Amino- i nitro-supstituirani benzo[b]tieno[2,3-c]kinoloni kao potencijalni antioksidansi

undergraduate thesis

• Title (english): Amino- and nitro-substituted benzo[b]thieno[2,3-c]quinolones as potential antioxidants
• Author: Angela Kapitanović
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Maja Cindrić (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2017-09-15, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

okviru ovog rada priređeni su amino i nitro supstituirani derivati benzo[b]tieno[2,3-c]kinolona. Za pripravu ciljanih molekula korištene su klasične metode organske sinteze. Počevši od sinteze cimetnih kiselina 3a-b koje se prevode u odgovarajuće kloride 4a-b te njihovom kondenzacijom s anilinima dobivaju se nitro supstituirani amidi 6-8. Redukcijom nitro skupine spojeva 6-8 dobivaju se amino supstituirani amidi 12-14. Sinteza cikličkih derivata 9-11 i 15-17 provedena je fotokemijskom ciklizacijom acikličkih spojeva 6-8 te 12-14. Struktura priređenih spojeva potvrđena je korištenjem 1H i 13C NMR spektroskopije. Spojevi su dodatno spektroskopski okarakterizirani UV/Vid i fluorimetrijskom spektroskopijom, a provedene su i UV/Vid i fluorimetrijske titracije otopina spojeva s različitim otopinama metalnih soli ili u puferima različitog pH kako bi se utvrdila njihova mogućnost primjene kao senzora za određivanje kationa u otopinama ili za detekciju pH. Nekim priređenim derivatima ispitana je i antioksidativna aktivnost.

Abstract (english)

In this work, we describe the synthesis of novel amino and nitro substituted derivates of benzo[b]thieno[2,3-c]quinolones. For the preparation of target molecules classical methods of organic synthesis were used started from cimetic acids 3a-b which are converted to corresponding acyl-chlorides 4a-b which gave in the condensation with anilines targeted nitro substituted amides 6-8. Within the reduction of nitro derivatives 6-8, amino substituted amides 12-14 obtained. Cyclic derivatives 9-11 and 15-17 were prepared by using photochemical cyclization of acyclic molecules 6-8 and 12-14. The structure of synthesized molecules were confirmed by means of 1H i 13C NMR spectroscopy. Also, the synthesized molecules were additionally studied by UV/Vis and fluorimetric spectroscopy. Also, UV/Vis and fluorimetric titrations of aqueous compounds solutions with aqueous solutions of metal salts or with buffers with different pH were performed to explore their possible application as chemosensors or pH sensors. Some of prepared derivatives were tested for their antioxidative activity.

• Keywords: amidi; benzo[b]tieno[2 3-c]kinoloni; UV/Vid; fluorimetrijska i NMR spektroskopija; kemijski senzori; pH senzori; antioksidativna aktivnost
• Keywords (english): amides; benzo[b]thieno[2 3-c]quinolones; UV/Vis; fluorimetric and NMR spectroscopy; chemosensors; pH sensors; antioxidative activity
• Language: croatian
• URN:NBN: urn:nbn:hr:149:636105
• Study programme: Title: Chemical Engineering - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2021-03-12 09:27:50