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Synthesis of bioactive complex structures via valorisation of bio renewable resources

2023-11Tese de doutoramento Acesso embargado
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datacite.subject.fosCiências Médicas::Medicina Básicapt_PT
dc.contributor.advisorAfonso, Carlos A. M.
dc.contributor.advisorGomes, Rafael F. A.
dc.contributor.authorG. Pereira, Juliana
dc.date.accessioned2024-03-19T17:58:56Z
dc.date.embargo2026-12
dc.date.issued2023-11
dc.date.submitted2023-07
dc.description.abstractFuran-based compounds, such as furfural and 5-hydroxymethylfurfural, obtained through the dehydration of pentoses and hexoses from lignocellulosic biomass, are important building blocks in the production of various chemicals. The reactivity of these furanic platforms has been explored to create new chemical entities with high complexity and diversity. This thesis addresses the synthesis of trans-4,5-diamino-cyclopent-2-enones (DCP) from furfural, with a focus on developing an asymmetric methodology in order to produce chiral bifunctionalized cyclopentenones. The formation of chiral centers in these molecules allows for higher molecular complexity and access to a wider chemical space. The potential application of regioselective δ-lactone-fused cyclopentenones (LCP) and trans-4,5-diaminocyclopent-2-enones (DCP) as antimalarial compounds was also studied. Promising IC50 values were obtained for various DCP derivatives, highlighting their potential despite the promiscuity commonly associated with the Michael acceptor of the cyclopentenone core. The synthesis of nitrogen-containing compounds plays a crucial role in the pharmaceutical industry. Sustainable methodologies for the synthesis of 3-acetamido-5-acetylfuran (3A5AF), a promising bio-renewable building block, from chitin (a nitrogen-rich biopolymer), were developed, aiming to overcome limitations of previously reported methods. To optimize the synthetic process, a machine learning-assisted approach was employed, resulting in improved yields. The direct use of 3A5AF as a diene in Diels-Alder (DA) cycloaddition reactions was investigated, leading to the synthesis of 7- oxanorbornenes. The incorporation of renewable nitrogen into these compounds was highlighted to produce polymer materials, fine chemicals, and commodity aromatics. Furthermore, this work explored the formation of aminals from aromatic aldehydes including furfural and HMF under mild conditions. These aminals found utility as aldehyde protection groups, scavengers of potential genotoxic impurities, and stimuli-responsive release systems. Overall, this thesis provides valuable insights into the sustainable synthesis of diverse and complex chemical compounds from biomass-derived furanic platforms, offering new possibilities for the utilization of renewable resources in chemical synthesis and pharmaceutical applications.pt_PT
dc.description.provenanceSubmitted by Paula Guerreiro (passarinho@reitoria.ulisboa.pt) on 2024-02-09T12:23:10Z No. of bitstreams: 1 scnd00001_td_Juliana_Pereira.pdf: 23587157 bytes, checksum: f39e33fdb8e7e974b24e75645ac5b744 (MD5)en
dc.description.provenanceMade available in DSpace on 2024-03-19T17:58:56Z (GMT). No. of bitstreams: 1 scnd00001_td_Juliana_Pereira.pdf: 23587157 bytes, checksum: f39e33fdb8e7e974b24e75645ac5b744 (MD5) Previous issue date: 2023-11en
dc.description.sponsorshipPrograma de investigação e inovação Horizonte 2020 da União Europeiapt_PT
dc.identifier.tid101638183pt_PT
dc.identifier.urihttp://hdl.handle.net/10451/63581
dc.language.isoengpt_PT
dc.relationResearch Institute for Medicines
dc.relationResearch Institute for Medicines
dc.relationSynthesis of bioactive complex structures via valorization of bio renewable resources
dc.subjectSustentabilidadept_PT
dc.subjectBiomassapt_PT
dc.subjectFuranospt_PT
dc.subjectCiclopentenonaspt_PT
dc.subjectAminaispt_PT
dc.subjectSustainabilitypt_PT
dc.subjectBiomasspt_PT
dc.subjectFurfuralspt_PT
dc.subjectCyclopentenonespt_PT
dc.subjectAminalspt_PT
dc.titleSynthesis of bioactive complex structures via valorisation of bio renewable resourcespt_PT
dc.typedoctoral thesis
dspace.entity.typePublication
oaire.awardNumberUIDB/04138/2020
oaire.awardNumberUIDP/04138/2020
oaire.awardNumberPD/BD/143162/2019
oaire.awardTitleResearch Institute for Medicines
oaire.awardTitleResearch Institute for Medicines
oaire.awardTitleSynthesis of bioactive complex structures via valorization of bio renewable resources
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04138%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04138%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//PD%2FBD%2F143162%2F2019/PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameGomes Pereira
person.givenNameJuliana
person.identifier.ciencia-idD117-6BFA-31F3
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.contributor.authoremailrepositorio@reitoria.ulisboa.pt
rcaap.rightsembargoedAccesspt_PT
rcaap.typedoctoralThesispt_PT
relation.isAuthorOfPublication846a9da2-262f-44c4-b101-c5672635eca9
relation.isAuthorOfPublication.latestForDiscovery846a9da2-262f-44c4-b101-c5672635eca9
relation.isProjectOfPublicationbb00962c-ed82-4d7a-bc37-61df49767d93
relation.isProjectOfPublicationa21e6964-b01b-421e-9356-1ff6579cdd5c
relation.isProjectOfPublication4d1a8947-9d9d-42e4-8215-017623646365
relation.isProjectOfPublication.latestForDiscoverya21e6964-b01b-421e-9356-1ff6579cdd5c
thesis.degree.nameTese de doutoramento, Farmácia (Química Farmacêutica e Terapêutica), Universidade de Lisboa, Faculdade de Farmácia, 2023pt_PT

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