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Prof. Marta Pineiro
Department of Chemistry, Universidade de Coimbra, 3004-535, Coimbra, Portugal

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Research Keywords & Expertise

0 Green Chemistry
0 Microwave
0 Mechanochemistry
0 Sustainable synthesis of heterocycles
0 New tools for sustainable synthesis

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Microwave
Green Chemistry
Mechanochemistry
Sustainable synthesis of heterocycles

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Rapid communication
Published: 23 July 2021 in ACS Medicinal Chemistry Letters
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Molecular hybridization is a valuable approach in drug discovery. Combining it with multicomponent reactions is highly desirable, since structurally diverse libraries can be attained efficiently in an eco-friendly manner. In this work, isatin is used as the key building block for the Ugi 4-center 3-component reaction synthesis of oxindole–lactam hybrids, under catalyst-free conditions. The resulting oxindole−β-lactam and oxindole−γ-lactam hybrids were evaluated for their potential to inhibit relevant central nervous system targets, namely cholinesterases and monoamine oxidases. Druglikeness evaluation was also performed, and compounds 4eca and 5dab exhibited great potential as selective butyrylcholinesterase inhibitors, at the low micromolar range, with an interesting predictive pharmacokinetic profile. Our findings herein reported suggest oxindole–lactam hybrids as new potential agents for the treatment of Alzheimer’s disease.

ACS Style

Pedro Brandão; Óscar López; Luisa Leitzbach; Holger Stark; José G. Fernández-Bolaños; Anthony J. Burke; Marta Pineiro. Ugi Reaction Synthesis of Oxindole–Lactam Hybrids as Selective Butyrylcholinesterase Inhibitors. ACS Medicinal Chemistry Letters 2021, 1 .

AMA Style

Pedro Brandão, Óscar López, Luisa Leitzbach, Holger Stark, José G. Fernández-Bolaños, Anthony J. Burke, Marta Pineiro. Ugi Reaction Synthesis of Oxindole–Lactam Hybrids as Selective Butyrylcholinesterase Inhibitors. ACS Medicinal Chemistry Letters. 2021; ():1.

Chicago/Turabian Style

Pedro Brandão; Óscar López; Luisa Leitzbach; Holger Stark; José G. Fernández-Bolaños; Anthony J. Burke; Marta Pineiro. 2021. "Ugi Reaction Synthesis of Oxindole–Lactam Hybrids as Selective Butyrylcholinesterase Inhibitors." ACS Medicinal Chemistry Letters , no. : 1.

Research article
Published: 23 July 2021 in Journal of Chemical Education
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A one-pot regio- and stereoselective synthesis of a dipyrromethane and a bis(indolyl)methane based on two consecutive reactions of nitrosoalkenes with pyrrole or indole, respectively, is described as an experiment to be carried out by upper-division undergraduate students in a laboratory classroom. Importantly, the ability of electrophilic conjugated nitrosoalkenes to react via Michael addition or hetero-Diels–Alder reactions with electron-rich heterocycles will provide an opportunity for students to acknowledge alternative reaction pathways underlying certain transformations. Reactions were performed under mild conditions using water as a solvent, followed by purification through column chromatography on silica gel, and characterization of the desired products by NMR and IR spectroscopy. This laboratory experiment combines organic synthesis, determination of the purity of compounds (TLC analysis and melting point measurements), as well as structural analysis (interpretation of 1D NMR spectra). Several important organic chemistry concepts, such as stereo- and regioselectivity, in situ generation and reactivity of conjugated nitrosoalkenes, conjugated 1,4-addition reactions, and cycloaddition reactions, are also discussed.

ACS Style

Ana L. Cardoso; Susana M. M. Lopes; Carla Grosso; Marta Pineiro; Américo Lemos; Teresa M. V. D. Pinho e Melo. One-Pot Synthetic Approach to Dipyrromethanes and Bis(indolyl)methanes via Nitrosoalkene Chemistry. Journal of Chemical Education 2021, 98, 2661 -2666.

AMA Style

Ana L. Cardoso, Susana M. M. Lopes, Carla Grosso, Marta Pineiro, Américo Lemos, Teresa M. V. D. Pinho e Melo. One-Pot Synthetic Approach to Dipyrromethanes and Bis(indolyl)methanes via Nitrosoalkene Chemistry. Journal of Chemical Education. 2021; 98 (8):2661-2666.

Chicago/Turabian Style

Ana L. Cardoso; Susana M. M. Lopes; Carla Grosso; Marta Pineiro; Américo Lemos; Teresa M. V. D. Pinho e Melo. 2021. "One-Pot Synthetic Approach to Dipyrromethanes and Bis(indolyl)methanes via Nitrosoalkene Chemistry." Journal of Chemical Education 98, no. 8: 2661-2666.

Journal article
Published: 11 June 2021 in Communications Chemistry
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Aqueous organic redox flow batteries (AORFBs) hold great promise as low-cost, environmentally friendly and safe alternative energy storage media. Here we present aqueous organometallic and all-organic active materials for RFBs with a water-soluble active material, sulfonated tryptanthrin (TRYP-SO3H), working at a neutral pH and showing long-term stability. Electrochemical measurements show that TRYP-SO3H displays reversible peaks at neutral pH values, allowing its use as an anolyte combined with potassium ferrocyanide or 4,5-dihydroxy-1,3-benzenedisulfonic acid disodium salt monohydrate as catholytes. Single cell tests show reproducible charge-discharge cycles for both catholytes, with significantly improved results for the aqueous all-organic RFB reaching high cell voltage (0.94 V) and high energy efficiencies, stabilized during at least 50 working cycles.

ACS Style

Daniela Pinheiro; Marta Pineiro; J. Sérgio Seixas de Melo. Sulfonated tryptanthrin anolyte increases performance in pH neutral aqueous redox flow batteries. Communications Chemistry 2021, 4, 1 -10.

AMA Style

Daniela Pinheiro, Marta Pineiro, J. Sérgio Seixas de Melo. Sulfonated tryptanthrin anolyte increases performance in pH neutral aqueous redox flow batteries. Communications Chemistry. 2021; 4 (1):1-10.

Chicago/Turabian Style

Daniela Pinheiro; Marta Pineiro; J. Sérgio Seixas de Melo. 2021. "Sulfonated tryptanthrin anolyte increases performance in pH neutral aqueous redox flow batteries." Communications Chemistry 4, no. 1: 1-10.

Research article
Published: 14 April 2021 in The Journal of Physical Chemistry B
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In indigo, excited state proton transfer (ESPT) is known to be associated with the molecular mechanism responsible for highly efficient radiationless deactivation. When this route is blocked (partially or totally), new deactivation routes become available. Using new green chemistry procedures, with favorable green chemistry metrics, monosubstitution and disubstitution of N group(s) in indigo, by tert-butoxy carbonyl groups, N-(tert-butoxycarbonyl)indigo (NtBOCInd) and N,N′-(tert-butoxycarbonyl)indigo (N,N’tBOCInd), respectively, were synthetically accomplished. The compounds display red to purple colors depending on the solvent and substitution. Different excited-state deactivation pathways were observed and found to be structure- and solvent-dependent. Trans–cis photoisomerization was found to be absent with NtBOCInd and present with N,N’tBOCInd in nonpolar solvents. Time-resolved fluorescence experiments revealed single-exponential decays for the two compounds which, linked to time-dependent density functional theory (TDDFT) studies, show that with NtBOCInd ESPT is extremely fast and barrierless—predicted to be 1 kJ mol–1 in methylcyclohexane and 5 kJ mol–1 in dimethylsulfoxide—, which contrasts with ∼11 kJ mol–1 experimentally obtained for indigo. An alternative ESPT, competitive with the N–H···O═C intramolecular pathway, involving dimer units is also probed by TDDFT and found to be consistent with the experimentally observed time-resolved data. N,N’tBOCInd, where ESPT is precluded, shows solvent-dependent trans–cis/cis–trans photoisomerization and is surprisingly found to be more stable in the nonemissive cis conformation, whose deactivation to S0 is found to be solvent-dependent.

ACS Style

Daniela Pinheiro; Adelino M. Galvão; Marta Pineiro; J. Sérgio Seixas de Melo. Red-Purple Photochromic Indigos from Green Chemistry: Mono-tBOC or Di-tBOC N-Substituted Indigos Displaying Excited State Proton Transfer or Photoisomerization. The Journal of Physical Chemistry B 2021, 125, 4108 -4119.

AMA Style

Daniela Pinheiro, Adelino M. Galvão, Marta Pineiro, J. Sérgio Seixas de Melo. Red-Purple Photochromic Indigos from Green Chemistry: Mono-tBOC or Di-tBOC N-Substituted Indigos Displaying Excited State Proton Transfer or Photoisomerization. The Journal of Physical Chemistry B. 2021; 125 (16):4108-4119.

Chicago/Turabian Style

Daniela Pinheiro; Adelino M. Galvão; Marta Pineiro; J. Sérgio Seixas de Melo. 2021. "Red-Purple Photochromic Indigos from Green Chemistry: Mono-tBOC or Di-tBOC N-Substituted Indigos Displaying Excited State Proton Transfer or Photoisomerization." The Journal of Physical Chemistry B 125, no. 16: 4108-4119.

Research article
Published: 14 April 2021 in RSC Medicinal Chemistry
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Novel 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused chlorins, derived from 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin, as impressive photosensitizers for photodynamic therapy of melanoma and esophagus cancer have been developed.

ACS Style

Nelson A. M. Pereira; Mafalda Laranjo; Bruno F. O. Nascimento; João C. S. Simões; João Pina; Bruna D. P. Costa; Gonçalo Brites; João Braz; J. Sérgio Seixas de Melo; Marta Pineiro; Maria Filomena Botelho; Teresa M. V. D. Pinho e Melo. Novel fluorinated ring-fused chlorins as promising PDT agents against melanoma and esophagus cancer. RSC Medicinal Chemistry 2021, 12, 615 -627.

AMA Style

Nelson A. M. Pereira, Mafalda Laranjo, Bruno F. O. Nascimento, João C. S. Simões, João Pina, Bruna D. P. Costa, Gonçalo Brites, João Braz, J. Sérgio Seixas de Melo, Marta Pineiro, Maria Filomena Botelho, Teresa M. V. D. Pinho e Melo. Novel fluorinated ring-fused chlorins as promising PDT agents against melanoma and esophagus cancer. RSC Medicinal Chemistry. 2021; 12 (4):615-627.

Chicago/Turabian Style

Nelson A. M. Pereira; Mafalda Laranjo; Bruno F. O. Nascimento; João C. S. Simões; João Pina; Bruna D. P. Costa; Gonçalo Brites; João Braz; J. Sérgio Seixas de Melo; Marta Pineiro; Maria Filomena Botelho; Teresa M. V. D. Pinho e Melo. 2021. "Novel fluorinated ring-fused chlorins as promising PDT agents against melanoma and esophagus cancer." RSC Medicinal Chemistry 12, no. 4: 615-627.

Research article
Published: 09 April 2021 in The Journal of Physical Chemistry C
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The synthesis, electronic spectral, and photophysical properties of a new bithiophene derivative, (2,2′-bithiophene)-3,5,5′-trisulfonic acid, α2-SO3H, were investigated in organic or aqueous solution, in neat oil form, and in the solid state by cointercalation with different amounts of the surfactant 1-heptanesulfonate (HS) into a layered double hydroxide (LDH). In solution the fluorescence quantum yield (ϕF) of α2-SO3H increases by 1 order of magnitude when compared to the unsubstituted bithiophene (α2) counterpart. However, the most dramatic change is obtained when α2-SO3H is incorporated with HS into a Zn,Al-LDH, where values of ϕF up to 58% are obtained in comparison with values of 4% for neat α2-SO3H (as an oil) and 2% for an LDH containing only α2-SO3H. In the solid state (LDH), in addition to the monomeric form of α2-SO3H, H- and other types of aggregates are present, which are found to be dependent on the percentage HS content. Time-resolved fluorescence studies further rationalize this behavior with single and double exponential decays mirroring the contributions of monomers and aggregates. The study validates a strategy of increasing fluorescence in the solid state by introduction of electrodonating groups and isolation of the α2-SO3H units within the LDH structure with an appropriate surfactant (HS).

ACS Style

Estefanía Delgado-Pinar; Ana L. Costa; Isabel S. Gonçalves; Marta Pineiro; Martyn Pillinger; J. Sérgio Seixas de Melo. Tuning the Behavior of a Hydrotalcite-Supported Sulfonated Bithiophene from Aggregation-Caused Quenching to Efficient Monomer Luminescence. The Journal of Physical Chemistry C 2021, 125, 8294 -8303.

AMA Style

Estefanía Delgado-Pinar, Ana L. Costa, Isabel S. Gonçalves, Marta Pineiro, Martyn Pillinger, J. Sérgio Seixas de Melo. Tuning the Behavior of a Hydrotalcite-Supported Sulfonated Bithiophene from Aggregation-Caused Quenching to Efficient Monomer Luminescence. The Journal of Physical Chemistry C. 2021; 125 (15):8294-8303.

Chicago/Turabian Style

Estefanía Delgado-Pinar; Ana L. Costa; Isabel S. Gonçalves; Marta Pineiro; Martyn Pillinger; J. Sérgio Seixas de Melo. 2021. "Tuning the Behavior of a Hydrotalcite-Supported Sulfonated Bithiophene from Aggregation-Caused Quenching to Efficient Monomer Luminescence." The Journal of Physical Chemistry C 125, no. 15: 8294-8303.

Letter
Published: 03 April 2021 in Green Chemistry Letters and Reviews
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The synthesis of chlorins was performed by hydrogenation of porphyrins using diimide generated and consumed under mechanical activation. The reaction conditions achievable under ball milling, absence of solvent and use of hydrazine hydrate as diimide source, allowed the hydrogenation of porphyrins with high conversion, high selectivity, and nearly ideal sustainability scores (atom economy of 97% and E-factor of 0.96). GRAPHICAL ABSTRACT

ACS Style

Marta Pineiro; Carla Gomes; Mariana Peixoto. Mechanochemical in situ generated gas reactant for the solvent-free hydrogenation of porphyrins. Green Chemistry Letters and Reviews 2021, 14, 339 -344.

AMA Style

Marta Pineiro, Carla Gomes, Mariana Peixoto. Mechanochemical in situ generated gas reactant for the solvent-free hydrogenation of porphyrins. Green Chemistry Letters and Reviews. 2021; 14 (2):339-344.

Chicago/Turabian Style

Marta Pineiro; Carla Gomes; Mariana Peixoto. 2021. "Mechanochemical in situ generated gas reactant for the solvent-free hydrogenation of porphyrins." Green Chemistry Letters and Reviews 14, no. 2: 339-344.

Record review
Published: 18 February 2021 in The Chemical Record
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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

ACS Style

Pedro Brandão; Carolina S. Marques; Elisabete P. Carreiro; M. Pineiro; Anthony J. Burke. Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity. The Chemical Record 2021, 21, 924 -1037.

AMA Style

Pedro Brandão, Carolina S. Marques, Elisabete P. Carreiro, M. Pineiro, Anthony J. Burke. Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity. The Chemical Record. 2021; 21 (4):924-1037.

Chicago/Turabian Style

Pedro Brandão; Carolina S. Marques; Elisabete P. Carreiro; M. Pineiro; Anthony J. Burke. 2021. "Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity." The Chemical Record 21, no. 4: 924-1037.

Review article
Published: 18 December 2020 in European Journal of Medicinal Chemistry
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Oxindole derivatives are known for their great interest in the field of Medicinal Chemistry, as they display vast biological activities. Recent efforts concerning the preparation of oxindole derivatives using isatin-based multicomponent reactions (MCRs) constitute a great advance in generating druglike libraries fast and with wide scaffold diversity. In this review, we address those recent developments, exploring the synthetic pathways and biological activities described for these compounds, namely antitumor, antibacterial, antifungal, antiparasitic, antiviral, antioxidant, anti-inflammatory and central nervous system (CNS) pathologies. To add new depth to this work, we used a well-established web-based free tool (SwissADME) to evaluate the most promising scaffolds in what concerns their druglike properties, namely by evaluating their compliance with some of the most valuable rules applied by medicinal chemists in both academia and industrial settings (Lipinski, Ghose, Veber, Egan, Muegge). The aim of this review is to endorse isatin-based MCRs as a valuable synthetic approach to attain new hit compounds bearing the oxindole privileged structure, while critically exploring these scaffolds’ druglike properties.

ACS Style

Pedro Brandão; Carolina Marques; Anthony J. Burke; Marta Pineiro. The application of isatin-based multicomponent-reactions in the quest for new bioactive and druglike molecules. European Journal of Medicinal Chemistry 2020, 211, 113102 .

AMA Style

Pedro Brandão, Carolina Marques, Anthony J. Burke, Marta Pineiro. The application of isatin-based multicomponent-reactions in the quest for new bioactive and druglike molecules. European Journal of Medicinal Chemistry. 2020; 211 ():113102.

Chicago/Turabian Style

Pedro Brandão; Carolina Marques; Anthony J. Burke; Marta Pineiro. 2020. "The application of isatin-based multicomponent-reactions in the quest for new bioactive and druglike molecules." European Journal of Medicinal Chemistry 211, no. : 113102.

Edge article
Published: 22 October 2020 in Chemical Science
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Using green chemistry procedures the synthesis of N- and N,N′-alkyl indigo derivatives was undertaken and the effect of the alkyl chain length on the spectral (including color) and photophysical properties of the compounds explored.

ACS Style

Daniela Pinheiro; Marta Pineiro; Adelino M. Galvão; J. Sérgio Seixas de Melo. Deep in blue with green chemistry: influence of solvent and chain length on the behaviour of N- and N,N′- alkyl indigo derivatives. Chemical Science 2020, 12, 303 -313.

AMA Style

Daniela Pinheiro, Marta Pineiro, Adelino M. Galvão, J. Sérgio Seixas de Melo. Deep in blue with green chemistry: influence of solvent and chain length on the behaviour of N- and N,N′- alkyl indigo derivatives. Chemical Science. 2020; 12 (1):303-313.

Chicago/Turabian Style

Daniela Pinheiro; Marta Pineiro; Adelino M. Galvão; J. Sérgio Seixas de Melo. 2020. "Deep in blue with green chemistry: influence of solvent and chain length on the behaviour of N- and N,N′- alkyl indigo derivatives." Chemical Science 12, no. 1: 303-313.

Paper
Published: 10 August 2020 in Dalton Transactions
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A water soluble and highly fluorescent bithiophene was obtained. The excited state behavior is fully characterized and with tert-butylsulfonamide derivatization the recognition of Cu(ii) and Hg(ii) with high selectivity was observed.

ACS Style

Estefanía Delgado-Pinar; Marta Pineiro; Joao Sergio Seixas de Melo. A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability. Dalton Transactions 2020, 49, 1 .

AMA Style

Estefanía Delgado-Pinar, Marta Pineiro, Joao Sergio Seixas de Melo. A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability. Dalton Transactions. 2020; 49 (35):1.

Chicago/Turabian Style

Estefanía Delgado-Pinar; Marta Pineiro; Joao Sergio Seixas de Melo. 2020. "A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability." Dalton Transactions 49, no. 35: 1.

Review
Published: 29 July 2020 in Molecules
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Corroles and hexaphyrins are porphyrinoids with great potential for diverse applications. Like porphyrins, many of their applications are based on their unique capability to interact with light, i.e., based on their photophysical properties. Corroles have intense absorptions in the low-energy region of the uv-vis, while hexaphyrins have the capability to absorb light in the near-infrared (NIR) region, presenting photophysical features which are complementary to those of porphyrins. Despite the increasing interest in corroles and hexaphyrins in recent years, the full potential of both classes of compounds, regarding biological applications, has been hampered by their challenging synthesis. Herein, recent developments in the synthesis of corroles and hexaphyrins are reviewed, highlighting their potential application in photodynamic therapy.

ACS Style

Susana M. M. Lopes; Marta Pineiro; Teresa M. V. D. Pinho E Melo. Corroles and Hexaphyrins: Synthesis and Application in Cancer Photodynamic Therapy. Molecules 2020, 25, 3450 .

AMA Style

Susana M. M. Lopes, Marta Pineiro, Teresa M. V. D. Pinho E Melo. Corroles and Hexaphyrins: Synthesis and Application in Cancer Photodynamic Therapy. Molecules. 2020; 25 (15):3450.

Chicago/Turabian Style

Susana M. M. Lopes; Marta Pineiro; Teresa M. V. D. Pinho E Melo. 2020. "Corroles and Hexaphyrins: Synthesis and Application in Cancer Photodynamic Therapy." Molecules 25, no. 15: 3450.

Minireview
Published: 26 May 2020 in European Journal of Organic Chemistry
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In the context of synthetic chemistry, Indium is one of the least explored elements of the notorious group 13 of the periodic table, and hasn´t attracted quite the same amount of attention as its fellow members, Aluminium and Boron, which have shown unprecedented synthetic applications for more than a half a century. Nonetheless, Indium has emerged in recent years as a very valuable catalyst for multicomponent reactions. From the use of indium powder or easily accessible and cheap indium salts, to more complex indium‐based metal organic frameworks or nanoparticles, a plethora of applications have been described throughout this last decade, showcasing not only the versatility of indium catalysis, but also how much there is still to be explored. In the aftermath of the international year of the periodic table of the chemical elements in 2019, we navigated through the large inventory of multicomponent reactions (MCRs) in an effort to encounter the types of useful reactions leading to important target compounds (many of which being biologically active) catalyzed by this d ‐block post‐transition metal.

ACS Style

Pedro Brandão; Anthony J. Burke; Marta Pineiro. A Decade of Indium‐Catalyzed Multicomponent Reactions (MCRs). European Journal of Organic Chemistry 2020, 2020, 5501 -5513.

AMA Style

Pedro Brandão, Anthony J. Burke, Marta Pineiro. A Decade of Indium‐Catalyzed Multicomponent Reactions (MCRs). European Journal of Organic Chemistry. 2020; 2020 (34):5501-5513.

Chicago/Turabian Style

Pedro Brandão; Anthony J. Burke; Marta Pineiro. 2020. "A Decade of Indium‐Catalyzed Multicomponent Reactions (MCRs)." European Journal of Organic Chemistry 2020, no. 34: 5501-5513.

Research article
Published: 08 May 2020 in ACS Omega
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Mechanochemistry is an alternative for sustainable solvent-free processes that has taken the big step to become, in the near future, a useful synthetic method for academia and the fine chemical industry. The apparatus available, based on ball milling systems possessing several optimizable variables, requires too many control and optimization experiments to ensure reproducibility, which has limited its widespread utilization so far. Herein, we describe the development of an automatic mechanochemical single-screw device consisting of an electrical motor, a drill, and a drill chamber. The applicability and versatility of the new device are demonstrated by the implementation of di- and multicomponent chemical reactions with high reproducibility, using mechanical action exclusively. As examples, chalcones, dihydropyrimidinones, dihydropyrimidinethiones, pyrazoline, and porphyrins, were synthesized with high yields. The unprecedented sustainability is demonstrated by comparison of EcoScale and E-factor values of these processes with those previously described in the literature.

ACS Style

Carla Gomes; Carolina S. Vinagreiro; Liliana Damas; Gilberto Aquino; Joana Quaresma; Cristina Chaves; João Pimenta; José Campos; Mariette Pereira; Marta Pineiro. Advanced Mechanochemistry Device for Sustainable Synthetic Processes. ACS Omega 2020, 5, 10868 -10877.

AMA Style

Carla Gomes, Carolina S. Vinagreiro, Liliana Damas, Gilberto Aquino, Joana Quaresma, Cristina Chaves, João Pimenta, José Campos, Mariette Pereira, Marta Pineiro. Advanced Mechanochemistry Device for Sustainable Synthetic Processes. ACS Omega. 2020; 5 (19):10868-10877.

Chicago/Turabian Style

Carla Gomes; Carolina S. Vinagreiro; Liliana Damas; Gilberto Aquino; Joana Quaresma; Cristina Chaves; João Pimenta; José Campos; Mariette Pereira; Marta Pineiro. 2020. "Advanced Mechanochemistry Device for Sustainable Synthetic Processes." ACS Omega 5, no. 19: 10868-10877.

Review
Published: 28 November 2019 in Molecules
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This review presents the most recent developments on the synthesis of dipyrromethanes, covering classical synthetic strategies, using acid catalyzed condensation of pyrroles and aldehydes or ketones, and recent breakthroughs which allow the synthesis of these type of heterocycles with new substitution patterns.

ACS Style

Bruno F. O. Nascimento; Susana M. M. Lopes; Marta Pineiro; Teresa M. V. D. Pinho E Melo. Current Advances in the Synthesis of Valuable Dipyrromethane Scaffolds: Classic and New Methods. Molecules 2019, 24, 4348 .

AMA Style

Bruno F. O. Nascimento, Susana M. M. Lopes, Marta Pineiro, Teresa M. V. D. Pinho E Melo. Current Advances in the Synthesis of Valuable Dipyrromethane Scaffolds: Classic and New Methods. Molecules. 2019; 24 (23):4348.

Chicago/Turabian Style

Bruno F. O. Nascimento; Susana M. M. Lopes; Marta Pineiro; Teresa M. V. D. Pinho E Melo. 2019. "Current Advances in the Synthesis of Valuable Dipyrromethane Scaffolds: Classic and New Methods." Molecules 24, no. 23: 4348.

Cover picture
Published: 14 November 2019 in European Journal of Organic Chemistry
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ACS Style

Pedro Brandão; Marta Pineiro; Teresa M. V. D. Pinho E Melo. Cover Feature: Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis (Eur. J. Org. Chem. 43/2019). European Journal of Organic Chemistry 2019, 2019, 7187 -7187.

AMA Style

Pedro Brandão, Marta Pineiro, Teresa M. V. D. Pinho E Melo. Cover Feature: Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis (Eur. J. Org. Chem. 43/2019). European Journal of Organic Chemistry. 2019; 2019 (43):7187-7187.

Chicago/Turabian Style

Pedro Brandão; Marta Pineiro; Teresa M. V. D. Pinho E Melo. 2019. "Cover Feature: Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis (Eur. J. Org. Chem. 43/2019)." European Journal of Organic Chemistry 2019, no. 43: 7187-7187.

Minireview
Published: 31 October 2019 in European Journal of Organic Chemistry
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Flow Chemistry is a revolutionary field in Organic Chemistry. By changing the conventional methods and apparatus applied in the chemical synthesis, flow chemistry emerges as a game changer for organic synthesis laboratories, in both academia and industries. Considered as a sustainable practice, flow processes play an important role in the development of fine chemical products and in drug discovery development programs. This work aims to review the recent contributions on heterocyclic synthesis under continuous‐flow conditions, focusing in heterocycle ring formation and highlighting some of the most recent examples found in the literature, as well as some synthetic strategies aiming for the flow preparation of high‐value chemical products, such as APIs and agrochemicals.

ACS Style

Pedro Brandão; Marta Pineiro; Teresa M. V. D. Pinho E Melo. Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis. European Journal of Organic Chemistry 2019, 2019, 7188 -7217.

AMA Style

Pedro Brandão, Marta Pineiro, Teresa M. V. D. Pinho E Melo. Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis. European Journal of Organic Chemistry. 2019; 2019 (43):7188-7217.

Chicago/Turabian Style

Pedro Brandão; Marta Pineiro; Teresa M. V. D. Pinho E Melo. 2019. "Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis." European Journal of Organic Chemistry 2019, no. 43: 7188-7217.

Research article
Published: 09 October 2019 in ACS Omega
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Ring-fused diphenylchlorins as potent low-dose photosensitizers for photodynamic therapy of bladder carcinoma and esophageal adenocarcinoma are described. All studied molecules were very active against HT1376 urinary bladder carcinoma and OE19 esophageal adenocarcinoma cell lines, showing IC50 values below 50 nM. The in vivo evaluation of the more promising photosensitizer, using an OE19 tumor/chick embryo chorioallantoic membrane model, showed a tumor weight regression of 33% with a single photodynamic therapy treatment with the photosensitizer dose as low as 37 ng/embryo.

ACS Style

Bruno Nascimento; Mafalda Laranjo; Nelson A. M. Pereira; João Dias-Ferreira; Marta Pineiro; Maria Filomena Botelho; Teresa M. V. D. Pinho E Melo. Ring-Fused Diphenylchlorins as Potent Photosensitizers for Photodynamic Therapy Applications: In Vitro Tumor Cell Biology and in Vivo Chick Embryo Chorioallantoic Membrane Studies. ACS Omega 2019, 4, 17244 -17250.

AMA Style

Bruno Nascimento, Mafalda Laranjo, Nelson A. M. Pereira, João Dias-Ferreira, Marta Pineiro, Maria Filomena Botelho, Teresa M. V. D. Pinho E Melo. Ring-Fused Diphenylchlorins as Potent Photosensitizers for Photodynamic Therapy Applications: In Vitro Tumor Cell Biology and in Vivo Chick Embryo Chorioallantoic Membrane Studies. ACS Omega. 2019; 4 (17):17244-17250.

Chicago/Turabian Style

Bruno Nascimento; Mafalda Laranjo; Nelson A. M. Pereira; João Dias-Ferreira; Marta Pineiro; Maria Filomena Botelho; Teresa M. V. D. Pinho E Melo. 2019. "Ring-Fused Diphenylchlorins as Potent Photosensitizers for Photodynamic Therapy Applications: In Vitro Tumor Cell Biology and in Vivo Chick Embryo Chorioallantoic Membrane Studies." ACS Omega 4, no. 17: 17244-17250.

Short communication
Published: 30 September 2019 in Dyes and Pigments
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Tryptanthrin, a product present in several natural sources used as colorants and very relevant in the field of Medicinal Chemistry, was synthesized from indigo and isatin under mild conditions using microwave irradiation. A plausible mechanism for the synthesis of tryptanthrin using the oxidant system formed by iodine, sodium hydride and DMF, the latter acting with dual activity as solvent and as the oxygen source, is proposed.

ACS Style

Pedro Brandão; Daniela Ribeiro Pinheiro; Sergio Seixas de Melo; Marta Pineiro. I2/NaH/DMF as oxidant trio for the synthesis of tryptanthrin from indigo or isatin. Dyes and Pigments 2019, 173, 107935 .

AMA Style

Pedro Brandão, Daniela Ribeiro Pinheiro, Sergio Seixas de Melo, Marta Pineiro. I2/NaH/DMF as oxidant trio for the synthesis of tryptanthrin from indigo or isatin. Dyes and Pigments. 2019; 173 ():107935.

Chicago/Turabian Style

Pedro Brandão; Daniela Ribeiro Pinheiro; Sergio Seixas de Melo; Marta Pineiro. 2019. "I2/NaH/DMF as oxidant trio for the synthesis of tryptanthrin from indigo or isatin." Dyes and Pigments 173, no. : 107935.

Journal article
Published: 01 July 2019 in Journal of Porphyrins and Phthalocyanines
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Looking for sustainable synthetic methodologies, mechanochemistry as a new tool for one-step and two-step approaches for the synthesis of meso-substituted porphyrins was explored. The best results were obtained in a two-step procedure, under liquid-assisted grinding in the oxidation step using 2-methyltetrahydrofuran, an environmentally acceptable solvent, and MnO2 as a heterogeneous oxidant. The sustainability was assessed using two sustainability metrics, E-factor and EcoScale, which allow comparison between procedures and methods.

ACS Style

Carla Gomes; Mariana Peixoto; Marta Pineiro. Porphyrin synthesis using mechanochemistry: Sustainability assessment. Journal of Porphyrins and Phthalocyanines 2019, 23, 889 -897.

AMA Style

Carla Gomes, Mariana Peixoto, Marta Pineiro. Porphyrin synthesis using mechanochemistry: Sustainability assessment. Journal of Porphyrins and Phthalocyanines. 2019; 23 (07n08):889-897.

Chicago/Turabian Style

Carla Gomes; Mariana Peixoto; Marta Pineiro. 2019. "Porphyrin synthesis using mechanochemistry: Sustainability assessment." Journal of Porphyrins and Phthalocyanines 23, no. 07n08: 889-897.