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Baeyer-Villiger Oxidation of 1,7- & 1,9-dibromopentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dioneAkinola, Adeniyi O. 05 1900 (has links)
Baeyer-Villiger oxidation of 1,9-dibromopentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (1,9-dibromo-PCU-8,11-dione) was performed by using an excess amount of m-chloroperbenzoic acid (3 equivalents) and resulted in the formation of the corresponding monolactone. The reaction would not proceed to the dilactone stage. The structure of the reaction product was established unequivocally via single crystal X-ray diffraction. Baeyer-Villiger oxidation of 1,9-dibromo-PCU-8,11-dione using ceric ammonium nitrate (CAN) was also performed and afforded a mixture of lactones. Only one of these lactones, which also contained an alkene functionality, could be isolated and characterized. 1,7-dibromo-PCU-8,11-dione was also reacted with CAN, yielding the mono-lactone, which has also been characterized.
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Nouvelles applications de la réaction de Passerini dans des réactions de type Friedel-Crafts et Tsuji-Trost. / New applications of Passerini reaction in Friedel-Crafts and Tsuji-Trost reactions.Elmamouni, Elhachemia 02 March 2017 (has links)
L’élaboration de synthèses rapides et efficaces de molécules complexes à partir de substrats de départ simples en utilisant un minimum d’étapes constitue un véritable enjeu de la chimie organique contemporaine. Dans ce contexte, les réactions multicomposant, grâce à leur capacité à créer plusieurs liaisons en une étape, offrent une grande efficacité pour synthétiser des structures d’une grande complexité moléculaire. Par ailleurs, la catalyse organométallique s’est considérablement développée ces dernières années, pour devenir un outil de choix pour la formation de liaisons carbone-carbone. La réaction de Tsuji-Trost est notamment un des plus connues dans ce domaineDans le cadre de cette thèse, la découverte de post-condensations originales à partir d’adduits obtenus par les réactions multicomposant impliquant un isonitrile est l’axe majeur de nos recherches. Ces réactions permettent un accès efficace à un large éventail de composés hétérocycliques.Tout d’abord, nous avons développé une nouvelle voie efficace de synthèse des indolylacétamides via une cascade Passerini/Friedel-Crafts à partir d’adduits de Passerini et d’indoles en présence d’un acide de Lewis. Une version monotope de cette cascade a été ainsi développée.Par ailleurs, nous avons exploité la réactivité des hydrazones N-monosubstitués en tant que bis-nucléophile 1,3 en vue de préparer divers dérivés de 2-pyrazolines via une cascade Tsuji-Trost/Cyclisation pallado-catalysée à partir des adduits de Passerini ou de phosphonates. Dans le but de préparer des 2-pyrazolines énantiosélectivement enrichis, une version énantiosélective de cette cascade a été également réalisée à partir d’adduits de Passerini.Enfin, la mise au point d’une nouvelle cascade Tsuji-Trost/Cyclisation exploitant l’allyle méthyle carbonate a permis l’accès rapide à des motifs hétérocycliques de type oxazolidine-2,4-diones en exploitant le dioxyde de carbone généré in situ. / The development of rapid and efficient syntheses of complex molecules from simple starting substrates using a minimum of steps is a real challenge of contemporary organic chemistry. In this context, multicomponent reactions, thanks to their ability to create several one-step bonds, offer a high efficiency in synthesizing structures of great molecular complexity. Moreover, organometallic catalysis has developed considerably in recent years, becoming a tool of choice for the formation of carbon-carbon bonds. The Tsuji-Trost reaction is specially well known in this field.In this thesis, the discovery of the original post-condensations from the adducts obtained by multicomponent reactions involving isonitrile is the major axis of our research. These reactions allow efficient access to a wide range of heterocyclic compounds.First, we have developed a new efficient pathway for the synthesis of indolylacetamides via the Passerini/Friedel-Crafts cascade from the Passerini adducts and indole in the presence of a Lewis acid. A one-pot version of this cascade has been also developed.Furthermore, we have exploited the reactivity of N-monosubstituted hydrazones as 1,3-bis-nucleophile in order to prepare various 2-pyrazoline derivatives via a pallado-catalyzed Tsuji-Trost/Cyclisation cascade from the Passerini adducts or Phosphonates. In order to prepare enantioselectively enriched 2-pyrazolines, the enantioselective version of this cascade was also realized from the Passerini adduct.Finally, the development of a new Tsuji-Trost/Cyclization cascade from the Passerini adducts and the allyl methyl carbonate provide straight fast and efficient access to oxazolidine-2,4-diones heterocyclic units by exploiting the carbon dioxide generated in situ.
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Citotoxicidade e atividade herbicida de análogos sintéticos de 2-acil-cicloexano-1,3-dionas de espécies de Peperomia / Cytotoxicity and herbicidal activity of 2-acyl-cyclohexane-1,3-diones synthetic analogues from Peperomia speciesCorreia, Mauro Vicentini 23 March 2015 (has links)
As 2-acil-cicloexano-1,3-dionas naturais são de ocorrência bastante restrita, sendo relatadas somente em dois gêneros de plantas (Peperomia, Philodendron e Virola) e em insetos das ordens Lepidoptera e Hymenoptera, tendo sido detectadas atividades citotóxica e cairomonal. Foram sintetizados 77 policetídeos da classe das 2-acil-cicloexano-1,3-dionas (36 inéditos) que foram ensaiados quanto à atividade citotóxica em três linhagens de células leucêmicas (K562, Nalm6 e Raji) e também como inibidores da enzima 4-hidroxifenilpiruvato dioxigenase (HPPD), importante alvo para a atividade herbicida. Por meio da análise de relação entre a estrutura e atividade (REA), foi possível determinar os principais requisitos estruturais para as atividades estudadas. A previsão das atividades citotóxicas e de inibição da enzima HPPD das 2-acil-cicloexano-1,3-dionas sintetizadas, foram baseadas em duas metodologias estatísticas (Regressão linear Múltipla (MLR) e Análise Discriminante utilizando mínimos quadrados parciais (PLS-DA)) que foram utilizadas para a construção de modelos quantitativos e qualitativos de previsão. No modelo de regressão linear múltipla (MLR) obteve-se modelos quantitativos que explicam acima de 80% das variâncias das atividades estudadas, com taxas de acertos superiores a 85% na validação externa. Em relação aos modelos de classificação obtidos através do método PLS-DA, foi possível classificar as substâncias como ativas ou inativas, com taxas de acertos superiores a 80% em todos os modelos criados. As características mais importantes para a atividade de inibição da enzima HPPD foi o tamanho da cadeia lateral e a presença do grupo enólico (4a, 5a, 5d e 5e). Para a atividade citotóxica, na série alifática, a cadeia lateral com 9-11 carbonos (4e, 5a e 6a) apresentou melhores índices de inibição e na série aromática as substâncias com a presença de uma insaturação (8a, 11c e 14a) e grupos retiradores no anel aromático (16a, 17c e 19a) foram ativas. / The natural 2-acyl-cyclohexane-1,3-diones have quite restricted occurrence, being reported from only two plant genera (Peperomia, Philodendron and Virola) and from two insects orders, Lepidoptera and Hymenoptera, in which cytotoxic and kairomonal activities were reported. The 77 polyketides of 2-acyl-cyclohexane-1,3-diones type synthesized (36 novel) were tested for cytotoxic activity against three leukemia cells lines (K562, Nalm6 and Raji), and as inhibitors of 4-hydroxyphenyl pyruvate dioxygenase (HPPD) enzyme, an important target for herbicidal activity. The analysis of structure and activity relationship (SAR) revealed the main structural requirements for the activities studied to predict the cytotoxic activity and inhibition of HPPD enzyme of 2-acyl-cyclohexane-1,3-diones. Two statistical methods (Linear Multiple Regression (MLR) and Discriminant Analysis using partial least squares (PLS-DA)) were used for the construction of quantitative and qualitative prediction models. In the multiple linear regression model (MLR), quantitative models explained more than 80% of the variance of the activity, with hit rates higher than 85% in the external validation. In the classification models obtained from the PLS-DA method, the compounds were divided as active or inactive, with hit rates above 80% in all the models generated. The most important characteristics for the inhibition of the activity of the enzyme HPPD were the size of the side chain and the presence of the enolic group (4a, 5a, 5d e 5e). For the cytotoxic activity in the aliphatic series, the side chain with 9-11 carbons (4e, 5a e 6a) showed higher inhibition indices, while for aromatic series conjugation with a double bond (8a, 11c e 14a) and withdrawing groups in the aromatic ring (16a, 17c e 19a) presented higher activity.
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Citotoxicidade e atividade herbicida de análogos sintéticos de 2-acil-cicloexano-1,3-dionas de espécies de Peperomia / Cytotoxicity and herbicidal activity of 2-acyl-cyclohexane-1,3-diones synthetic analogues from Peperomia speciesMauro Vicentini Correia 23 March 2015 (has links)
As 2-acil-cicloexano-1,3-dionas naturais são de ocorrência bastante restrita, sendo relatadas somente em dois gêneros de plantas (Peperomia, Philodendron e Virola) e em insetos das ordens Lepidoptera e Hymenoptera, tendo sido detectadas atividades citotóxica e cairomonal. Foram sintetizados 77 policetídeos da classe das 2-acil-cicloexano-1,3-dionas (36 inéditos) que foram ensaiados quanto à atividade citotóxica em três linhagens de células leucêmicas (K562, Nalm6 e Raji) e também como inibidores da enzima 4-hidroxifenilpiruvato dioxigenase (HPPD), importante alvo para a atividade herbicida. Por meio da análise de relação entre a estrutura e atividade (REA), foi possível determinar os principais requisitos estruturais para as atividades estudadas. A previsão das atividades citotóxicas e de inibição da enzima HPPD das 2-acil-cicloexano-1,3-dionas sintetizadas, foram baseadas em duas metodologias estatísticas (Regressão linear Múltipla (MLR) e Análise Discriminante utilizando mínimos quadrados parciais (PLS-DA)) que foram utilizadas para a construção de modelos quantitativos e qualitativos de previsão. No modelo de regressão linear múltipla (MLR) obteve-se modelos quantitativos que explicam acima de 80% das variâncias das atividades estudadas, com taxas de acertos superiores a 85% na validação externa. Em relação aos modelos de classificação obtidos através do método PLS-DA, foi possível classificar as substâncias como ativas ou inativas, com taxas de acertos superiores a 80% em todos os modelos criados. As características mais importantes para a atividade de inibição da enzima HPPD foi o tamanho da cadeia lateral e a presença do grupo enólico (4a, 5a, 5d e 5e). Para a atividade citotóxica, na série alifática, a cadeia lateral com 9-11 carbonos (4e, 5a e 6a) apresentou melhores índices de inibição e na série aromática as substâncias com a presença de uma insaturação (8a, 11c e 14a) e grupos retiradores no anel aromático (16a, 17c e 19a) foram ativas. / The natural 2-acyl-cyclohexane-1,3-diones have quite restricted occurrence, being reported from only two plant genera (Peperomia, Philodendron and Virola) and from two insects orders, Lepidoptera and Hymenoptera, in which cytotoxic and kairomonal activities were reported. The 77 polyketides of 2-acyl-cyclohexane-1,3-diones type synthesized (36 novel) were tested for cytotoxic activity against three leukemia cells lines (K562, Nalm6 and Raji), and as inhibitors of 4-hydroxyphenyl pyruvate dioxygenase (HPPD) enzyme, an important target for herbicidal activity. The analysis of structure and activity relationship (SAR) revealed the main structural requirements for the activities studied to predict the cytotoxic activity and inhibition of HPPD enzyme of 2-acyl-cyclohexane-1,3-diones. Two statistical methods (Linear Multiple Regression (MLR) and Discriminant Analysis using partial least squares (PLS-DA)) were used for the construction of quantitative and qualitative prediction models. In the multiple linear regression model (MLR), quantitative models explained more than 80% of the variance of the activity, with hit rates higher than 85% in the external validation. In the classification models obtained from the PLS-DA method, the compounds were divided as active or inactive, with hit rates above 80% in all the models generated. The most important characteristics for the inhibition of the activity of the enzyme HPPD were the size of the side chain and the presence of the enolic group (4a, 5a, 5d e 5e). For the cytotoxic activity in the aliphatic series, the side chain with 9-11 carbons (4e, 5a e 6a) showed higher inhibition indices, while for aromatic series conjugation with a double bond (8a, 11c e 14a) and withdrawing groups in the aromatic ring (16a, 17c e 19a) presented higher activity.
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Investigating quinazoline-2,4-dione and fluoroquinolone scaffolds for antibiotic activity and metabolic stabilityAguirre, Arturo Leonardo 01 August 2019 (has links)
Fluoroquinolones are a class of antibiotics used clinically to treat a wide array of bacterial infections. These therapeutics act by targeting a bacterial enzyme required for cell viability, bacterial type-II topoisomerases. Fluoroquinolones act by forming a ternary complex with bacterial type II topoisomerases and cleaved DNA; religation of DNA is subsequently blocked, therefore leading to bacterial cell death. In ternary complex the keto-acid moiety of the fluoroquinolone is complexed with a divalent magnesium ion, forming a drug-magnesium-water bridge to a serine and an aspartate (or glutamate) residue on helix-4 of the topoisomerase enzyme. A major issue with fluoroquinolones is the rise in bacterial resistance. Resistance arises through substitutions of the serine or aspartate/glutamate residue, therefore preventing formation of the magnesium-water bridge and dramatically diminishing the overall antibiotic activity of the fluoroquinolone.
Quinazoline-2,4-diones are structurally similar to fluoroquinolones; diones also form a ternary complex similar to fluoroquinolones, however, these complexes are less active due to lack of a potent magnesium-water bridge interaction in helix-4. While quinazoline-2,4-diones are therefore less potent antibiotics, their non-reliance on the magnesium water bridge generally affords equipotent activity with wild-type and fluoroquinolone-resistant strains of bacteria.
The first objective of this work was to probe the helix-4 interaction of the bacterial type-II topoisomerase by quinazoline-2,4-dione modification, specifically at the N3 and C4 positions of the quinazoline-2,4-dione scaffold to afford potentially new binding contacts. These modified quinazoline-2,4-diones will provide deeper understanding of the helix-4 interaction and potentially afford potent novel quinazoline-2,4-dione scaffolds, against both wild-type and resistant bacteria, for iterative drug design.
Metabolism is one of the primary sources of detoxification, inactivation, and clearance of drugs from the body and is a critical consideration for all early stage therapeutic development. Clinically used fluoroquinolones, i.e. Moxifloxacin and Ciprofloxacin, historically are metabolically stable, and are not known to be metabolized by Phase I and/or Phase II drug metabolizing enzymes. However, major modifications to the Moxifloxacin and Ciprofloxacin scaffolds, due to the development of next generation antibiotics, may display different metabolic stability profiles. Moreover, metabolism of quinazoline-2,4-diones, developed for fluoroquinolone-resistant bacteria, is not extensively studied and may be subject to different metabolic liabilities that may render the quinazoline-2,4-dione an ineffective potential antibiotic.
The second objective of this work was to determine the in vitro Phase I and Phase II metabolic stabilities of fluoroquinolone and quinazoline-2,4-dione scaffolds to determine any structural features that render the potential therapeutic a metabolic liability.
The results from these two objectives have led to the discovery of a novel bacterial type-II topoisomerase catalytic inhibitor and the acquisition of initial metabolic stability data of fluoroquinolone and quinazoline-2,4-dione scaffolds. These findings further promote research into quinazoline-2,4-diones as bacterial topoisomerase targets, and provide metabolic considerations for both fluoroquinolone and quinazoline-2,4-dione therapeutic development, which is severely underrepresented in the field of quinolone antibiotics.
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A Study of Some 1-alkyl-1,2-dihydro-3-hydroxybenzo[g]quinoxaline-5,10-dionesBrown, Jerry 08 1900 (has links)
The experiment in this thesis involves a study of some 1-alkyl-1,2-dihydro-3-hydroxybenzo[g]quinoxaline-5,10-diones.
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Síntese, caracterização e estudo das propriedades fotoluminescente de complexos de európio com ligantes 2-Acilindan-1,3-Dionatos e HeteroaromáticosResende Filho, João Batista Moura de 21 December 2011 (has links)
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Previous issue date: 2011-12-21 / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES / This work shows the synthesis, characterization, and study of the photoluminescent properties of europium(III) complexes with ligands tris-(2-acilindan-1,3-dionatos) (ACIND = 2-acetylindan-1,3-dione; BIND = 2-benzoylindan-1,3-dione; and PROPIND = 2-propionylindan-1,3-dione) and auxiliary coordinating N heteroaromatic ligands (bipy = 2,2'-bipyridine, and phen = 1,10-phenanthroline). The ligands were obtained by condensation reaction of the diethylphthalate ester with a ketone (yields 12%). The β-diketonates ligands showed a high purity, characterized by the following methods: determination of melting point, mass spectrometry and gas chromatography (GC-MS), absorption spectroscopy in the infrared (IR) and 1H nuclear magnetic resonance and 13C (1H and 13C NMR). The Eu-complexes were characterized by complexometric titration and infrared spectroscopy. Complexometric titration data were consistent with the general formulas [Eu(B)3(H2O)2], [Eu(B)3(H2O)(EtOH)] e [Eu(B)3(L-L)], where B is the 2-acylindan-1,3-diones and L-L is a coordinating N bidentate heteroaromatic ligand. The IR spectra give evidences that coordination of the β-diketonates and heteroaromatics ligands to the Eu3+ ions occur through the oxygen atoms of carbonyl groups and nitrogen atoms, respectively. Analysis of the unfolding transitions of 5D0→7FJ in the emission spectra of the europium complexes, can suggests that the Eu3+ ion is located in a chemical environment of low symmetry. The tris-diketonates complexes with auxiliary heteroaromatic ligands present higher values of quantum efficiency (η) when compared with their respective hydrated complexes. However, these values when compared to similar complexes with other auxiliary ligands (phosphinoxides) have significantly lower values of η, suggesting, in accordance with the other luminescence parameters, that the energy is dissipated by the retrotransfer mechanism from excited states of the Eu3+ ion to the 2-acylindan-1,3-dionates ligands. / O presente trabalho retrata a síntese, caracterização e o estudo das propriedades fotoluminescentes de complexos de európio(III) com ligantes tris-(2-acilindan-1,3-dionatos) (ACIND = 2-acetilindan-1,3-diona; BIND = 2-benzoilindan-1,3-diona; e PROPIND = 2-propionoilindan-1,3-diona) e heteroaromáticos auxiliares N coordenantes (bipy = 2,2‟-bipiridina; e phen = 1,10-fenantrolina). Os ligantes foram obtidos via reação de condensação do éster dietilftalato com uma cetona, obtendo-se rendimentos em torno de 12%. Os ligantes β-dicetonatos apresentaram elevado grau de pureza, sendo caracterizados pelos seguintes métodos: determinação de ponto de fusão, espectrometria de massas e cromatografia gasosa (GC-MS), espectroscopia de absorção na região do infravermelho (IV) e ressonância magnética nuclear de 1H e 13C (RMN 1H e RMN 13C). Os dados de titulação complexométrica foram concordantes com as fórmulas gerais [Eu(B)3(H2O)2], [Eu(B)3(H2O)(EtOH)] e [Eu(B)3(L-L)], onde B é uma das 2-acilindan-1,3-dionas sintetizadas e L-L é um ligante heteroaromático bidentado nitrogenado. Os espectros de IV corroboraram que a coordenação dos ligantes β-dicetonatos e heteroaromáticos aos íons Eu3+ ocorre através dos átomos de oxigênio dos grupos carbonila e dos átomos de nitrogênio, respectivamente. Através da análise dos desdobramentos das transições 5D0→7FJ nos espectros de emissão dos complexos de európio, pode-se inferir que o íon Eu3+ encontra-se em um ambiente químico de baixa simetria. Os complexos tris-dicetonatos com os ligantes auxiliares heteroaromáticos apresentaram maiores valores da eficiência quântica (η) quando comparados com os seus respectivos complexos hidratados. Todavia, esses valores quando comparados com complexos análogos com outros ligantes auxiliares (fosfinóxidos) apresentam valores de η significativamente baixo, sugerindo, em conformidade com os demais parâmetros de intensidade de luminescência, que grande parte da energia é dissipada pelo mecanismo de retrotransferência de energia do estado emissor do íon Eu3+ para os estados singletos e tripletos de energias menores dos ligantes 2-acilindan-1,3-dionatos.
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Síntese e investigação de atividades biológicas de Diidro-Piran-2,4-Dionas / Synthesis and investigation Dihydro-pyron-2,4-dione's biological activitiesSouza, Laura Cristiane de 18 December 2007 (has links)
This work presents synthesis of seven dihydro-pyran-2,4-diones and investigation of some of its biological activities (moluscicidal, antiulcer, antioxidant and anticholinesterasic). These compounds were prepared - in yields that had varied of moderate to good (50 - 85%) - through the aldol condensation of β-ketoester’s diânion with an aldehyde or a ketone, basic hydrolysis, followed of lactonization in acid medium. In the first investigation about its biological activities, dihydro-pyran-2,4-diones had been inactive on Biomphalaria glabrata adult, presenting active only on its egg masses. Studies about antiulcer activity were not satisfactory therefore results obtained for dihydro-pyran-2,4-diones were not significantly different of those observed in the control group. For determination of the antioxidant activity, the spectrophotometric assay with stable radical DPPH was chosen. The results obtained for dihydro-pyran-2,4-diones, in this assay, were similar to the observed ones for the positive control used, BHT, and
show that these compounds constitute in a promising synthetic antioxidants. Results obtained still point with respect to a possible correlation between enol concentration in the equilibrium, and the capacity of reduction of free radical DPPH. It was verified that electron withdrawing groups increase the activity, whereas introduction of electron donators groups cause a reduction of the activity. When assays were extended for other acyclic 1,3-dicarbonilic compounds, was verified that these don’t present antioxidant
activity on free radical DPPH. This fact indicates that conformation also can be decisive for manifestation of the studied activity. The inquiry of the anticholinesterasic activity not yet presented results conclusive, but the preliminary assays showed resulted sufficiently promising, with percentage of inhibition of the enzyme acetylcholinesterase between 50% - 60%. / Fundação de Amparo a Pesquisa do Estado de Alagoas / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior / Este trabalho apresenta a síntese de sete diidro-piran-2,4-dionas e a investigação de algumas de suas atividades biológicas (moluscicida, antiúlcera, antioxidante e anticolinesterásica). Estes compostos foram obtidos, em rendimentos que variaram de moderados a bons (50 – 85%), através da condensação aldólica do diânion de um β-cetoéster com um aldeído ou uma cetona, seguido de hidrólise básica do éster e lactonização em meio ácido. Na primeira investigação sobre suas atividades
biológicas, as diidro-piran-2,4-dionas foram inativas frente ao caramujo adulto da espécie Biomphalaria glabrata, apresentando-se ativo apenas frente à sua desova. Os estudos sobre atividade antiúlcera não foram satisfatórios pois os resultados obtidos para as diidro-piran-2,4-dionas não foram significativamente diferentes daqueles observados no grupo controle. Para a determinação da atividade antioxidante escolheu-se o ensaio espectrofotométrico com o radical estável DPPH. Os resultados
obtidos para as diidro-piran-2,4-dionas, neste ensaio, foram similares aos observados para o controle positivo utilizado, BHT, e mostram que estas se constituem numa promissora classe de antioxidantes sintéticos. Os resultados obtidos apontam ainda para uma possível correlação entre a concentração da forma enólica no equilíbrio, o pKa da hidroxila deste enol e a capacidade de redução do radical livre DPPH. Verificou-se que grupos retiradores de elétrons ligados ao anel aumentam a atividade,
enquanto que a introdução de grupos doadores de elétrons causa uma redução da atividade. Ao estender os ensaios para outros compostos 1,3-dicarbonílicos acíclicos, verificou-se que estes não apresentam atividade antioxidante frente ao radical livre DPPH. Este fato indica que a conformação também pode ser decisiva para a manifestação da atividade estudada. A investigação da atividade anticolinesterásica ainda não apresentou dados conclusivos, mas os ensaios preliminares mostraram
resultados bastante promissores, com porcentagem de inibição da enzima acetilcolinesterase entre 50% - 60%.
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Totalsynthese der Mansouramycine A-E aus Streptomyces sp. und Rhodium-katalysierte 1,2-Additionen an cyclische Enone / Total synthesis of Mansouramycine A-E from streptomyces sp. and rhodium catalized 1,2-additions to cyclic enonesBeerlink, Johannes 14 October 2008 (has links)
No description available.
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