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The synthesis of nucleoside analogues from nitroimidazole precursorsClayton, Russell January 2001 (has links)
An introduction to nucleoside analogues containing heterocyclic sugar mimics and their synthesis is presented. This includes various ring sizes and different heteroatom combinations. concentrated on work between 1995-2000. The synthesis of novel nucleoside analogues from nitroimidazole precursors has been investigated. The regioisorners I-vinyl-4-nitroimidazole and I-vinyl-S-nitroimidazole have been synthesised from the readily available 4/S-nitroimidazole. Also synthesised from 4/S-nitroimidazoIe IS 3-vinyl-imidazo[ 4' ,S' :S,6]pyrido[2,3- d]pyrimidin-8-one, the pyridine stretched analogue of 3-vinylinosine. 1,3-Dipolar cycloaddition reactions of these three molecules are studied, with stabilised and unstabilised 1,3-dipolar compounds. to produce heterocyclic nucleoside analogues. Structures of these cycloadducts are investigated using nrnr studies to determine the regiochemistry of the reactions. This nrnr evidence is supported my MO calculations. Further studies have established synthetic routes to the pyridine stretched analogues of 2'-deoxyadenosine and 2'-deoxyinosine from deoxyribose and 4/5- nitroimidazole, involving directing the coupling of a chlorosugar to the sodium salt of 4-nitroimidazoIe to yield a maximum of the S-nitroimidazole isomer product
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Síntese de derivados aminoquinolínicos e nucleotídeos não-naturais, potenciais agentes antiparasitários e antibacterianosCarmo, Arturene Maria Lino 24 May 2013 (has links)
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Previous issue date: 2013-05-24 / A tese de doutorado intitulada Síntese de Derivados
Aminoquinolínicos e Nucleotídeos Não-Naturais, Potenciais Agentes
Antiparasitários e Antibacterianos está apresentada em dois capítulos que
descrevem a síntese de substâncias com potencial atividade antiparasitária e
antibacteriana.
Foram obtidos 46 compostos nesse trabalho, 31 compostos do capítulo
1, sendo 15 inéditos, e o restante foi desenvolvido durante a realização do
capítulo 2, sendo 8 inéditos.
O capítulo 1 apresenta a síntese de derivados quinolínicos
funcionalizados usando a reação do tipo “click” para obtenção dos conjugados
aminoquinolina/ácido cólico. Inicialmente é apresentada a obtenção dos
derivados aminoquinolinas, aminoalcinoquinolinas e aminodialcinoquinolinas,
estes dois últimos foram usados na reação do tipo “click” para obtenção dos
derivados triazólicos, alguns também foram utilizados como ligantes na síntese
de complexos de Pt (II). Um estudo da relação estrutura/atividade dos
compostos sintetizados foi realizado, permitindo a verificação da importância
biológica dos compostos.
O segundo capítulo envolveu a síntese de derivados nucleotídicos não-
naturais em que o grupo fosfato é substituído por um triazol e foi realizado no
Instituto de Química Molecular de Reims na Universidade de Reims
Champagne-Ardenne CNRS sob a coordenação da professora Dra. Pascale
Clivio, / The doctoral thesis entitled “Synthesis of Derivatives
Aminoquinolínicos and Non-Natural Nucleotides, Potential Antiparasitic
and Antibacterial Agents” is presented in two chapters that describe the
synthesis of substances with potential antibacterial and antiparasitic activity.
46 compounds were obtained in this work, Chapter 1 31 compounds, including
16 unpublished, and the remainder was developed during the course of Chapter
2, and 8 unpublished.
Chapter 1 presents the synthesis of functionalized quinoline using the
click reaction to obtain the conjugated aminoquinoline/cholic acid. Initially it is
presented to obtain the derivatives aminokynolines, and aminoalkynoquinolines
aminodialkynoquinolines, these two latter were functionalized using reaction
type click to prepare the triazoles, some have also been used as binders in the
synthesis of platinum (II) complexes. A study of the structure/activity of the
synthesized compounds was performed by allowing verification of the biological
importance of the compounds.
The second chapter involved the synthesis of non-natural nucleotide in
which the phosphate group is replaced by a triazole and was conducted at the
Institute of Molecular Chemistry of the University of Reims Champagne-Ardenne
Reims CNRS under the supervision of Professor Dr. Pascale Clivio,
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