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A new entry to adenosine analogues via purine nitration - Combinatorial
synthesis of antiprotozoal agents and adenosine receptor ligands
Rodenko, B.
Publication date
2004
Link to publication
Citation for published version (APA):
Rodenko, B. (2004). A new entry to adenosine analogues via purine nitration - Combinatorial
synthesis of antiprotozoal agents and adenosine receptor ligands.
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CONTENTS S CHAPTERR 1 1.1 1 1.2 2 1.3 3 1.4 4 1.5 5 CHAPTERR 2 2.1 1 2.2 2 2.3 3 2.4 4 2.5 5 2.6 6 2.7 7 2.8 8 2.9 9 CHAPTERR 3 3.1 1 3.2 2 3.3 3 3.4 4 3.5 5 3.6 6 3.7 7 CHAPTERR 4 4.1 1 4.2 2 4.3 3 4.4 4 4.5 5 4.6 6 4.7 7 4.8 8 4.9 9 4.10 0 4.11 1 INTRODUCTION N
Solidd phase synthesis and combinatorial chemistry Adenosinee receptors
Nucleosidess as anti-parasitic agents Outlinee of the thesis
References s
S O L I DD P H A S E S Y N T H E S I S O F 2 ^ VÖ
- D I S U B S T I T U T E D A D E N O S I N E A N A L O G U E S
Introduction n
Functionalisingg the purine skeleton Thee nitro group as a leaving group Solidd supported syntheses Libraryy synthesis
Concludingg remarks Acknowledgements s Experimental l References s
SOLIDD PHASE SYNTHESIS OF DI- AND TRISUBSTITUTED 5'-CARBOXAMIDO-ADENOSINEE ANALOGUES
Introduction n
Solidd phase syntheses with Kenner's sulfonamide linker Solidd phase syntheses with the hydrazide linker
Concludingg remarks Acknowledgements s Experimental l References s
CONFORMATIONN ALLY RESTRICTED ADENOSINE ANALOGUES
Introduction n
Syntheticc approach towards 2,N6 tethered adenosine analogues Macrocycless derived from symmetrical diamines
Macrocycless derived from asymmetrical diamines 'Open'' 2,6 disubstituted analogues
2,5'' -Tethered adenosine analogues Bindingg studies at the adenosine receptors Concludingg remarks Acknowledgements s Experimental l References s 2 2 4 4 13 3 24 4 24 4 30 0 30 0 32 2 32 2 37 7 37 7 37 7 39 9 43 3 46 6 49 9 51 1 57 7 57 7 57 7 64 4 68 8 71 1 72 2 74 4 77 7 78 8 82 2 84 4 84 4 84 4 95 5
CHAPTERR 5 ANTIPROTOZOAL EVALUATION OF ADENOSINE ANALOGUES 5.11 Introduction 5.22 Antiprotozoal screening 5.33 Concluding remarks 5.44 Acknowledgements 5.55 Experimental 5.66 References 98 8 98 8 107 7 107 7 107 7 111 1
CHAPTERR 6 THE MECHANISM OF PURINE NITRATION
6.11 Introduction
6.22 Trifluoroacetyl nitrate in purine nitration reactions 6.33 Proposed mechanisms
6.44 Detection of a 7-nitro-8-trif~luoroacetoxy purine intermediate 6.55 The N-nitration-nitramine rearrangement mechanism 6.66 Chemically Induced Dynamic Nuclear Polarisation (CIDNP) 6.77 Side products: 8-oxo purine formation
6.88 Concluding remarks 6.99 Acknowledgements 6.100 Experimental 6.111 References 114 4 115 5 116 6 118 8 121 1 126 6 132 2 133 3 134 4 134 4 138 8 SUMMARY Y 141 1 SAMENVATTING G 145 5 NAWOORD D 149 9 vin n
