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Synthesis of beta-cyclodextrin derivatives for medicinal applications
Popr, Martin ; Jindřich, Jindřich (advisor) ; Veselý, Jan (referee)
Synthesis of monosubstituted β-cyclodextrin derivatives for medicinal applications Abstract This thesis is focused on preparation of a set of β-cyclodextrin derivatives with potential use as scaffolds for a construction of novel MRI contrast agents. Firstly, the skeleton of native β-CD was selectively persubstituted at possitions 6 and equipped with azide functions. Per-6-azido-β-CD was then monosubstituted on secondary face of the macrocycle. (E)-cinnamylbromide and propargylbromide were chosen as suitable reagents. The monosubstitution reaction afforded two types of regioisomers, substituted at position 2I -O- or 3I -O-. These regioisomers were sucessfully separated via preparative column chromatography after peracetylation of all free hydroxyl groups. 2I -O-, 3I -O-formylmethyl- and 3I -O- karboxymethyl- analogues were prepared by oxidative transformation of cinnamyl group. Finally the usability of the formylmethyl- derivative for covalent binding with suitable substrate via reductive amination was confirmed. Keywords: cyclodextrins, monosubstitution, cinnamyl, propargyl, formylmethyl, carboxymethyl, reductive amination, MRI, contrast agents
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Preparation of asymmetrically substituted diphenylacetylenes usable in molecular electronics
Rejšek, Jan ; Veselý, Jan (referee) ; Jindřich, Jindřich (advisor)
Preparation of asymetrically substituted diphenylacetylenes usable in molecular electronics Abstract This bachelor's work deals with synthesis of assymetrically substituted diphenylacetylenes and their transformation into (η4 -cyclobutadiene)-(η5 - cyclopentadienyl)cobalt complexes, which should be used and researched as molecular rotors. Multistep synthesis concerning conversion of primary arylamines into tertiary by N-permethylation, nucleophilic acyl substitution and Sonogashira coupling was prepared asymmetrically substituted diphenylacetylene with, which consequently underwent cycloaddition [2 + 2] with cyclopentadienyldicarbonylcobalt. Creating (η4 -cyclobutadiene)-(η5 -cyclopentadienyl)cobalt complexe was identified by MS. Keywords: diphenylacetylene, Sonogashira coupling, (η4 -cyclobutadiene)- (η5 -cyclopentadienyl)cobalt complex, cycloaddition [2 + 2], molecular rotor
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Synthesis of selectively disubstituted derivatives of alpha-cyclodextrin for chemosensoric applications
Diviš, Martin ; Kroutil, Jiří (referee) ; Jindřich, Jindřich (advisor)
Tato diplomová práce se zabývá problematikou vhodné selektivní derivatizace - cyklodextrinu pro jeho následné použití jako stacionárního chemosenzoru s fluorescenční skupinou. Byla vyvinuta a vypracována metodika pro přípravu selektivně disubstituovaného -CD. Dále byla vyvinuta metodika pro přípravu knihovny linkerů s fluoroforem a jejich navázání na CD. Také byly připraveny linkery pro připojení CD na pevnou fázi. Byla vyvinuta metodika pro připojení jednotlivých linkerů na CD za pomoci "click" reakcí, jmenovitě 1,3-dipolární cykloadice a reduktivní aminace. Nebyla připravena cílová série látek.
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Synthesis of biaryl oxa- and aza-macrocycles
Koščová, Simona ; Hodačová, Jana (advisor) ; Jindřich, Jindřich (referee) ; Macháček, Vladimír (referee) ; Stibor, Ivan (referee)
The Thesis deals with the synthesis of oxa- and aza-maclocycles, in which the basic structttlal unit comprises of the axially chiraÍ bipherryl or l,1..binaphthyl platform. These ligands can exhibit interesting properties in a field of molecular recognition. Crown ethers and their heteroatom analogues are known as exce|lent receptors Íbr conrplexation oť cations, anions or nentral molccules. Aza-macrocycles of the bíphenyl type 1.4 have becn prepared by reductiorr of amicle's 9-12' Although the prrriÍication of polyamines constitutes generally a difficrrlt problcm, the compouncls 1-4 have been ftrlly characterised: tlie compounds 1-3 as hydrobromicles, ancl the cottrpottncl 4 in the ťorrn oťperchloratg' ,Ithe X-ray crystal stťtlctLtlc analysis of, tetrahydrobromide 2 has revealed interesting infoimation about its stnrcture, Lígancl 2 bincls two brornide attions, one aniotr is helcl abovc the plarre of the macrocyclic cavity ancl the seconcl one bclow it. Amino-lactarns 9-12 r'epresent attractive structnres in the area of cupric salts complexation, Despite the structures of ligancls 9 and 10 are similar to each othu, their complexation behaviour is conrpletely different. The ligand 9 í.orms in one step ner'ttral complex [Cu'9.H.zJ with copper at pH about 7, showirrg thrrs excellent preťequisite for...
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