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Book of abstracts SPOC 2018 Synthesis of a terpyridine ligand used in photodynamic treatment Author Harmen Spakman Academy of Technology for Health and Environment Avans Hogeschool, Breda University of Leiden terpyridine ligand used in photodynamic treatment Abstract This project consists in the synthesis of a functional terpyridine derivate that could be part of active Ruthenium complex used in photodynamic treatment for it’s phototoxic activity used in tumor targeting. In which this Ruthenium complex in the form of [Ru(tpy)(bpy)Cl] 2+ will selectively destroy cancerous DNA. The synthesis path follows a reaction path consisting of a Claisen condensation of Acetone and Ethylpyridine-2-carboxylate in presence of sodium ethoxide as a base followed by a Krӧnke pyridine synthesis in which a ring closing reaction will occur in the presence of Ammonium acetate shown in figure 1. This path could show an alternative to conventionally used research paths which are widely used [1][2].Goal in this project will be to record a significant yield in the overall reaction over previous studies conducted at Avans Hogeschool. Products will be characterized by FTIR, NMR, TLC, Yield and the melting point will be determined. Further research could be conducted at Leiden University. Keywords: Synthesis, Claisencondesation, Krӧnke pyridine synthesis, Terpyridine, Terpyridine derivated, PDT Table of content Figure 1: Reaction scheme of followed reactions to complete the synthesis of the final terpyridine derivate. [1] M. C. Thompson, „The synthesis of 2,2':6',2"-terpyridine ligands - versatile,” Coordination Chemistry Reviews, School of Chemistry, University of Bristol, Cantock s Close, Bristol, BS8 1TS, UK, 1997 . [2] Synthesis and Adsorption Properties, Toward Some Heavy Metal Ions, of a New Polystyrene-Based Terpyridine Polymer Department of Chemistry, The University of Jordan, Amman 11942, Jordan2Laboratory of Applied Biochemistry, Department of Biology, Faculty of Sciences, University Ferhat Abbas, Setif 19000, Algeria 66
Synthesis of a terpyridine ligand for the application in photodynamic therapy Author terpyrdine Timo van Veen ligand for the application in photodynamic therapy Academy of Technology for Health and Environment Avans Hogeschool, Breda University of Leiden Abstract Worldwide is cancer one of the biggest causes of death [1]. A relatively new cure for cancer is called “Photo dynamic therapy”. In comparison with chemotherapy, photo dynamic therapy is an easier medication method for the patient. For this therapy a photo dynamic medicine is needed. The goal of this research is to synthesize this photo dynamic medicine, the ligand [2,2’:6,2”- terpyridine]-4’-ylmethanol. This ligand is shown in Figure 1. This ligand is able to form a complex with ruthenium. When a laser is applied on this complex it will become toxic for the tumour [2] . To synthesize this ligand a 4 step synthesis is carried out. This reaction equation is shown in Figure 2. The first step is a reaction known as the furan pathway, with acetyl pyridine and furfural under basic conditions to form 4’-(Furan-2-yl)-2,2’:6’,2”-terpyridine. Step 2 is an oxidation with KMnO4 to synthesize [2,2':6',2''-terpyridine]-carboxylic acid. Next there will be a Fischer esterification to synthesize (Methyl)-2,2':6',2''-Terpyridine-4'-carboxylate. The final step is to reduce the ester product towards the goal molecule [2,2’:6,2”- terpyridine]-4’-ylmethanol by using NaBH4 [3] . All obtained products are purified by recrystallization and analysed by FTIR and 1 H-NMR. Keywords: Photo dynamic therapy, Terpyridine derivative, The furan pathway Table of content Figure 1: The goal molecule. Figure 2: Overall reaction equation [1] L. Torre, F. Bray, R. Siegel, J. Ferlay, J. Lortet-Tieulent en A. Jemal, „Global cancer statistics 2012,” Cancer Journal, nr. 65, pp. 87-108, 2015. [2] V. Brabec en O. Nováková, „DNA binding mode of ruthenium complexes and relationship to tumor cell toxicity,” Drug Resistance Updates, nr. 9, pp. 111-122, 2006. [3] M. Heller en U. S. Schubert, „Functionalized 2,2′-Bipyridines and 2,2′:6′,2′′-Terpyridines via Stille-Type Cross-Coupling Procedures,” Journal of inorganic chemistry, pp. 8269 -8272, 2002. 67
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Book of Abstracts Poster presentati
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Avans University of Applied Science
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Collaborations 5
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Preface Dear reader, We present her
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Index SPOC1 13 Tutor: Nishant Sewgo
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Group index SPOC1 The inhibition of
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The inhibition of the Pseudomonas A
Page 15 and 16: Synthesis of a surface-active RAFT-
Page 17 and 18: Synthesis for a building block for
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Page 21 and 22: Group index SPOC2 In situ catalysed
Page 23 and 24: Book of abstracts SPOC 2018 3,4-uns
Page 25 and 26: Determination of activation energie
Page 27 and 28: Book of abstracts SPOC 2018 Synthes
Page 29 and 30: Group index SPOC3 Decarboxylation o
Page 31 and 32: Decarboxylation of ferulic acid to
Page 37 and 38: Group index SPOC4 The kinetics of t
Page 39 and 40: The kinetics of the Knoevenagel con
Page 41 and 42: Isolation of catalytic intermediate
Page 43 and 44: Chemical recycling to Oxazolines Au
Page 45 and 46: Group index SPOC5 Molecular Imprint
Page 47 and 48: Taxus extract Molecular Imprinted P
Page 49 and 50: MIP synthesis of 4-vinylpyridine Au
Page 51 and 52: Biobased Block-Copolymers due ATRP
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Page 55 and 56: Group index SPOC6 Synthesis of Beta
Page 57 and 58: Synthesis of Beta-lactam in three s
Page 59 and 60: Isoxazoline ring opening by TBAT to
Page 61 and 62: Synthesis of a ligand for a synthet
Page 63 and 64: Group index SPOC7 Synthesis of a te
Page 65: Book of abstracts SPOC 2018 Synthes
Page 69 and 70: Synthesis of peptides for IR foldin
Page 71 and 72: Peptide synthesis for unravelling p
Page 73 and 74: Dear reader, Acknowledgement s Afte
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