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Solvent-Driven Self-Organization of Meso-Substituted Porphyrins: Morphological ...

Costa, Telma; Peixoto, Mariana; Pineiro, Marta; Melo, J. Sérgio Seixas de

A morphological analysis of different thin films of meso-tetra-p-(di-p-phenylamino)phenylporphyrin, H2T(TPA)4P, was made by fluorescence lifetime imaging microscopy (FLIM) and scanning electron microscopy (SEM). A comprehensive study of H2T(TPA)4P was undertaken through UV/vis absorption and fluorescence techniques in different solvents, solvent mixtures and in thin films. In solution, occurrence of intramolecu...


Applications of Photodynamic Therapy in Endometrial Diseases

Correia-Barros, Gabriela; Serambeque, Beatriz; Carvalho, Maria João; Marto, Carlos Miguel; Pineiro, Marta; Pinho e Melo, Teresa M. V. D.

Photodynamic therapy (PDT) is a medical procedure useful for several benign conditions (such as wound healing and infections) and cancer. PDT is minimally invasive, presents few side effects, good scaring, and is able to minimal tissue destruction maintaining organ anatomy and function. Endoscopic access to the uterus puts PDT in the spotlight for endometrial disease treatment. This work systematically reviews ...


Ring-Fused meso-Tetraarylchlorins as Auspicious PDT Sensitizers: Synthesis, Str...

Laranjo, Mafalda; Pereira, Nelson A. M.; Oliveira, Andreia S. R.; Aguiar, Márcia Campos; Brites, Gonçalo Sousa; Nascimento, Bruno F. O.

Novel 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused meso-tetraarylchlorins, with different degrees of hydrophilicity (with methyl ester, hydroxymethyl, and carboxylic acid moieties), have been synthesized and their photophysical characterization as well as in vitro photocytotoxicity assessment against human melanoma and esophageal and bladder carcinomas was carried out. An integrated analysis of the photosens...


Tryptanthrin and Its Derivatives in Drug Discovery: Synthetic Insights

Brandão, Pedro; Pineiro, Marta; Burke, Anthony J.

Tryptanthrin is a golden-yellow, naturally occurring alkaloid that can be obtained from multiple sources and through different synthetic methodologies. This tetracyclic compound displays several relevant biological activities. The potential of this tetracyclic alkaloid has been widely explored, and several researchers have focused their attention on expanding the variety of tryptanthrin derivatives by using a r...


The application of isatin-based multicomponent-reactions in the quest for new b...

Brandão, Pedro; Marques, Carolina S.; Burke, Anthony J.; Pineiro, Marta

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 li- braries fast and with wide scaffold diversity. In this review, we address those recent developments, explo...


Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural...

Brandão, Pedro; Marques, Carolina S.; Carreiro, Elisabete P.; Pineiro, Marta; Burke, Anthony J.

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 eve...


Petasis adducts of tryptanthrin – synthesis, biological activity evaluation and...

Burke, Anthony; Marques, Carolina; Brandão, Pedro; Pineiro, Marta; Eugenia, Pinto

Tryptanthrin is a valuable tetracyclic alkaloid, which displays a wide variety of biological activities. The application of this type of scaffold as a starting material for the discovery of new drug candidates is of major importance in medicinal chemistry. In this work, we report one of the few examples of tryptanthrin-based multicomponent reaction approaches for drug discovery, and the first using the Petasis ...


Ugi reaction synthesis of oxindole-lactam hybrids as selective butyrylcholinest...

Burke, Anthony; Brandão, Predro; Pineiro, Marta; Stark, Holger; Lopez, Oscar; Fernández-Bolaños, José; Leitzbach, Luisa

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-...


Deep in blue with green chemistry: influence of solvent and chain length on the...

Pinheiro, Daniela; Pineiro, Marta; Galvão, Adelino M.; Melo, J. Sérgio Seixas de

Using green chemistry procedures the synthesis of N-alkyl (NCnInd) and N,N′-dialkyl (N,N′CnInd) indigo derivatives, with n = 1–3, 6, 8, 12 and 18, was undertaken, leading to compounds with blueish to greenish colors in solution. The effect of the alkyl chain length on the spectral (including color) and photophysical properties of the compounds was explored. This was done with solvents of different viscosities a...


The application of isatin-based multicomponent-reactions in the quest for new b...

Brandão, Pedro; Marques, Carolina; Burke, Anthony J.; Pineiro, Marta

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, explori...


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