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New synthetic methodologies under flow conditions as tool for API synthesis

2022-05Doctoral thesis Open access
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datacite.subject.fosCiências Médicas::Medicina Básicapt_PT
dc.contributor.advisorAfonso, Carlos Alberto Mateus
dc.contributor.advisorLoureiro, Rui Manuel da Silva
dc.contributor.advisorOliveira, Susana Dias Lucas de
dc.contributor.authorCavaca, Lídia A. S.
dc.date.accessioned2022-10-26T09:23:54Z
dc.date.available2025-06-01T00:31:13Z
dc.date.issued2022-05
dc.date.submitted2021-11
dc.description.abstractThe preparation of medicinally relevant small molecules from biomass is a field of interest due to: 1) structural diversity obtained from biomass modification; 2) being potentially more sustainable and environmentally friendly approach, and; 3) more readily available starting materials most likely lead to lower cost of final product. Biomass furanic platforms, including furfural, have attracted special attention from the scientific community. The transformation of furfural to trans-4,5-diamino-cyclopent-2-enones (DCP) has been extensively studied by several research groups, and different methodologies are now available to obtain these compounds. Being a class of molecules with medicinal interest, taking advantage of cyclopentenone rich scaffold is now an eminent strategy to explore other reactivities and obtain novel bioactive molecules. The transformation of furfural to DCP continues to be a current topic of research, and in this thesis, we studied the scalability of the process by developing a continuous flow methodology for easier scale up/out taking into consideration sustainability metrics. Moreover, the challenging preparation of some DCP derivatives bearing electron-poor anilines led us to develop a high-pressure methodology, which ended up to improve DCP yields. Our interest in producing bioactive scaffolds under sustainable conditions prompted us to explore the reactivity of DCP based on the valorisation of furfural. In this sense, we developed a continuous flow hydrogenation of DCP using H-Cube® Mini Plus apparatus with high selectivity towards unprecedent 2,3-diaminocyclopentanones and α-enaminones, including an ATP sensitive potassium channel agonist. The sustainability of the method was also accessed by green metrics. The α-enaminone core reactivity was further studied through photochemical transformations and Diels-Alder reaction using α-enaminone as diene. A series of photochemical reactions were investigated. The carboxylation of in-house prepared aminals and thioaminals was attempted. Thioaminals were prepared in this thesis. The photodecarbonylation of ketones, including 2,3-diaminocyclopentanones, was studied using environmentally friendly ionic liquids, PEG and deep eutectic systems.pt_PT
dc.description.provenanceSubmitted by Paula Guerreiro (passarinho@reitoria.ulisboa.pt) on 2022-10-17T12:19:02Z No. of bitstreams: 1 scnd740052_td_Lídia_Cavaca.pdf: 19335381 bytes, checksum: 1abf2f104c727567c9c8038b872476c7 (MD5)en
dc.description.provenanceMade available in DSpace on 2022-10-26T09:23:54Z (GMT). No. of bitstreams: 1 scnd740052_td_Lídia_Cavaca.pdf: 19335381 bytes, checksum: 1abf2f104c727567c9c8038b872476c7 (MD5) Previous issue date: 2022-05en
dc.identifier.tid101593686pt_PT
dc.identifier.urihttp://hdl.handle.net/10451/54909
dc.language.isoengpt_PT
dc.relationResearch Institute for Medicines
dc.relationResearch Institute for Medicines
dc.relationNEW SYNTHETIC METHODOLOGIES UNDER FLOW CONDITIONS AS TOOL FOR API SYNTHESIS
dc.subjectSustentabilidadept_PT
dc.subjectBiomassapt_PT
dc.subjectCiclopentenonaspt_PT
dc.subjectα-Enaminonaspt_PT
dc.subjectQuímica de Fluxo Contínuopt_PT
dc.subjectSustainabilitypt_PT
dc.subjectBiomasspt_PT
dc.subjectCyclopentenonespt_PT
dc.subjectα-Enaminonespt_PT
dc.subject, Continuous Flow Chemistrypt_PT
dc.titleNew synthetic methodologies under flow conditions as tool for API synthesispt_PT
dc.typedoctoral thesis
dspace.entity.typePublication
oaire.awardTitleResearch Institute for Medicines
oaire.awardTitleResearch Institute for Medicines
oaire.awardTitleNEW SYNTHETIC METHODOLOGIES UNDER FLOW CONDITIONS AS TOOL FOR API SYNTHESIS
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/9471 - RIDTI/PTDC%2FQUI-QOR%2F32008%2F2017/PT
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%2F143127%2F2019/PT
oaire.fundingStream9471 - RIDTI
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameSantos Cavaca
person.givenNameLídia Alexandra
person.identifierA-7395-2017
person.identifier.ciencia-id9114-58F1-1E5F
person.identifier.orcid0000-0002-3434-9134
person.identifier.scopus-author-id57197788134
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.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
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.contributor.authoremailrepositorio@reitoria.ulisboa.pt
rcaap.rightsopenAccesspt_PT
rcaap.typedoctoralThesispt_PT
relation.isAuthorOfPublicationbd189c2a-642f-4437-b702-a1c07912634c
relation.isAuthorOfPublication.latestForDiscoverybd189c2a-642f-4437-b702-a1c07912634c
relation.isProjectOfPublication2dd5e9b2-71e2-4ad2-ae81-e72e2139a57b
relation.isProjectOfPublicationbb00962c-ed82-4d7a-bc37-61df49767d93
relation.isProjectOfPublicationa21e6964-b01b-421e-9356-1ff6579cdd5c
relation.isProjectOfPublication283c5825-7aca-4269-91ff-c897eb7737c7
relation.isProjectOfPublication.latestForDiscoverybb00962c-ed82-4d7a-bc37-61df49767d93
thesis.degree.nameTese de doutoramento, Farmácia (Química Farmacêutica e Terapêutica), Universidade de Lisboa, Faculdade de Farmácia, 2022pt_PT

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