Aktivacija sililiranih kislinskih derivatov simvastatina za pripravo platinovih(IV) kompleksov s protitumorskim delovanjem

Malenšek, Katja (author), Gazvoda, Martin (mentor)

V okviru diplomskega dela sem simvastatin, ki je lakton, pretvorila v njegov kislinski derivat in na proste OH skupine uvedla sililne zaščitne skupine. Sintetizirala sem aktivirane kislinske derivate dekanojske kisline in simvastatina ter preverjala njihovo zmožnost tvorbe estrov s šibkimi nukleofili. Dekanojsko kislino sem uspešno pretvorila v kislinski klorid in anhidrid, kislinski derivat simvastatina pa v anhidrid. Od naštetih derivatov je le kislinski klorid dekanojske kisline tvoril ester z monosubstituiranimi derivati fenola. Kislinski derivat simvastatina sem uporabila še v reakciji kislinsko katalizirane esterifikacije, ki pa ni vodila do želenega produkta. Po literaturnem postopku mi je uspelo pripraviti Pt(IV)-acetamidato kompleks, ki bi služil kot izhoden Pt(IV) kompleks za nadaljnjo sintezo.

• Language: Slovenian
• Keywords: simvastatin, cisplatin, dekanojska kislina, kislinski kloridi, anhidridi, Pt(IV) kompleksi
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2019
• PID: 20.500.12556/RUL-109936
• COBISS.SI-ID: 1538424259
• Publication date in RUL: 10.09.2019

Secondary language

• Language: English
• Title: Activation of silylated acid derivatives of simvastatin for preparation of platinum(IV) complexes with antitumor activity

Abstract

My bachelor thesis describes the transformation of simvastatin (lactone) into its acid derivative and silylation of its hydroxyl groups. Activated derivatives of decanoic acid and simvastatin were prepared and tested in esterification reactions with soft nucleophiles. Decanoic acid was successfully transformed into acid chloride and anhydride, while only anhydride could be prepared from acid form of simvastatin. Out of all prepared activated acid derivatives only decanoic acid chloride reacted with monosubstituted phenol derivatives. Simvastatin acid derivative was tested in acid catalysed esterification but reaction did not proceed into desired product. Pt(IV)-acetamidato complex was prepared following literature procedures as a starting material for further reactions.

• Keywords: simvastatin, cisplatin, decanoic acid, acid chlorides, anhydrides, Pt(IV) complexes