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Syntheses, Modifications and Biological Applications of Sulfoximines and Aromatic Pentafluorosulfanyl Compounds

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Syntheses, Modifications and Biological Applications of Sulfoximines and Aromatic Pentafluorosulfanyl Compounds Syntheses, Modifications and Biological Applications of Sulfoximines and Aromatic Pentafluorosulfanyl Compounds Von der Fakultät für Mathematik, Informatik und Naturwissenschaften der RWTH Aachen University zur Erlangung des akademischen Grades einer Doktorin der Naturwissenschaften genehmigte Dissertation vorgelegt von Master of Science Christine Maria Margarethe Hendriks, geb. Reucher aus Aachen, Deutschland Berichter: Universitätsprofessor Dr. Carsten Bolm Universitätsprofessor Dr. Dieter Enders Tag der mündlichen Prüfung: 23. November 2015 Diese Dissertation ist auf den Internetseiten der Universitätsbibliothek online verfügbar. The presented work was carried out from March 2012 to September 2015 at the Institute of Organic Chemistry, RWTH Aachen University, under the supervision of Prof. Dr. Carsten Bolm. I would like to thank Prof. Dr. Carsten Bolm for the opportunity to work in his group on challenging and interesting research topics, for his support and the excellent working conditions. Furthermore, I would like to thank my second examiner Prof. Dr. Dieter Enders. Parts of this work have already been published: Bolm, C.; Hendriks, C. M. M.; Lüscher, B.; Hartkamp, J. RWTH Aachen University, Deutsche Patentanmeldung 102016214912.1, 2016. Hendriks, C. M. M.; Penning, T. M.; Zang, T.; Wiemuth, D.; Gründer, S.; Sanhueza, I. A.; Schoenebeck, F.; Bolm, C. Bioorg. Med. Chem. Lett. 2015, 25, 4437–4440. Bizet, V.; Hendriks, C. M. M.; Bolm, C. Chem. Soc. Rev. 2015, 44, 3378–3390. Hendriks, C. M. M.; Nürnberg, P.; Bolm, C. Synthesis 2015, 47, 1190–1194. Hendriks, C. M. M.; Reball, J.; Bolm, C. Synlett 2015, 26, 73–75. Hendriks, C. M. M.; Bohmann, R. A.; Bohlem, M.; Bolm, C. Adv. Synth. Catal. 2014, 356, 1847–1852. Hendriks, C. M. M.; Lamers, P.; Engel, J.; Bolm, C. Adv. Synth. Catal. 2013, 355, 3363–3368. What the elements are to chemistry, what the sounds are to music, are words to language. Ernest Klein To my roots, to my wings Table of Contents Table of Contents 1 Introduction ...................................................................................................................................... 1 1.1 Sulfoximines and Sulfilimines ......................................................................................... 1 1.1.1 Physicochemical properties and applications ......................................... 1 1.1.2 Synthetic routes to sulfoximines and sulfilimines ................................. 2 1.1.3 N-Functionalizations of NH-sulfoximines .............................................. 12 1.1.4 Bioactivities of sulfoximines and sulfilimines ...................................... 15 1.2 Aromatic Pentafluorosulfanyl Compounds ............................................................ 19 1.2.1 Introduction to fluorine and organofluorine compounds ................ 19 1.2.2 Syntheses and derivatizations of pentafluorosulfanyl arenes ....... 20 1.2.3 Properties, applications, and biological activities: pentafluorosulfanyl versus trifluoromethyl .......................................... 21 2 Sulfoxide-to-Sulfilimine Conversions with Modified Burgess-type Reagents ...... 25 2.1 Background and Aim of the Project ........................................................................... 25 2.2 Results and Discussion ................................................................................................... 26 2.3 Summary .............................................................................................................................. 37 3 N-Alkylations of NH-Sulfoximines by Using KOH in DMSO ......................................... 39 3.1 Background and Aim of the Project ........................................................................... 39 3.2 Results and Discussion ................................................................................................... 39 3.3 Summary .............................................................................................................................. 44 4 Syntheses and Biological Activities of Sulfoximine-based ATR Inhibitors ............ 45 4.1 Background and Aim of the Project ........................................................................... 45 4.2 Results and Discussion ................................................................................................... 46 4.2.1 Syntheses of the target compounds .......................................................... 46 4.2.2 Biological tests .................................................................................................. 51 4.3 Summary .............................................................................................................................. 53 5 Synthesis and Biological Activity of a Sulfoximine-Analog of BTB06584, a Mitochondrial F1Fo-ATPase Inhibitor .............................................................................. 55 5.1 Background and Aim of the Project ........................................................................... 55 5.2 Results and Discussion ................................................................................................... 55 5.2.1 Synthesis of the target compound ............................................................. 55 5.2.2 Biological test .................................................................................................... 59 5.3 Summary .............................................................................................................................. 60 Table of Contents 6 Syntheses and Biological Activities of 4-(N-Indolyl)phenyl Methyl Sulfoximines ................................................................................................................................... 61 6.1 Background and Aim of the Project ........................................................................... 61 6.2 Results and Discussion ................................................................................................... 62 6.2.1 Syntheses of the target compounds .......................................................... 62 6.2.2 Biological tests .................................................................................................. 64 6.3 Summary .............................................................................................................................. 65 7 Syntheses of Sulfoximine-Containing Zolimidine Analogs .......................................... 67 7.1 Background and Aim of the Project ........................................................................... 67 7.2 Results and Discussion ................................................................................................... 68 7.2.1 Attempts with sulfilimine and sulfoximine building blocks............ 68 7.2.2 Iminations and oxidations on the imidazo[1,2-α]pyridine- containing backbone ....................................................................................... 69 7.3 Summary .............................................................................................................................. 71 8 Syntheses of Methyl 4-Pentafluorosulfanylphenyl Sulfoximines .............................. 73 8.1 Background and Aim of the Project ........................................................................... 73 8.2 Results and Discussion ................................................................................................... 73 8.3 Summary .............................................................................................................................. 75 9 Syntheses and Biological Activities of Pentafluorosulfanyl-Containing Flufenamic Acid Analogs ........................................................................................................... 77 9.1 Background and Aim of the Project ........................................................................... 77 9.2 Results and Discussion ................................................................................................... 78 9.2.1 Syntheses of the target compounds .......................................................... 78 9.2.2 Computational calculations of structures and properties ............... 78 9.2.3 Biological tests .................................................................................................. 79 9.3 Summary .............................................................................................................................. 82 10 Syntheses of Pentafluorosulfanyl-Containing 1,2,3,4-Tetrahydroquinolines ...... 83 10.1 Background and Aim of the Project ........................................................................... 83 10.2 Results and Discussion ................................................................................................... 84 10.3 Summary .............................................................................................................................. 86 11 Conclusion and Outlook ............................................................................................................. 87 12 Experimental Part ........................................................................................................................ 89 12.1 General Information ........................................................................................................ 89 Table of Contents 12.1.1 Techniques ......................................................................................................... 89 12.1.2 Solvents and chromatography
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