Submitted by Renata Lopes (renatasil82@gmail.com) on 2017-05-09T19:59:17Z No. of bitstreams: 1 carolinedesouzapereira.pdf: 4207568 bytes, checksum: 599b9a634283c2a1282db76fab98b5ac (MD5) / Approved for entry into archive by Adriana Oliveira (adriana.oliveira@ufjf.edu.br) on 2017-05-17T14:34:53Z (GMT) No. of bitstreams: 1 carolinedesouzapereira.pdf: 4207568 bytes, checksum: 599b9a634283c2a1282db76fab98b5ac (MD5) / Made available in DSpace on 2017-05-17T14:34:53Z (GMT). No. of bitstreams: 1 carolinedesouzapereira.pdf: 4207568 bytes, checksum: 599b9a634283c2a1282db76fab98b5ac (MD5) Previous issue date: 2016-08-05 / CAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior / O estudo de complexos metálicos para uso na quimioterapia teve um grande impulso no final da década de 60 com a descoberta da cisplatina [(cis-diamindicloridoplatina(II)], que é utilizada para diversos tipos de câncer. No entanto, sua eficácia vem sendo limitada devido surgimento de resistência celular e aos efeitos colaterais, desse modo tem-se buscado por compostos que possam agir eficazmente em um grande número de tumores e apresentar menos efeitos colaterais. Desse modo, há uma busca por análogos e por complexos contendo outros metais, como por exemplo o paládio(II) que apresenta uma química de coordenação muito semelhante a da platina(II). Nesse contexto, esse trabalho descreve a síntese, caracterização, atividade citotóxica, atividade antibacteriana e antiparasitária de complexos de platina(II) e paládio(II) com ligantes derivados da benzilpiperazina e do fenil-oxadiazol. Os complexos foram avaliados quanto à citotoxicidade em duas linhagens de células tumorais e uma saudável, por meio da determinação da viabilidade celular. Também foi avaliada a atividade antibacteriana dos complexos por meio da determinação da concentração inibitória mínima (CIM), onde foi possível observar que a coordenação favoreceu a atividade em determinadas cepas. Tendo conhecimento de que muitos complexos de platina(II) e paládio(II) com diaminas tem apresentado boa atividade citotóxica e que o isômero 1,2,4-oxadiazol está presente em compostos com conhecida ação farmacológica optou-se por sintetizar complexos com ligantes diaminados contendo oxadiazol e outros contendo grupos benzílicos. Os compostos sintetizados foram caracterizados por IV, Raman, RMN de 1H, 13C e 195Pt, e CHN. Apenas os compostos 3, 4 e 8 contendo ligantes derivados do fenil-oxadiazol contendo núcleo metálico platina e substituinte NO2 em meta e CF3 em para e contendo paládio e CF3, respectivamente, foram capazes de inibir em 50% a viabilidade celular nas linhagens tumorais sem apresentar o mesmo efeito na linhagem normal, o que demonstra uma seletividade dos mesmos. Com relação à atividade antibacteriana os complexos que mais se destacaram foram os 3, 4, 7 (contendo NO2 em meta e paládio) e 8, ao passo que os ligantes não apresentaram atividade significativa, o que mostra a importância do íon metálico para a atividade, além disso os complexos ativos são derivados dos ligantes contendo o grupo nitro em meta e o grupo CF3 em para como substituinte no anel aromático, logo, os mesmos também contribuíram para a atividade dos complexos. Finalmente, avaliou-se a atividade antitripanossoma e somente os ligantes B e C (contendo NO2), foram capazes de inibir o parasita. / The study of platinum complexes for use in chemotherapy had a big impulse in the late 60’s with discovery of cisplatin [cis-diamminedichloridoplatinum(II)], it is useful for many types of cancer. However, its efficacy is limited by an emergency of cellular resistance and side effects, thus it has been search effective compounds for many cancers and to have less side effects. Thus, there is great interest in search for analogs and complexes containing other metals, for example palladium(II) that presents the coordination chemistry similar to the platinum(II). In this context this work describes the synthesis, characterization, cytotoxic activity, antibacterial activity and antiparasitic activity of platinum(II) and palladium(II) complexes with ligands derived from benzylpiperazine and phenyl-oxadiazole. The cytotoxicity of compounds was investigated in two tumor cell lines and one normal cell to determine cell viability (IC50). The antibacterial activity of complexes was evaluated for minimum inhibitory concentration (MIC), it was possible to observe the coordination favored the activity in some strains. It is knowing that many platinum(II) and palladium(II) complexes with diamines have shown good cytotoxic activity and the isomer 1,2,4-oxadiazole is present in compounds with known pharmacological action it was decided to synthesize complexes with diamines containing oxadiazole and others benzyl groups. The synthesized compounds were characterized by IV, Raman, RMN 1H, 13C and 195Pt, and CHN. Only compounds 3, 4 and 8 containig ligands derivatives from phenyl-oxadiazole containing platinum and NO2 in meta and CF3 in para and containing palladium and CF3, respectively, were able to inhibit in 50% the cellular viability in tumor cell lines without inhibit healthy cells growth, which shows selectivity. The antibacterial activity results of complexes 3, 4, 7 (containing NO2 in meta and palladium) and 8 deserves attention while the ligands do not present significant responses, which shows the importance of the metal ion, besides the active complexes were derived from ligands containing NO2 in meta position and CF3 in para as a substituent on aromatic ring, therefore they also contributed to the complex activity. Finally, was evaluated the antiparasitic activity, however only ligands B and C, NO2 derivatives, inhibited the parasite.

The thesis has been divided in two chapters: Chapter I describes the preparation of primary-amine monocarbamates from enantiopure trans-cyclohexane-1,2-diamines and their use as chiral organocatalysts in the enantioselective Michael addition reaction of aldehydes and ketones to maleimides, to synthesize enantiomerically enriched substituted succinimides. In the conjugate addition reaction of aldehydes to maleimides in conventional volatile organic solvents, it has been found that these organocatalysts are able to generate both enantiomers of the corresponding succinimide using only one enantiomeric form of the catalyst, just by changing the polarity of the solvent. Theoretical calculations justify the mechanism through which this inversion of enantioinduction occurred. In addition, these organocatalysts were used in the enantioselective Michael addition reaction of aldehydes to maleimides, using Deep Eutectic Solvents (DES) as recyclable and environmentally sustainable reaction medium, yielding the corresponding succinimides with excellent yields and high enantioselectivities (up to 94%). The succinimides can be extracted from the DES, which retains the chiral organocatalyst, allowing to reuse both solvent and catalyst. Moreover, the conjugate addition of ketones to maleimides using conventional solvents, allows obtaining the corresponding succinimides with excellent yields but with moderate enantioselectivities (up to 66%). Chapter II shows the results obtained in the enantioselective Michael addition reaction of aldehydes and ketones to nitroalkenes, using the former trans-cyclohexane-1,2-diamine-derived aminocarbamates as chiral organocatalysts, obtaining enantioenriched γ-nitrocarbonyl compounds. In the conjugate addition of isobutyraldehyde to nitroalkenes, the corresponding γ-nitroaldehydes were obtained with enantioselectivities up to 84%. In addition, the enantioselective conjugate addition reaction of ketones to nitroalkenes allowed to obtain interesting γ-nitroketones with high enantioselectivities (up to 96%). Theoretical calculations justify the mechanism involved during this enantioselective process.

Series of homo- and copolyimides containing controlled degrees of sulfonic acid ion conducting pendant groups have been synthesized from both phthalic (five-) and naphthalic (six-membered) dianhydrides and appropriate wholly aromatic diamines and heterocyclic analogues. The goal is to identify thermally and hydrolytically stable ion conducting polymers (ICP) suitable as proton exchange membranes, PEM, for fuel cells. The candidate ICP's have been synthesized and characterized for molecular weight, chemical composition, film forming properties, thermal transition behavior, boiling water stability, solvent solubility and water absorption and conductivity. Commercially available five-membered ring dianhydrides such as 6FDA, BPDA, and six-membered ring dianhydrides such as naphthalene tetracarboxylic dianhydride (NDA) have been used. High molecular weight five-membered ring polyimides were obtained from an equimolar ratio of diamines and dianhydride using a one-pot ester-acid procedure by initially converting the dianhydride to a diester-diacid derivative, followed by the reaction with sulfonated and unsulfonated aryl diamines. The sulfonated diamine monomer was allowed to oligomerize with the diester-diacid of the dianhydride for 2-3 hours, before unsulfonated diamine was charged into the reaction flask. The levels of sulfonation in the polymer backbones were controlled by varying the mole ratio of sulfonated diamine to unsulfonated diamine. For the six-membered ring polyimides, phenolic solvents, e.g. m-cresol, have been used. In general, 4,4′-diamino-biphenyl-2,2′-disulfonic acid (DPS) has been employed as the source of the sulfonated unit. The chemical compositions of both sulfonated and unsulfonated polyimides were obtained using ¹H-NMR and FT-IR. The sulfonic acid contents in both diamine monomers, as well as the sulfonated polyimides were also analyzed by acid-base potentiometric titration. In all cases, high inherent viscosity values and good film forming ability of the polymers were the key indications of high molecular weight. The viscosity values increased with an increase of sulfonation degree in the polymers. This increase of viscosity in these ionomers can be attributed to the increase of polymer chain aggregation with their increasing ionic character. Polymers were fabricated into membranes via solution casting or spin casting from DMAc or m-cresol in order to study film-forming properties. The solution cast dry films of the sulfonated polyimide membranes gave tough, ductile membranes and demonstrated moderate to high water absorption, which is necessary for PEM fuel cells. However, swollen films, in general, showed poor hydrolytic stability which resulted in brittle membranes. The solution-cast membranes were thermally analyzed to study the effect of the degree of sulfonation on the thermal properties of sulfonated polymers. All the thermograms of the sulfonated polyimide films exhibited a two-step degradation behavior. The first weight loss, observed between 300-400 °C, corresponds to desulfonation in the sulfonated block, and the second weight loss, observed for a temperature around 500 °C or above, corresponds to the polymer backbone degradation. The TGA thermograms indicated that the initial weight losses were steeper for polymers with higher sulfonation degrees. Furthermore, the weight loss temperature of sulfonated polyimides decreased and broadened with increasing sulfonation levels. However, the onset temperature of the first weight loss was independent of the degree of sulfonation. Weight loss data in TGA curves of the sulfonated polymers were used to calculate the degree of sulfonation. Experimental and theoretical values were in good agreement with each other. The sulfonated five-membered polyimide membranes were aged in an air-oven at increasing temperatures (30-220 °C) for 30 min and then titrated with TMAH using non-aqueous potentiometric titration. All the films that were aged up to 220 °C were still completely soluble in DMAc. Moreover, the sulfonic acid groups were unchanged. In addition, several new flexible sulfonated and unsulfonated diamines and bis(naphthalic anhydride) monomers containing phosphineoxide [-P(O)-] or sulfone [-S(O)₂ -] moieties in their structure have been synthesized and characterized with various analytical techniques. The structural design of naphthalic polyimides by incorporating bis(naphthalic anhydrides) was one approach to give a better solubility and processability of their related products. Development of an iterative approach for defining the optimum degree of sulfonation that will produce the highest ionic conductivity while still retaining other important properties such as flexibility, strength, hydrolytic stability has been a goal of this research and will be discussed in the thesis. / Ph. D.

Ce projet scientifique porte sur le développement de nouvelles voies d'accès à des composés azotés hautement fonctionnalisés en s'adaptant aux principes de chimie verte. Tout d'abord, une réaction d'Ugi quatre composants à partir d'alcools a été étudiée. L'utilisation de dérivés de l'iode hypervalent comme oxydant en quantités stoechiométriques ou catalytiques a permis de réaliser un processus one-pot oxydation d'alcools/réaction d'Ugi efficace. Par la suite, une nouvelle réaction de Mannich quatre composants, réalisée en présence d'un acide phosphorique dérivé du BINOL, a permis l'accès à des 1,3-diamines énantiopures. La modification de l'électrophile imine par un composé de type diazène a ensuite mené à des précurseurs d'aminocétones ou d'1,2-diamines énantiopures par un procédé alliant catalyse, synthèse asymétrique et utilisation de composés non toxiques.Enfin, dans la continuité des travaux sur la réactivité des énamides, deux nouvelles réactions multicomposants catalysées au fer ont pu être développées. A partir d'énamides, d'un radical libre et de différents nucléophiles, plusieurs dérivés d'aminoalcools ont pu être synthétisés selon des processus propres et sélectifs.

Biobaserade polymerer är en av möjligheterna för att uppnå mer hållbara plaster och produkter. Polyamider (PA) har mångsidiga tillämpningar alltifrån fibrer i kläder till tillämpningar som bildelar. De mest producerade polyamiderna (PA6 och PA66) står för en årlig fossilbränsleförbrukning på nästan 10 miljoner ton. Skadliga effekter berör inte bara produktionsfasen utan även konsumtionsfasen samt hanteringen av uttjänta produkter. Därför är det ett stort behov av att utveckla biobaserade polyamider som är kemiskt återvinningsbara, för att minska miljöpåverkan från dessa material. I detta arbete syntetiserades furanbaserade polyamider (FPA) genom en polykondensationsreaktion mellan hexametylendiamin (HMDA) och en biobaserad disyra, 2,5-furandikarboxylsyra (FDCA). Dessutom framställdes sampolymerer genom att använda olika förhållanden av C6- och C10-diaminer (HMDA och 1,10-dekandiamin). Strukturen och den kemiska sammansättningen av de syntetiserade polymererna och sampolymererna bekräftades med hjälp av Fourier-transform infraröd spektroskopi och kärnresonansspektroskopi. Den högsta molekylvikten som uppnåddes var 9900 g/mol, främst på grund av begränsningar i reaktoruppställningen (avsaknad av ett vakuumsystem och avsaknad av adekvat blandning). Utöver detta identifierades nedbrytningen av FDCA och förångningen av HMDA som potentiella faktorer som hämmade för högre molekylvikt. Baserat på de termiska analyserna visade sig FPA:erna vara amorfa, med en genomsnittlig glastemperatur på 102°C. Vidare visade de syntetiserade polyamiderna hög termisk stabilitet, med en initial nedbrytningstemperatur (motsvarande 5 % viktförlust) på 340°C. / Biobased polymers is one of the pathways to achieve more sustainable plastics and products. Polyamides (PA) are commodity polymers, having versatile applications from fibers in clothes to car parts. The most produced polyamides (PA6 and PA66) account for yearly fossil-fuel consumption of almost 10 million tonnes. The detrimental effects do not only concern the production phase, but also the consumption and end-of-life aspects. Hence, there is a crucial need to develop bio-based polyamides that are chemically recyclable to reduce the environmental impact of these materials.  In this work, furan-based polyamides (FPAs) were synthesized through a polycondensation reaction between hexamethylenediamine (HMDA) and a biobased diacid, 2,5-furandicarboxylic acid (FDCA). In addition, copolymers were made by using different ratios of C6 and C10 diamines (HMDA and 1,10-decanediamine). The structure and chemical composition of the synthesized polymers and copolymers were confirmed using Fourier-transform infrared spectroscopy, and proton nuclear magnetic resonance. The highest molecular weight attained was 9900 g/mol, mainly due to limitations from the reactor setup (absence of a vacuum system and lack of adequate mixing). Adding to this, the degradation of FDCA and the evaporation of HMDA were identified as potential factors inhibiting the increase in molecular weight. Based on the thermal analyses, the FPAs were found to be amorphous, with an average glass transition temperature of 102°C. Further, the synthesized polyamides showed high thermal stability, having an initial degradation temperature (corresponding to 5% weight loss) of 340°C.

La chimie des nitrones est un outil performant en synthèse organique pour accéder à des composés aminés ou N-hydroxyaminés. Très électrophiles, les nitrones peuvent subir facilement des additions nucléophiles conduisant à des N-hydroxylamines. En particulier, la réaction des N-benzylnitrones α-aminées avec des noyaux indoliques permet d'obtenir des N hydroxylamines indoliques β-aminées avec de bons rendements. Celles-ci sont d'excellents intermédiaires-clefs dans la synthèse d'alcaloïdes indoliques bio-actifs d'origine marine comportant le motif 1-(3'-indolyl)-1,2-diaminoéthane tels que le discodermindole, les nortopsentines, les topsentines ou encore les hamacanthines. Nous avons donc développé des voies de synthèse permettant d'obtenir ces alcaloïdes indoliques à partir de N-hydroxylamines indoliques β-aminées. <br /><br />Cependant, la difficulté de déprotection du groupement protecteur benzyle en présence de fonctionnalités chimiques sensibles à l'hydrogénolyse nous a amené à concevoir une nouvelle famille de nitrones protégées par un carbamate de tert-butyle. Celles-ci, après addition nucléophile de réactifs organométalliques, conduisent à des N (Boc) N hydroxylamines dont le groupement protecteur Boc est aisément éliminé en milieu acide. Cette méthode a permis d'accéder à de nouveaux synthons pouvant être facilement valorisés en synthèse organique. Nous avons appliqué cette méthodologie de synthèse à la préparation du zileuton, un composé inhibiteur de la 5-lipoxygénase, ainsi qu'à la préparation de 1,2-diamines indoliques β-aminées, comportant le motif 1-(3'-indolyl)-1,2-diaminoéthane, intermédiaire-clefs dans la synthèse des alcaloïdes indoliques choisis pour cibles. <br /><br />Nous avons ensuite tenté de préparer des N-sulfinyl nitrones, dont le groupement protecteur électroattracteur chiral pourrait facilement être éliminé en milieu acide et induire de bonnes diastéréosélectivités lors d'additions nucléophiles. <br /><br />Enfin, nous présentons les activités biologiques de plusieurs composés issus de ce travail. Nous avons évalué leur cytotoxicité, l'activité inhibitrice de la protéine kinase CK2, l'activité antibactérienne sur Staphylococcus aureus et enfin l'activité inhibitrice de la pompe d'efflux NorA de Staphylococcus aureus.

Fossils fuels are highly demanded in everyday life domestically or industrially. Fossil fuels are finite resources and they are rapidly depleting, as such alternative renewable feedstocks are sought to replace fossil fuels. Tall oil from paper processing and cashew nut shell liquid from the cashew nut industry are the two major renewable sources we studied, they are both waste byproducts, and have the potential to be converted into value-added materials. Tall oil from the paper industry mainly contained tall oil fatty acid, and under isomerising methoxycarbonylation with palladium catalyst, dimethyl 1,19-dimethyl nonadecanedioate can be obtained. This difunctional ester, dimethyl 1,19-dimethyl nonadecanedioate, is converted to diols, secondary and primary diamines by a hydrogenation reaction with ruthenium complexes of 1,1,1-tris(diphenylphosphinometyl)ethane (triphos) as catalysts in the presence of water, amine or aqueous ammonia respectively. In the case of aqueous ammonia it is necessary to use a two step reaction via diol to obtain 1,19-diaminononadecane. Diesters, diols and diamines are useful precursors for the synthesis of polyesters and polyamides. Difunctional substrates with 8-19 carbon chains are all tolerated under the reaction conditions and are successfully converted to the corresponding diols and diamines in high yields. Under similar hydrogenation conditions with the same ruthenium catalyst, cyclic products were predominantly produced with decreased chain length. N-heterocycles, which are important building blocks for the synthesis of drug molecules, were formed from the hydrogenation of diesters with 4-7 carbon chains in the presence of an amine. Another polymer precursor, ε-caprolactam, which is the precursor for Nylon 6, is obtained in a reasonable yield from both adipic acid and adipate esters together with aqueous ammonia in the presence of ruthenium catalyst. Cashew nut shell liquid was also converted into useful medical drugs, such as norfenefrine, rac-phenylephrine, etilefrine and fenoprofene in reasonable yields. Most of these drug molecules have been formed from 3-vinylphenol by catalytic hydroxyamination followed by methylation or ethylation. 3-Vinylphenol was synthesised from cardanol by ethenolysis to 3-non-8-enylphenol followed by isomerising ethenolysis, whilst the N-alkylation reactions used methyl or ethyl triflate to avoid dialkylation. Fenoprofene was formed by firstly O-phenylating cardanol then ethenolysis followed by isomerising ethenolysis to form 1-phenoxy-3-vinylbenzene. Methoxycarbonyation followed by hydrolysis formed the final product in good yield. Our methods start from renewable waste materials and avoid unpleasant reagents in the original stoichiometric synthesis of those drugs, for example, cyanide is no longer essential for the synthesis of fenoprofene.

Transition metal catalysis is a powerful tool for the construction of biologically active and pharmaceutically relevant architectures. With the challenge of continually depleting resources that this generation of scientists faces, it is becoming increasingly important to develop sustainable technologies for organic synthesis that utilize abundant and renewable feedstocks while minimizing byproduct formation and shortening the length of synthetic sequences by removing unnecessary protecting group manipulations and functionalizations. To this end, we have developed four new methods that transform inexpensive starting materials to valuable products. This dissertation covers the following key areas: 1) activation of CO2 for a mild and functional group tolerant synthesis of carboxylic acids, 2) oxidative twofold C–H bond activations as a strategy toward biaryls, 3) migratory O- to N-rearrangements in pyridines and related heterocycles for the preparation of N-alkylated heterocycles, and 4) asymmetric hydrogenations of cyclic imines and enamines en route to chiral 1,2- and 1,3-diamines and macrocyclic peptides.

Transition metal catalysis is a powerful tool for the construction of biologically active and pharmaceutically relevant architectures. With the challenge of continually depleting resources that this generation of scientists faces, it is becoming increasingly important to develop sustainable technologies for organic synthesis that utilize abundant and renewable feedstocks while minimizing byproduct formation and shortening the length of synthetic sequences by removing unnecessary protecting group manipulations and functionalizations. To this end, we have developed four new methods that transform inexpensive starting materials to valuable products. This dissertation covers the following key areas: 1) activation of CO2 for a mild and functional group tolerant synthesis of carboxylic acids, 2) oxidative twofold C–H bond activations as a strategy toward biaryls, 3) migratory O- to N-rearrangements in pyridines and related heterocycles for the preparation of N-alkylated heterocycles, and 4) asymmetric hydrogenations of cyclic imines and enamines en route to chiral 1,2- and 1,3-diamines and macrocyclic peptides.

Submitted by Maike Costa (maiksebas@gmail.com) on 2017-06-06T14:13:28Z No. of bitstreams: 1 arquivototal.pdf: 5719464 bytes, checksum: d95ea796f3e4195aab70df7f60654647 (MD5) / Made available in DSpace on 2017-06-06T14:13:28Z (GMT). No. of bitstreams: 1 arquivototal.pdf: 5719464 bytes, checksum: d95ea796f3e4195aab70df7f60654647 (MD5) Previous issue date: 2017-02-09 / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES / Magadiite (Na2Si14O29.xH2O, x = 5-10) is an alkaline layered silicate with unknown structure and reacts through intercalation with simple organic species and polymer resulting inorganic-organic hybrids, which can be applied as adsorbents for pollutants, catalytic support, cationic exchanger and others. In this work, sodium magadiite was obtained by hydrothermal synthesis and used as support to ion exchange to origin the acid, potassium, calcium and magnesium forms. The acid magadiite interacted with aliphatic diaminas, NH2(CH2)nNH2 where n = 8, 9, 10 e 12, in ethanolic medium, by using conventional and microwave heatings. The exchanged solids were evaluated for the ability to remove ranitidine in aqueous medium where contact time and initial drug concentration parameters were investigated. In vitro release tests were performed for sodium magadiite/ranitidine hybrid. The solids were characterized by X-Ray diffratometry (XRD), infrared spectroscopy (FIRT), CHN elemental analysis, thermogravimetry (TG/DTG) and UV-Vis molecular absorption spectroscopy in solid state before and after interaction with the diamines and drug. Hybrid materials formed between H-magadiite and diamines showed basal spacings between 0.200 to 0.286 nm resulting from the intercalation of both diamines and solvent molecules in the layered material, where the intercalated amount depended of size of organic chain, nature of solvent, temperature and type of heating. The Na-, H-, K-, Ca- and Mg exchanged magadiites removed ranitidine from aqueous solution, and the maximum capacities were 92.34 and 81.47 mg g-1 for sodium and potassium, respectively. The released tests of ranitidine was pH-dependent and presented the maximum released quantities of 76.4% in 48 h at SGF and 43.3% and 46.4% in 56 h in both SIF and SBF. Na- and K-magadiites showed potential adsorbents and drug vehicle for ranitidine while the H-magadiite/diamines intercalated hybrids had new organophilic properties, which result in new properties to interact with new organic species in solution. / A magadeíta (Na2Si14O29.xH2O, x = 5-10) é um silicato lamelar alcalino de estrutura ainda desconhecida que interage por intercalação com espécies orgânicas simples ou polímeros, originando híbridos inorgânico-orgânicos destinados a mais diversas aplicações como adsorventes, suporte para catalisadores, trocador catiônico, entre outras. Neste trabalho, a magadeíta sódica foi obtida por síntese hidrotérmica convencional e por troca iônica originou as suas formas ácida, potássica, cálcica e magnésica. A magadeíta ácida interagiu com diaminas alifáticas, NH2(CH2)nNH2 com n = 8, 9, 10 e 12, em meio etanólico, utilizando aquecimento convencional e por micro-ondas. Os sólidos trocados foram avaliados quanto à capacidade de remoção de ranitidina em meio aquoso, onde os parâmetros de tempo de contato e concentração inicial do fármaco foram investigados. Os ensaios de liberação in vitro foram realizados para o sistema magadeíta sódica/ranitidina. Os sólidos foram caracterizados por difratometria de raios X (DRX), espectroscopia na região do infravermelho (IV), análise elementar de CHN, termogravimetria (TG/DTG) e espectroscopia de absorção molecular UV-Vis no estado sólido antes e após a interação com as diaminas e com o fármaco. Os materiais híbridos formados entre a H-magadeíta e as diaminas mostraram variações no espaçamento basal de 0,200 a 0,286 nm, resultantes da intercalação tanto das diaminas como das moléculas do solvente na matriz lamelar, onde a quantidade intercalada foi dependente do tamanho da cadeia orgânica, temperatura e fonte de aquecimento. A magadeíta em suas formas trocadas com Na-, H-, K-, Ca- e Mg adsorveram ranitidina em meio aquoso cujas capacidades máximas de sorção foram de 92,34 e 81,47 mg g-1 para as formas sódica e potássica, respectivamente. A interação da ranitidina com os sólidos por intercalação também foi confirmada por DRX, IV, CHN e UV-Vis do estado sólido. Os ensaios emissão da ranitidina mostraram que a quantidade liberada foi dependente do pH dos fluidos, apresentando máximos de liberação de 76,4% em 48 h no fluido SGF e de 43,3% e 46,4% em 56 h nos fluidos SIF e SBF, respectivamente. As Na- e K-magadeítas mostraram bons adsorventes e veículo para ranitidina, enquanto os híbridos de intercalação magadeíta ácida/diaminas tiveram novas propriedades organofílicas, o que permite aplicações futuras para interação com diferentes espécies orgânicas em solução.