom, osim one s metilnim supstituentom čiji su prvotni rezultati bili zadovoljavajući. Svi su spojevi okarakterizirani
1H NMR metodom te je u svim dobivenim uzorcima detektirana očekivana masa masenom spektrometrijom (MS). Ukupna iskorištenja su određena na temelju 1H NMR spektara.

Abstract (english)

To date, many studies have been conducted aimed at inhibiting the enzyme cholinesterases. One of earlier examples is the study of benzylamine oxazoles which includes their synthesis, isolation and characterization. This work is a continuation of such research, and the synthesis of new amino derivatives of thiostilbene deivatives was performed. Initial compound 1 was synthesized by the Wittg reaction, and further aminations were performed by Buchwald-Hartwig amination. Benzyl amines substituted in position 3 by methyl and methoxy group and fluorine. Also heterocyclic furan and thiophene amines were used. All compounds (2, 3, 4, 5, 6) were synthesizedat first with BrettPhos as a ligand, and later all reactions were repeated with the XPhos ligand, except that with a methyl substituent whose initial results were satisfactory. All compounds were characterized by 1H NMR spectroscopy and expected masses were also de-tected my mass spectrometry (MS) in all samples. Overall yields were estimated based on 1H NMR spectra.

• Keywords: amini; Buchwald-Hartwigova aminacija; kolinesteraza; tiostilbeni
• Keywords (english): amines; Buchwald-Hartwig amination; cholinesterase; tiostilbenes
• Language: croatian
• URN:NBN: urn:nbn:hr:149:122896
• Study programme: Title: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-05-04 12:02:11