The expertise in synthetic organic chemistry, especially nitrogen-based heterocycles and carbohydrates, acquired by members of the group “Heterocycles for Societal Challenges” (HSC) have been applied to the design, preparation and characterization of a wide range of novel molecules, mainly tailored to meet the societal needs in terms of new drug candidates or materials.
The group maintains intense collaborative activities reflecting that current research is developed at the interface of organic chemistry with areas such as biology and medicine, physics, materials science and nanotechnology.
- HSC Group Leader: Fernanda Proença
New drug candidates:
The search for new drug candidates reflects the requirements of a society where life expectancy is increasing, reinforcing the need to find solutions for age-related and chronic diseases. Part of the group members has been involved in the synthesis of a broad range of heterocyclic compounds, sugar derivatives and macrocycles either through metal-catalysed reactions or by new synthetic methods, including asymmetric synthesis. Most of the molecules are selected on the basis of in silico screening or molecular docking studies on the relevant targets. The biological activity of the new compounds is tested through external collaborations, in particular as anticancer (Dep.Biologia, ICVS-3Bs, IBMC) and/or antiangiogenics (IPBragança, IPATIMUP and FMUP), antipsychotics (Fac.Farmácia-USCompostela) and antimicrobials (Univ. Fernando Pessoa – Porto, Fac. Farmácia-UP), including the search for new and improved antiturbercular agents (ICVS-3Bs). Studies on the encapsulation of new fluorescent anticancer compounds in nanoliposomes has been developed for drug delivery in collaboration with CFUM.
The quality of our lives is also profoundly influenced by the development of new technological solutions. The access to new molecules provides the basis for the discovery of new materials with improved/specific properties. Part of the group members is dedicated to the design and preparation of new heterocycles for nonlinear optical, photochromic, catalytic and sensor applications, including the synthesis of heterocyclic pi-conjugated systems for organic light-emitting diodes (OLEDs), optical chemosensors, imaging probes or for dye-sensitized solar cell (DSSCs). The optical and electronic properties of the novel heterocyclic systems are evaluated in solution and in solid matrixes through national and international collaborations. In particular as nonlinear optical (CF-UM, Bordeaux Univ-France), photochromic (CQ-UTAD, Barcelona University- Spain), OLEDs (Curtin University-Australia, Bologna University – Italy, University of Coimbra), chemosensor (Polytechnic University of Valencia-Spain) and DSSCs materials (Faculty of Engineering, University of Porto).Carbon nanotubes (CNT) present extraordinary mechanical, thermal and electrical properties and are powerful candidates for diverse industrial applications, depending on the capacity to promote efficient interactions with different substrates. This relies on the appropriate chemical functionalization of the CNT surface and members of the research group developed expertise in this area and in the use of functionalized CNT as precursors of graphene nanoribbons. The research proceeds namely for the modulation of induced pluripotent stem cells differentiation and for composite or sensor applications.
Recent HSC Publications:
- Teacher's experiences in PBL: implications for practice
Alves, A.C.; Sousa, R.M.; Fernandes, S.; Cardoso, E.; Carvalho, M.A.; Fi
European Journal of Engineering Education, 2016
- Chemical characterization, antioxidant, anti-inflammatory and cytotoxic properties of bee venom collected in Northeast Portugal
Sobral, F.; Sampaio, A.; Falc\~ao, S.; Queiroz, M.J.R.P.; Calhelha, R.C&
Food and Chemical Toxicology, 2016
- Highly efficient heterogeneous catalysts for phenol oxidation: Binuclear pyrrolyl-azine metal complexes encapsulated in NaY zeolite
Ku?niarska-Biernacka, I.; Raposo, M.M.M.; Batista, R.; Parpot, P.; Biernacki, K.&a
Microporous and Mesoporous Materials, 2016
- Biological importance of structurally diversified chromenes
Costa, M.; Dias, T.A.; Brito, A.; Proen?a, F.
European Journal of Medicinal Chemistry, 2016
- Synthesis of New Thieno[3, 2-b]pyridines and Thieno[2, 3-b]pyrazines by Palladium Cross-Coupling
Campos, J.F.; Queiroz, M.J.R.P.; Berteina-Raboin, S.
- Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction
Ara\'ujo, R.F.; Proen?a, M.F.; Silva, C.J.; Castro, T.G.; Melle-Fran
- The first catalytic direct C-H arylation on C2 and C3 of thiophene ring applied to thieno-pyridines, -pyrimidines and -pyrazines
Campos, J.F.; Queiroz, M.-J.R.P.; Berteina-Raboin, S.
- Effect of substitution on the ultrafast deactivation of the excited state of benzo[: B] thiophene-arylamines
Pina, J.; Queiroz, M.-J.R.P.; Seixas De Melo, J.
Photochemical and Photobiological Sciences, 2016
- Wild Roman chamomile extracts and phenolic compounds: Enzymatic assays and molecular modelling studies with VEGFR-2 tyrosine kinase
Guimar\~aes, R.; Calhelha, R.C.; Froufe, H.J.C.; Abreu, R.M.V.; Carvalh
Food and Function, 2016
- Synthesis and evaluation of the chromo-fluorogenic recognition ability of imidazoquinoline derivatives toward ions
Mar\'in-Hern\'andez, C.; Santos-Figueroa, L.E.; El Sayed, S.; Pardo, T.; Raposo, M&p
Dyes and Pigments, 2015
- Acid catalyzed synthesis of 2-(2-aminophenyl)quinazoline-4-amine and reaction with aromatic aldehydes
Marinho, E.; Proen?a, M.F.
RSC Advances, 2016
- Magnetoliposomes based on manganese ferrite nanoparticles as nanocarriers for antitumor drugs
Rodrigues, A.R.O.; Ramos, J.M.F.; Gomes, I.T.; Almeida, B.G.; Ara&
RSC Advances, 2016
- Total facial selectivity of a d-erythrosyl aromatic imine in [4π + 2π] cycloadditions; Synthesis of 2-alkylpolyol 1,2,3,4-tetrahydroquinolines
Ferreira, J.; Duarte, V.C.M.; Noro, J.; Gil Fortes, A.; Alves, M.J.
Organic and Biomolecular Chemistry, 2016
- Magnetoliposomes as carriers for promising antitumor thieno[3,2-b]pyridin-7-arylamines: photophysical and biological studies
Rodrigues, A.R.O.; Almeida, B.G.; Rodrigues, J.M.; Queiroz, M.J.R.P&period
RSC Advances, 2017
- Ionic liquids for the electroreductive radical cyclization of unsaturated bromo derivatives catalyzed by Nickel(II) complexes
Neto, M.J.; Du\~nach, E.; Esperan?a, J.M.S.S.; Esteves, A.P.;
Journal of the Electrochemical Society, 2016
- Role of Carbonaceous Fragments on the Functionalization and Electrochemistry of Carbon Materials
Gusm\~ao, R.; Cunha, E.; Paiva, C.; Geraldo, D.; Proen?a, F.; Bento, F&p
- Interaction of fluorescent quinolin-2-one and coumarin derivatives including dipeptides with lipid bilayers
Abreu, A.S.; Hermenegildo, B.F.C.; Ferreira, P.M.T.; Queiroz, M.J.R&period
RSC Advances, 2016
- Synthesis of π-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions
Castro, M.C.R.; Raposo, M.M.M.
- Synthesis of novel 8-(het)aryl-6H-pyrano[4′,3′:4,5]thieno[3,2-b]pyridines by 6-endo-dig cyclization of Sonogashira products and halolacto
Rodrigues, J.M.; Buisson, P.; Pereira, J.M.; Pinheiro, I.M.; Fern\'andez-Marcelo&comm
- Chemical features of Ganoderma polysaccharides with antioxidant, antitumor and antimicrobial activities
Ferreira, I.C.F.R.; Heleno, S.A.; Reis, F.S.; Stojkovic, D.; Queiroz,
- New 2,4,5-triarylimidazoles based on a phenylalanine core: synthesis, photophysical characterization and evaluation as fluorimetric chemosensors for ion recognition
Esteves, C.I.C.; Raposo, M.M.M.; Costa, S.P.G.
Dyes and Pigments, 2016
- Efficient One-Pot Synthesis of Alkyl 3-[4-(Aryl or Heteroaryl)-1 H -1,2,3-triazol-1-yl]thieno[3,2- b ]pyridine-2-carboxylates by 'Click' Cu(I&rpar
Rodrigues, J.M.; Queiroz, M.-J.R.P.
Synthesis (Germany), 2016
- 2-Aryladenine derivatives as a potent scaffold for A<inf>1</inf>, A<inf>3</inf> and dual A<inf>1</inf>/A<inf>3&
Areias, F.; Correia, C.; Rocha, A.; Brea, J.; Castro, M.; Loza, M.I.&
Bioorganic and Medicinal Chemistry, 2019
- Solid and aqueous magnetoliposomes as nanocarriers for a new potential drug active against breast cancer
Rodrigues, A.R.O.; Mendes, P.M.F.; Silva, P.M.L.; Machado, V.A.&
Colloids and Surfaces B: Biointerfaces, 2017
- Antiangiogenic 1-Aryl-3-[3-(thieno[3,2-b]pyridin-7-ylthio)phenyl]ureas Inhibit MCF-7 and MDA-MB-231 Human Breast Cancer Cell Lines Through PI3K/Akt and MAPK/Erk Pathways
Machado, V.A.; Peixoto, D.; Queiroz, M.J.; Soares, R.
Journal of Cellular Biochemistry, 2016
- Development of multifunctional liposomes containing magnetic/plasmonic MnFe <inf>2</inf> O <inf>4</inf> /Au core/shell nanoparticles
Rodrigues, A.R.O.; Matos, J.O.G.; Nova Dias, A.M.; Almeida, B.G.; Pir
- Fastest non-ionic azo dyes and transfer of their thermal isomerisation kinetics into liquid-crystalline materials
Garcia-Amor\'os, J.; R Castro, M.C.; Coelho, P.; Raposo, M.M.M.; Velasco, D&
Chemical Communications, 2016
- Fast (hetero)aryl-benzothiazolium ethenes photoswitches activated by visible-light at room temperature
Coelho, P.J.; Castro, M.C.R.; Raposo, M.M.M.
Dyes and Pigments, 2015
- Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines
Marinho, E.; Proen?a, M.F.
- Synthesis and characterization of novel thieno[3,2-b]thiophene based metal-free organic dyes with different heteroaromatic donor moieties as sensitizers for dye-sensitized solar cells
Fernandes, S.S.M.; Castro, M.C.R.; Mesquita, I.; Andrade, L.; Mendes, A&perio
Dyes and Pigments, 2017