Skip to main content
Home
About repository
Contact
EN
HR
Unversity of Zagreb Repository
Browse
By Author
By Year
By Organizational unit
By Scientific field
By Object type
By repositories
All documents
Advanced search
Upload
Search Term
Download
PDF 1.25 MB
undergraduate thesis
1
0
The novel 7-deazapurine derivatives: organometallic synthesis and structural characterization
Petra Orehovački (2015)
University of Zagreb
Faculty of Chemical Engineering and Technology
Cite this item:
https://urn.nsk.hr/urn:nbn:hr:149:701141
Metadata
Title
Novi derivati 7-deazapurina: organometalna sinteza i strukturna karakterizacija
Author
Petra Orehovački
Mentor(s)
Tatjana Gazivoda Kraljević
(thesis advisor)
Abstract
Cilj ovog rada bio je sintetizirati nove N-1 triazolilne i C-5 alkinilne derivate citozina i 7-deazapurina, u svrhu ispitivanja njihove antitumorske aktivnosti protiv tumorskih staničnih linija porijeklom iz čovjeka (Raji, K564, HeLa, CaCo-2). Reakcijom jodiranja N-4-benzoilcitozina pripravljen je N-4-benzoil-5-jodcitozin (1) koji je podvrgnut reakciji N-alkiliranja s propargil-bromidom i NaH kao bazom te je dobiven N-1 alkinilni derivat citozina 2. „Click“ reakcijom kataliziranom bakrom N-1 propargiliranog citozinskog derivata 2 s različito supstituiranim azidima dobiveni su N-1-triazolilni derivati N-4-benzoil-5-jodcitozina (3–5). Sonogashira-inom reakcijom unakrsnog spajanja spojeva 4 i 5 s odgovarajućim terminalnim alkinima, sintetizirani su C-5 alkinilni derivati N-4-benzoil-N-1-triazolilcitozina 6 i 8. 5-endo-dig ciklizacijom in situ spojeva 6 i 8 pripravljeni su C-6 supstituirani derivati 7-deazapurina 7 i 9. Strukture novosintetiziranih spojeva potvrđene su 1H NMR spektroskopijom.
Keywords
cytosine
7-deazapurine
N-alkylation
„click“ reaction
Sonogashira reaction
Parallel title (English)
The novel 7-deazapurine derivatives: organometallic synthesis and structural characterization
Committee Members
Tatjana Gazivoda Kraljević
(committee chairperson)
Maja Stipković Babić
(committee member)
Lidija Furač
(committee member)
Granter
University of Zagreb
Faculty of Chemical Engineering and Technology
Place
Zagreb
State
Croatia
Scientific field, discipline, subdiscipline
NATURAL SCIENCES
Chemistry
Organic Chemistry
Study programme type
university
Study level
undergraduate
Study programme
Environmental Engineering - Undergraduate study
Academic title abbreviation
univ. bacc. ing. oecoing.
Genre
undergraduate thesis
Language
Croatian
Defense date
2015-09-08
Parallel abstract (English)
The aim of this study was to synthesize the novel N-1 triazolyl and C-5 alkynylated pyrimidine and 7-deazapurine derivatives in order to evaluate their antitumor activities against human malignant tumor cell lines (Raji, K562, HeLa, CaCo-2). N-4-benzoyl-5-iodocytosine (1) was prepared by iodination reaction of N-4-benzoylcytosine which was then subjected to N-alkylation reaction with propargylbromide in the presence of NaH as base to give N-alkynylated cytosine derivative 2. N-1-triazolyl derivatives of N-4-benzoyl-5-iodocytosine (3–5) were obtained via copper catalysed „click“ reaction of N-1-propargylcytosine derivative 2 with corresponding azides. Sonogashira cross-coupling reaction of compounds 4 and 5 with corresponding terminal alkynes gave C-5 alkynylated derivates of N-4-benzoyl-N-1-triazolylcytosine 6 and 8. 7-deazapurine derivatives 7 and 9 were prepared by in situ 5-endo-dig cyclization of the compounds 6 and 8, respectively. The structures of newly synthesized compounds were determined by 1H NMR spectroscopy.
Parallel keywords (Croatian)
citozin
7-deazapurin
N-alkiliranje
„click“ reakcija
Sonogashira-ina reakcija
Resource type
text
Access condition
Open access
Terms of use
URN:NBN
https://urn.nsk.hr/urn:nbn:hr:149:701141
Committer
Goran Galinec