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200225128.Pdf Members of the Examination Committee: Prof. Dr. ir. Nico Boon (Chairman) Department of Biotechnology, Faculty of Bioscience Engineering, Ghent University Prof. Dr. Adrian Dobbs Department of Pharmaceutical, Chemical and Environmental Sciences, Faculty of Engineering and Science, University of Greenwich Dr. Steven De Jonghe Laboratory of Virology and Chemotherapy, Rega Institute for Medical Research, KU Leuven Prof. Dr. Serge Van Calenbergh Laboratory of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ghent University Prof. Dr. ir. Matthias D’hooghe Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University Prof. Dr. ir. Marjan De Mey Department of Biotechnology, Faculty of Bioscience Engineering, Ghent University This work was supported by the Agency for Innovation by Science and Technology, Flanders (IWT- SBO project 100014) and the Special Research Fund (BOF project BOF14/DC1/032) Promotor: Prof. Dr. ir. Christian Stevens Department of Green Chemistry and Technology Faculty of Bioscience Engineering Ghent University Dean: Prof. Dr. ir. Marc Van Meirvenne Rector: Prof. Dr. ir. Rik Van de Walle Faculty of Bioscience Engineering 2019 ir. Laurens De Coen Synthesis and Preliminary Biological Evaluation of Furo- and Oxazolopyrimidine Analogues Thesis submitted in fulfilment of the requirements for the degree of Doctor (PhD) in Applied Biological Sciences: Chemistry and Bioprocess Technology Dutch translation of the title: Synthese en preliminaire biologische evaluatie van furo- en oxazolopyrimidines Please cite as: De Coen, L.; ‘Synthesis and Preliminary Biological Evaluation of Furo- and Oxazolopyrimidine Analogues’, PhD Dissertation, Ghent University, 2019 Cover illustration: Exploring Chemical Space (Laurens De Coen) ISBN number: 9789463572064 The author and the promotor give authorization to consult and copy parts of this work for personal use only. Every other use is subject to copyright laws. Permission to reproduce any material contained in this work should be obtained from the author. Ghent, May 2019 The author, The promotor, ir. Laurens De Coen Prof. Dr. ir. Christian Stevens Woord vooraf Met het schrijven van dit voorwoord komt er een einde aan mijn avontuur bij de Universiteit Gent, en kan ik terugkijken op een mooi hoofdstuk in mijn leven. In dit voorwoord zal ik het verloop van mijn traject aan de universiteit wat toelichten, en de mensen bedanken die hun bijdrage hebben geleverd aan deze thesis. Het begon allemaal met de keuze om na mijn middelbare studies aan een opleiding tot bio-ingenieur te beginnen aan de Universiteit Gent. De grote hervorming van de bachelor/master-structuur was toen net achter de rug, en de opleiding ging van start met een algemene basis. Daarna kon ik mijn eigen richting bepalen met de keuze van een afstudeerrichting en de samenstelling van keuzevakken. Aan de richting die ik wou uitgaan binnen de opleiding tot bio-ingenieur heb ik eigenlijk nooit getwijfeld. Ik heb altijd een passie gehad voor chemie, en de Master in ‘Chemie en Bioprocestechnologie’ klonk dan ook als muziek in mijn oren. In het laatste jaar begon ik aan een Masterthesis binnen de vakgroep Duurzame Organische Chemie en Technologie onder het promotorschap van professor Stevens. Tijdens mijn thesis deed ik onderzoek naar de synthese van analogen van het natuurproduct zingeron met potentiële antikankereigenschappen. Ik kijk nog steeds met fierheid terug op mijn Masterthesis. Na mijn Masteropleiding kon ik instappen in een medicinaal IWT-SBO doctoraatsproject dat iets meer dan een jaar eerder van start was gegaan. Een doctoraatsstudent had na een jaar de overstap gemaakt naar een job in de farmaceutische industrie, en ik kon zijn positie overnemen. Dit betekende meteen ook dat ik minder dan drie jaar financiering had. Extra financiële middelen werden uiteindelijk bekomen na het schrijven en succesvol behalen van een BOF-project, waardoor ik uiteindelijk 3 jaar en 10 maanden officieel betaald werd om aan mijn doctoraat te werken. Tijdens deze periode heb ik mij met allerlei projecten beziggehouden. Zo waren er syntheseprojecten voor Galapagos, UZ Gent en VIB. Steeds nam ik enthousiast deze opdrachten aan, en allen resulteerden uiteindelijk in succes. Mede daardoor vond ik na iets minder dan vier jaar dat de resultaten van mijn eigen doctoraatsproject nog niet volstonden om te doctoreren, alhoewel technisch gezien aan de criteria voldaan werd. De mogelijkheid die zich toen aanbood was om als wetenschappelijk medewerker fulltime op onderzoeksprojecten te werken, en daar bovenop het doctoraatswerk af te ronden. Dit bleek uiteindelijk niet zo evident. Ik wou namelijk van deze onderzoeksprojecten ook een succes maken, en dit vereiste een grote inzet. Wat volgde waren onderzoeksprojecten voor Cargill, Creachem en een consortium van bedrijven in het ATOM-2 project, hetgeen resulteerde in een verbreding van mijn chemische expertise, en een aantal mooie onderzoeksrapporten. Uiteindelijk slaagde ik er ook in om mijn doctoraatsthesis af te ronden, na het opofferen van veel vrije tijd en vakantiedagen. Met het schrijven van deze tekst is het einde van mijn doctoraatsproject eindelijk nabij. Tijdens mijn periode aan de universiteit heb ik heel veel verschillende mensen leren kennen. Zowel op het werk als naast het werk heb ik met deze mensen fijne momenten beleefd, maar het zou mij veel te ver leiden om al deze anekdotes hier neer te pennen. Een doctoraat is niet enkel een persoonlijk project, het is ook teamwerk. Zonder de hulp van andere mensen zou het absoluut onmogelijk geweest zijn om dit te verwezenlijken. Eerst en vooral wil ik professor Stevens bedanken, om mij steeds kansen te bieden en voor het vertrouwen dat u mij hebt geschonken. Ik heb steeds veel vrijheid gekregen om als wetenschapper mijn eigen weg te zoeken in alle projecten, waarvoor dank. Daarnaast stond uw deur steeds open om met vragen of problemen langs te komen. Ten tweede wil ik Bart bedanken. Telkens als ik raad of hulp nodig had, stond je klaar om te helpen. Je hebt me geholpen met mijn Masterthesis, met het BOF-project, bij het schrijven en publiceren van wetenschappelijke artikels en met zovele andere zaken… steeds kon ik op jou rekenen. Bedankt! Daarnaast wil ik ook alle andere collega’s, vrienden en familieleden bedanken voor hun hulp en voor alle toffe momenten. I would also like to thank Prof. Nico Boon, Prof. Adrian Dobbs, Dr. Steven De Jonghe, Prof. Serge Van Calenbergh, Prof. Matthias D’hooghe and Prof. Marjan De Mey for being part of the examination committee. Your thorough reading of the manuscript and your comments and suggestions improved the quality of this thesis, which I highly appreciate. De mensen die mijn moleculen hebben onderzocht op biologische activiteit hebben ook een grote bijdrage geleverd aan dit werk. Bij deze wil ik Prof. Naesens, Prof. Coenye en Prof. Müller bedanken voor al hun biologische resultaten. Ten slotte wil ik Marine bedanken, mijn hartendiefje, voor alle steun, voor de vele mooie dingen die we samen beleefd hebben, om er te zijn voor mij, voor alles. Ես քեզ սիրում եմ բեբի ! Laurens De Coen Mei 2019 Table of contents Introduction and goals ........................................................................................................................1 Literature overview.............................................................................................................................5 1 Synthesis and biological activity of furo[3,4-d]pyrimidines .......................................................5 1.1 Synthesis of furo[3,4-d]pyrimidines .................................................................................5 1.2 Biological activity .............................................................................................................8 2 Synthesis and biological activity of 5,7-dihydrofuro[3,4-d]pyrimidines .....................................9 2.1 Synthesis of 5,7-dihydrofuro[3,4-d]pyrimidines ...............................................................9 2.2 Biological activity ........................................................................................................... 13 3 Synthesis and biological activity of oxazolo[4,5-d]pyrimidines ............................................... 15 3.1 Synthesis of oxazolo[4,5-d]pyrimidines .......................................................................... 15 3.2 Biological activity ........................................................................................................... 19 4 Synthesis and biological activity of oxazolo[5,4-d]pyrimidines ............................................... 20 4.1 Synthesis of oxazolo[5,4-d]pyrimidines .......................................................................... 20 4.2 Biological activity ........................................................................................................... 35 5 Conclusions ........................................................................................................................... 39 Results and discussion ...................................................................................................................... 41 1 Synthesis of furo[3,4-d]pyrimidine analogues ........................................................................ 41 1.1 Synthesis of the furo[3,4-d]pyrimidine-2,4-dione scaffold and subsequent reaction with phosphorus oxychloride ...........................................................................................................
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