Repository logo
 
Publication

A single-step multicomponent synthesis of a quinoline derivative and the characterization of its cyclodextrin inclusion complex

2021-08-05Journal article Restricted access
Simple item page
dc.contributor.authorPinto, Luciana Matos Alves
dc.contributor.authorAdeoye, Oluwatomide
dc.contributor.authorThomasi, Sérgio Scherrer
dc.contributor.authorFrancisco, Ana Paula
dc.contributor.authorMarques, Helena Cabral
dc.date.accessioned2023-08-25T10:02:12Z
dc.date.available2023-08-25T10:02:12Z
dc.date.issued2021-08-05
dc.date.updated2023-04-17T11:58:18Z
dc.description.abstractMulticomponent synthesis are convergent reactions in which three or more starting materials react in a single step to form the product. In the discovery and development of new drugs, multicomponent reactions offer several advantages over traditional synthesis: shorter experiment time, less need for laboratory techniques and scalability. Thus, the objective of this work was to perform the multicomponent synthesis of a hexahydroquinoline compound whose pharmacological activity has been described previously. The synthesis product was characterized by spectroscopic techniques such as Fourier transform infrared spectrometry and 1H, 13C and HMQC nuclear magnetic resonance (NMR). The mechanism of the reaction was proposed to include a conjugated Michael addition. Subsequently, inclusion complexes (ICs) at 1:1 and 1:2 stoichiometries were prepared with the appropriate cyclodextrin to increase the aqueous solubility and bioavailability of this molecule. Kneading and lyophilization (LYO) methods were used to prepare the inclusion complexes, which were evaluated by phase solubility and 1H NMR spectroscopy, with LYO at a 1:2 stoichiometry having the best results. The ICs were then characterized by differential scanning calorimetry, near-infrared spectroscopy and in vitro dissolution tests, which verified a slower release of the compound with the potential to improve its biological properties.pt_PT
dc.description.sponsorshipThis work was supported by the Research Institute for Medicines (iMed-ULisboa) through FCT/MCTES (UID/DTP/04138/2019), Central de Análise e Prospecção Química (CAPQ), Fundação de Amparo à Pesquisa de Minas Gerais (FAPEMIG), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), and Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq).pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationPinto LMA, Adeoye O, Thomasi SS, Francisco AP, Cabral-Marques H. A single-step multicomponent synthesis of a quinoline derivative and the characterization of its cyclodextrin inclusion complex. Journal of Molecular Structure [Internet]. 5 de agosto de 2021;1237:130391. Disponível em: https://www.sciencedirect.com/science/article/pii/S002228602100524Xpt_PT
dc.identifier.doi10.1016/j.molstruc.2021.130391pt_PT
dc.identifier.issn0022-2860
dc.identifier.slugcv-prod-3236168
dc.identifier.urihttp://hdl.handle.net/10451/59020
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relationResearch Institute for Medicines
dc.relation.publisherversionhttps://www.sciencedirect.com/science/article/abs/pii/S002228602100524Xpt_PT
dc.subjectCyclodextrinpt_PT
dc.subjectGreen chemistrypt_PT
dc.subjectHexahydroquinolinept_PT
dc.subjectMulticomponent synthesispt_PT
dc.subjectSingle-step reactionpt_PT
dc.titleA single-step multicomponent synthesis of a quinoline derivative and the characterization of its cyclodextrin inclusion complexpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleResearch Institute for Medicines
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FDTP%2F04138%2F2019/PT
oaire.citation.startPage130391pt_PT
oaire.citation.titleJournal of Molecular Structurept_PT
oaire.citation.volume1237pt_PT
oaire.fundingStream6817 - DCRRNI ID
person.familyNameAdeoye
person.familyNameFrancisco
person.familyNameMarques
person.givenNameOluwatomide
person.givenNameAna Paula
person.givenNameHelena
person.identifierM-4178-2013
person.identifier.ciencia-id741E-ABD7-324A
person.identifier.ciencia-idDB1F-B511-D3F2
person.identifier.orcid0000-0003-4033-4438
person.identifier.orcid0000-0001-6602-2075
person.identifier.orcid0000-0002-9255-4697
person.identifier.ridB-4823-2016
person.identifier.ridA-9739-2014
person.identifier.scopus-author-id55965119400
person.identifier.scopus-author-id57237689900
person.identifier.scopus-author-id6603071227
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.cv.cienciaidDB1F-B511-D3F2 | Helena Maria Cabral Marques
rcaap.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublicationc300facf-488d-4b27-8034-71a137a3b06c
relation.isAuthorOfPublication4d9578ac-bddd-48d9-90d8-10c764841c9a
relation.isAuthorOfPublicationb30c4f1a-38da-49ed-bfa7-24e6eb08f072
relation.isAuthorOfPublication.latestForDiscoveryb30c4f1a-38da-49ed-bfa7-24e6eb08f072
relation.isProjectOfPublicationf7ed2a0a-c67e-4c12-ad63-b550724e24bf
relation.isProjectOfPublication.latestForDiscoveryf7ed2a0a-c67e-4c12-ad63-b550724e24bf

Files

Original bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
1-s2.0-S002228602100524X-main.pdf
Size:
1.56 MB
Format:
Adobe Portable Document Format
Download
License bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
1.2 KB
Format:
Item-specific license agreed upon to submission
Description:
Download

Collections

FF - CiênciaVitae - Faculdade de Farmácia