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dc.contributor.authorRibeiro, Felipe Vitório
dc.date.accessioned2023-12-21T18:59:37Z-
dc.date.available2023-12-21T18:59:37Z-
dc.date.issued2020-03-06
dc.identifier.citationRIBEIRO, Felipe Vitório. Planejamento, síntese e avaliação antitumoral de derivados di-idropirimidinonas e imidazopiridinas derivadas de 3-ceto-cumarinas substituídas. 2020. 252 f. Tese (Doutorado em Química) - Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, 2020.por
dc.identifier.urihttps://rima.ufrrj.br/jspui/handle/20.500.14407/10253-
dc.description.abstractCâncer é um termo usado para doenças em que células anormais se dividem sem controle e são capazes de invadir outros tecidos, podendo se espalhar para lugares distantes no corpo através dos sistemas sanguíneos e linfáticos por um processo conhecido como metástase, sendo considerado pela Organização Mundial da Saúde um dos maiores problemas de saúde enfrentados pela humanidade neste século. Dentre as várias classes terapêuticas para o tratamento do câncer se encontram as cumarinas e imidazopiridinas, que são alvos de contínuas investigações de interesse biológico devido às suas propriedades farmacológicas e diferentes mecanismos de ação. Dessa forma, a presente tese propõe o planejamento, a síntese de uma série de análogos di-idropirimidinônicos ao monastrol, a determinação da via mecanística reacional, visto que sua obtenção passa por uma reação tricomponente de Biginelli, e sua avaliação biológica. O planejamento, síntese, caracterização e avaliação antiproliferativa de novas imidazopirinas também é foco deste trabalho. As séries aqui descritas foram planejadas através de hibridação molecular do núcleo di-idropirimidinona ou imidazopirina com a subunidade cumarínica. Ambos os núcleos são comprovadamente ativos sobre linhagens de células tumorais. Portanto este trabalho tem como objetivo estudar o processo de síntese das séries planejadas, seu escopo reacional e avaliar suas propriedades antiproliferativas. As séries foram sintetizadas através de reações clássicas de química orgânica. Todas as séries foram caracterizadas por métodos físicos e químicos de análise. Este é o primeiro relato provando por EM-IE e cálculos teóricos que o núcleo cumarínico e o seu mecanismo reacional multicomponente curiosamente passa através de um intermediário de Knoevenagel, que foi considerado improvável pela literatura. As bibliotecas de novos compostos foram obtidas com rendimentos de baixos a excelentes (23-96%), tendo sua estrutura final confirmada, também, por estudos de difração de raios-X. Dentre as di-idropirimidinonas as que se mostram mais ativas frente a célula tumoral PC-3 foram as que possuem um grupo dietilamino da posição 7 da cumarina (CI50 = 3,28 μM) e as com mais semelhança estrutural com o monastrol (CI50 = 8,89 μM), a maioria das substancias testadas foram mais ativas que o monastrol (CI50 = 22,02 μM). E dentre as imidazopiridinas esse perfil de substituição também é o mais ativo (CI50 = 2,07 μM frente a célula B16-F10), sendo dez vezes mais seletiva para a referida célula em comparação a células saudáveis. Pode-se observar então uma análise de relação estrutura atividade muito interessante e compostos promissores em potência e seletividadepor
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorpor
dc.formatapplication/pdf*
dc.languageporpor
dc.publisherUniversidade Federal Rural do Rio de Janeiropor
dc.rightsAcesso Abertopor
dc.subjectCâncerpor
dc.subjectDHPMpor
dc.subjectMecanismo reacionalpor
dc.subjectNovobiocinpor
dc.subjectReação multicomponentepor
dc.subjectCancereng
dc.subjectcoumarinseng
dc.subjectDHPMeng
dc.subjectreaction mechanismeng
dc.subjectmonastroleng
dc.subjectnovobiocineng
dc.subjectmulticomponent reactioneng
dc.titlePlanejamento, síntese e avaliação antitumoral de derivados di-idropirimidinonas e imidazopiridinas derivadas de 3-ceto-cumarinas substituídaspor
dc.title.alternativePlanning, synthesis and antitumor evaluation of derivatives dihydropyrimidinone and imidazopyridine derived from substituted 3-keto-coumarinseng
dc.typeTesepor
dc.description.abstractOtherCancer is a term used for diseases in which abnormal cells divide without control and are able to invade other tissues, and can spread to distant places in the body through the blood and lymphatic systems through a process known as metastasis, being considered by the World Health Organization. One of the biggest health problems facing humanity in this century. Among the various therapeutic classes for the treatment of cancer are coumarins and imidazopyridines, which are the target of continuous investigations of biological interest due to their pharmaceutical properties and different mechanisms of action. Thus, the present thesis proposes the planning, the synthesis of a series of dihydropyrimidinonic analogues to monastrol, the determination of the mechanistic reaction pathway, since its attainment goes through a Biginelli three-component reaction, and its biological evaluation. The planning, synthesis, characterization and antiproliferative evaluation of new imidazopyrines is also a focus of this work. The series described here were planned through molecular hybridization of the dihydropyrimidinone or imidazopyrine nucleus with the coumarin subunit. Both nuclei are proven to be active on tumor cell lines. Therefore, this work aims to study the synthesis process of the planned series, its reaction scope and to evaluate its antiproliferative properties. The series were synthesized through classic reactions of organic chemistry. All series were characterized by physical and chemical methods of analysis. This is the first report proving by MS-ESI and theoretical calculations that the coumarin nucleus and its multicomponent reaction mechanism curiously passes through a Knoevenagel intermediate, which was considered unlikely in the literature. The libraries of new compounds were obtained with low to excellent yields (23-96%), and their final structure was also confirmed by X-ray diffraction studies. Among the dihydropyrimidinones the ones that are most active against the PC-3 tumor cell were those that have a coumarin position 7 diethylamino (IC50 = 3.28 μM) and those with more structural similarity to monastrol (IC50 = 8, 89 μM), most of the tested substances were more active than monastrol (IC50 = 22.02 μM). And among imidazopyridines, this substitution profile is also the most active (IC50 = 2.07 μM for cell B16-F10), being ten times more selective for that cell compared to healthy cells. You can then see a very interesting structure-to-activity analysis and promising compounds in potency and selectivityeng
dc.contributor.advisor1Kümmerle, Arthur Eugen
dc.contributor.advisor1ID053.978.487-78por
dc.contributor.advisor1Latteshttp://lattes.cnpq.br/5598000938584486por
dc.contributor.referee1Kümmerle, Arthur Eugen
dc.contributor.referee1ID053.978.487-78por
dc.contributor.referee1Latteshttp://lattes.cnpq.br/5598000938584486por
dc.contributor.referee2Castro, Rosane Nora
dc.contributor.referee2IDhttps://orcid.org/0000-0001-8983-3786por
dc.contributor.referee2Latteshttp://lattes.cnpq.br/5479814788308057por
dc.contributor.referee3Lacerda, Renata Barbosa
dc.contributor.referee3Latteshttp://lattes.cnpq.br/2068820144272983por
dc.contributor.referee4Mariz e Miranda, Leandro Soter de
dc.contributor.referee4IDhttps://orcid.org/0000-0003-0634-5846por
dc.contributor.referee4Latteshttp://lattes.cnpq.br/7387849390654555por
dc.contributor.referee5Vieira, Daniel Pais Pires
dc.contributor.referee5Latteshttp://lattes.cnpq.br/8564684974338964por
dc.creator.ID124.035.327-89por
dc.creator.Latteshttp://lattes.cnpq.br/6382382867114353por
dc.publisher.countryBrasilpor
dc.publisher.departmentInstituto de Químicapor
dc.publisher.initialsUFRRJpor
dc.publisher.programPrograma de Pós-Graduação em Químicapor
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