Priprava N,O-acetalnih derivata izoindolinona s prirodnim alkoholima

master's thesis

• Title (english): Synthesis of isoindolinone-derived N,O-acetals with natural alcohols
• Author: Kristina Čikulin
• Mentor: Matija Gredičak (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Tajana Begović (član povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Željka Car (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2023-02-21, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U radu je prikazana priprava N,O-acetalnih derivata izoindolinona, u kojima su izvor eterske
komponente bili prirodni alkoholi, poput borneola, 1-tetradekanola i izopropilidenima zaštićeni
derivat galaktoze. Istraživanja su pokazala da su N,O-acetali važni strukturni motivi i sintetski
intermedijeri raznim prirodnim spojevim i farmaceutskim lijekovima. Također, izoindolinonski
derivati N,O-acetala poznati su inhibitori MDM2-p53 protein-protein interakcija. U prvoj fazi
ovog istraživačkog rada pripremljeni su 3-supstituirani-3-hidroksiizoindolinoni adicijom
Grignardovog reagensa, reakcijom izmjene halogen-litij. Na pripravljenim spojevima uvedena
je N,O-acetalna podjedinica korištenjem serije primarnih i sekundarnih alkohola kao nukleofila.

Abstract (english)

The preparation of N,O-acetal-derived isoindolinones is described, in which the source of the
ether component are natural alcohols, such as borneol, 1-tetradecanol, and isopropylidene
protected derivatives of galactose. Research has shown that N,O-acetals are important structural
motifs and synthetic intermediates in various natural compounds and commercially available
drugs. Isoindolinone N,O-acetal derivatives are known inhibitors of MDM2-p53 protein-protein
interactions. In the first phase of this work, 3-substituted-3-hydroxyisoindolinones were
prepared by addition of Grignard reagent, halogen-lithium exchange reaction. The N,O-acetal
subunit was introduced into the prepared compounds using a series of primary and secondary
alcohols as nucleophiles.

• Keywords: N; O-acetal; kvaterni centar; prirodni alkohol; 3-supstituirani-3-hidroksiizoindolinoni
• Keywords (english): N; O-acetal; quaternary center; natural alcohol; 3-substituted-3-hydroxyisoindolinone
• Language: croatian
• URN:NBN: urn:nbn:hr:217:256501
• Project: Number: IP-2018-01-4053; Title: Nove strategije za pripravu tetrasupstituiranih kiralnih centara: asimetrične katalitičke reakcije usmjerene protuanionom; Acronym: NSYNC-ACDC; Leader: Matija Gredičak; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2025-02-21
• Created on: 2023-03-31 11:44:10