Sinteza heterocikličnih spojin iz tiosemikarbazidov in študija vezave na cinkove modelne spojine aktivnih mest metaloproteinov

Cizerl, Ana (author), Kljun, Jakob (mentor)

V sklopu svoje diplomske naloge sem optimizirala sintezni poti nastanka 1,2,4-triazolidin-3-tionov in 1,3,4-tiadiazolov. Pri tem sem uspela sintetizirati sedem različnih 1,2,4-triazolidin-3-tionov in tri 1,3,4-tiadiazole. Te spojine so znane po širokem spektru farmacevtskih lastnosti. Izkoristki sintez sicer niso najboljši, ampak to bi verjetno lahko izboljšala z nadaljnjo optimizacijo sinteznih postopkov. Dobljene spojine sem okarakterizirala z NMR, HRMS, elementno analizo; v dveh primerih sem imela primerne kristale za rentgensko strukturno analizo. Namen naloge je bil tudi preučiti način vezave ligandov na modelne cinkove spojine. S pomočjo teh modelnih spojin bi se preučeval način in jakost vezave sintetiziranih molekul v aktivna mesta metaloencimov. Pregledala sem znanstveno literaturo in povzela, kako bi te modelne cinkove spojine lahko sintetizirala.

• Language: Slovenian
• Keywords: sinteza, triazolidin-3-tioni, tiadiazoli, cinkovi modelni kompleksi
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2021
• PID: 20.500.12556/RUL-130156
• COBISS.SI-ID: 83215107
• Publication date in RUL: 10.09.2021

Secondary language

• Language: English
• Title: Synthesis of heterocyclic compounds from thiosemicarbazides and study of their binding to zinc model compounds of metalloprotein active sites

Abstract

As part of my thesis, I optimized the synthetic pathways of 1,2,4-triazolidin-3-thiones and 1,3,4-thiadiazoles. In doing so, I was able to synthesize seven different 1,2,4-triazolidin-3-thiones and three 1,3,4-thiadiazoles. These compounds are known for a wide range of pharmaceutical properties. Although the synthesis yields are not the best, this could probably be improved by further optimizing the synthesis processes. The obtained compounds were characterized by NMR, HRMS and elemental analysis. For two compounds suitable crystals for X-ray structural analysis were obtained. The purpose of the task was to study the method of binding ligands to model zinc compounds. Utilizing these model compounds, the mode and strength of binding of synthesized molecules to active sites of metalloenzymes would be studied. I reviewed the scientific literature and summarized how these compounds could be synthesized.

• Keywords: synthesis, triazolidin-3-thiones, thiadiazoles, zinc model complexes