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Hemijska sinteza i biohemijska aktivnost novih derivata 4-hidroksi kumarina

The chemical synthesis and biochemical activities of novel 4-hydroxy coumarin derivatives

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2010
Disertacija.pdf (2.045Mb)
Author
Vuković, Nenad
Mentor
Sukdolak, Slobodan
Committee members
Solujić, Slavica
Vajs, Vlatka
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Abstract
Ova doktorska disertacija je sačinjena iz dve naučne celine. Prvi deo obuhvata hemijsku sintezu derivata 4-hidroksi kumarina, identifikaciju hemijske strukture i hemijske modifikacije uvedenih farmakofora. Druga naučna celina ima za cilj da odgovori kako promena funkcionalnih grupa na osnovnom molekulu 4-hidroksi kumarina utiče na neke oblike biohemijske aktivnosti kao što su antioksidantna aktivnost, antimikrobna aktivnost i antikoagulantna aktivnost. Antioksidantna aktivnost supstrata je određena primenom pet različitih metoda, u cilju definisanja vidova antioksidantne aktivnosti (ukupna antioksidativna aktivnost, antiradikalska aktivnost metodom sa DPPH, reduktivna sposobnost, inhibicija lipidne peroksidacije u prisustvu linoleinske kiseline i OH antiradikalska aktivnost). Na osnovu dobijenih podataka neki od kumarinskih derivata pokazuju veoma jaku antioksidativnu aktivnost. Antimikrobna aktivnost ispitivanih derivata kumarina je određivana kod bakterija i gljiva ...primenom dve metode: makrodilucione i mikrodilucione metode. Dobijeni rezultati su pokazali zavisnost antimikrobne aktivnosti od prirode farmakofore vezane za položaj 3 molekule 4-hidroksi kumarina. Među testiranim kumarinima, amino derivati sa fenil, tolil i p-nitrofenil farmakoforama pokazuju jaku antibakterijsku aktivnost prema bakteriji E. coli. Antikoagulantna aktivnost ispitivanih derivata kumarina je određena modifikovanom metodom po Kviku, a dobijeni rezultati su pokazali da najveću aktivnost ima derivat sa farmakoforom tipa –(CH2)4COOH i u poređenju sa varfarinom i acenokumarolom je efikasniji antikoagulant.

This dissertation includes two scientific wholes. The first whole includes chemical syntheses of 4-hydroxy coumarin derivatives, identification of the chemical structure and chemical modifications of the introduced pharmacophores. The second scientific whole aims to explain how replacement of functional groups on 4-hydroxy coumarin starting compound affect some of the biochemical activities, such as antioxidative, antimicrobial and anticoagulative activities. Antioxidative activity of the compounds was determined using five different methods, in other to define specific kinds of antioxidative activity (total antioxidative activity, antiradical activity by DPPH method, reductive activity,inhibition of lipid peroxidation in linoleic acid and OH antiradical activity). On the basis of obtained data, some of the tested coumarin derivatives showed very good antioxidant activity. Antimicrobial activity of the examined coumarine derivatives was being determined against fungi a...nd bacteria, using two methods- macrodilution and microdilution methods. Obtained results show that antimicrobial activity depends on the kind of the pharmacophore bonded at the 3-position of a 4-hydroxy coumarin compound. Among tested compounds, amino derivatives with phenyl, tolyl and p-nitroohenyl pharmacophores showed strong antibacterial activity against bacteria E. coli. Anticoagulative activity of the examined compounds was determined using a modified Quick`s method, and the obtained results show that the imino derivative with –(CH2)4COOH pharmacophore possesses the strongest activity and is a more efficient anticoagulant than warfarin and acenocoumarol.

Faculty:
Универзитет у Крагујевцу, Природно-математички факултет
Date:
2010
Keywords:
Kumarin / 57
[ Google Scholar ]
Handle
https://hdl.handle.net/21.15107/rcub_nardus_3617
URI
https://nardus.mpn.gov.rs/handle/123456789/3617
http://eteze.kg.ac.rs/application/showtheses?thesesId=1604
https://fedorakg.kg.ac.rs/fedora/get/o:435/bdef:Content/download

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