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Selective synthesis of 3-(1H-Tetrazol-5-yl)-indoles from 2H-Azirines and Arynes
Grosso, Carla; Alves, Cláudia; Sase, Terver J.; Alves, Nuno G.; Cardoso, Ana L.; Melo, Teresa M. V. D. Pinho e; Lemos, AmericoA new selective synthetic approach to indole derivatives bearing a tetrazole moiety has been developed. Arynes, generated in situ from o-(trimethylsilyl)aryl triflates and KF, reacted smoothly with 2-(2-benzyl-2H-tetrazol-5-yl)-2H-azirines to give 3-(2-benzyl-2H-tetrazol-5-yl)-indole derivatives with high selectivity. Deprotection of the tetrazole moiety gave 3-(1H-tetrazol-5-yl)-indole derivatives.
Reactivity of ethyl nitrosoacrylate toward pyrrole, indole and pyrrolo[3,2-c]ca...
Benzi, Alice; Lopes, Susana M. M.; Nunes, Sandra; Giorgi, Gianluca; Bianchi, Lara; Tavani, Cinzia; Pais, Alberto; Petrillo, GiovanniNitrosoalkenes react with 8-methyl-1,6-dihydropyrrolo[3,2-c]carbazole to give both 2- and 3-alkylated products via hetero-Diels-Alder reaction followed by the cycloadduct ring-opening. Quantum chemical calculations, at DFT level of theory, were carried out to investigate the regioselectivity of the cycloaddition of ethyl nitrosoacrylate with 1,6-dihydropyrrolo[3,2-c]carbazoles as well as with pyrrole and indole...
Cholesteryl hemiazelate identified in CVD patients causes in vitro and in vivo ...
Domingues, Neuza S.; Gaifem, Joana; Matthiesen, Rune; Saraiva, Diana P.; Bento, Luís; Marques, André R. A.; Soares, Maria I. L.; Sampaio, JulioOxidation of PUFAs in LDLs trapped in the arterial intima plays a critical role in atherosclerosis. Though there have been many studies on the atherogenicity of oxidized derivatives of PUFA-esters of cholesterol, the effects of cholesteryl hemiesters (ChEs), the oxidation end products of these esters, have not been studied. Through lipidomics analyses, we identified and quantified two ChE types in the plasma of...
Ethyl 7-Acetyl-8a-methyl-3-(1-phenyl-1H-tetrazol-5-yl)-1,4,4a,5,6,8a-hexahydro-...
Lopes, Susana M. M.; Lemos, Américo; Paixão, José A.; Melo, Teresa M. V. D. Pinho eThe Diels–Alder reaction of ethyl 3-(1-phenyl-1H-tetrazol-5-yl-1,2-diaza-1,3-butadiene- 1-carboxylate with 2-acetyl-6-methyl-2,3-dihydro-4H-pyran (methyl vinyl ketone dimer) regios- electively afforded the corresponding 3-(tetrazol-5-yl)-hexahydro-7H-pyrano[2,3-c]pyridazine in quantitative yield. An X-ray crystal structure of this cycloadduct is reported.
Color Polymorphs of ROY-ol
Nogueira, Bernardo A.; Lopes, Susana M. M.; Milani, Alberto; André, Vânia; Paixão, José A.; Eusébio, M. Ermelinda S.; Melo, Teresa M. V. D. Pinho eColor polymorphism is a fascinating property exhibited by compounds that have polymorphs of different colors. The most famous family of substances forming molecular organic color polymorphs is the ROY family of compounds. ROY, which states for the red, orange, and yellow colors of the polymorphs of 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carbonitrile, is currently the compound exhibiting the largest number...
Diels-Alder Cycloaddition Reactions in Sustainable Media
Soares, Maria I. L.; Cardoso, Ana L.; Melo, Teresa M. V. D. Pinho eDiels-Alder cycloaddition reaction is one of the most powerful strategies for the construction of six-membered carbocyclic and heterocyclic systems, in most cases with high regio- and stereoselectivity. In this review, an insight into the most relevant advances on sustainable Diels-Alder reactions since 2010 is provided. Various environmentally benign solvent systems are discussed, namely bio-based derived solv...
Unveiling a family of spiro-β-lactams with anti-HIV and antiplasmodial activity...
Alves, Américo J. S.; Alves, Nuno G.; Bártolo, Inês; Fontinha, Diana; Caetano, Soraia; Prudêncio, Miguel; Taveira, Nuno; Melo, Teresa M. V. D. Pinho eThe molecular architecture of spirocyclic compounds has been widely explored within the medicinal chemistry field to obtain new compounds with singular three-dimensional pharmacophoric features and improved bioactivity. Herein, the synthesis of 68 new spirocyclopentene-β-lactams is described, resulting from a rational drug design and structural modulation of a highly promising lead compound BSS-730A, previously...
High instantaneous inhibitory potential of Bictegravir and the new Spiro-β-Lact...
Bártolo, Inês; Moranguinho, Inês; Gonçalves, Paloma; Diniz, Ana Rita; Borrego, Pedro; Martin, Francisco; Figueiredo, Inês; Gomes, PerpétuaIntegrase inhibitors (INIs) are an important class of drugs for treating HIV-2 infection, given the limited number of drugs active against this virus. While the clinical efficacy of raltegravir and dolutegravir is well established, the clinical efficacy of bictegravir for treating HIV-2 infected patients has not been determined. Little information is available regarding the activity of bictegravir against HIV-2...
A selective p53 activator and anticancer agent to improve colorectal cancer the...
Ramos, Helena; Soares, Maria I. L.; Silva, Joana; Raimundo, Liliana; Calheiros, Juliana; Gomes, Célia; Reis, Flávio; Monteiro, Filipe A.; Nunes, CláudiaImpairment of the p53 pathway is a critical event in cancer. Therefore, reestablishing p53 activity has become one of the most appealing anticancer therapeutic strategies. Here, we disclose the p53-activating anticancer drug (3S)-6,7-bis(hydroxymethyl)-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole (MANIO). MANIO demonstrates a notable selectivity to the p53 pathway, activating wild-type (WT)p53 and restoring W...
Platinum(II) ring-fused chlorins as efficient theranostic agents: Dyes for tumo...
Laranjo, Mafalda; Aguiar, Márcia Campos; Pereira, Nelson A. M.; Brites, Gonçalo; Nascimento, Bruno F. O.; Brito, Ana F.; Casalta-Lopes, JoãoThe discovery of Pt-chlorin-type theranostic agents is described. Luminescent Pt(II) 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused chlorins, with different degrees of hydrophilicity, have been synthesized and their in vitro photocytotoxicity against human melanoma, oesophageal and bladder carcinomas was studied. A di(hydroxymethyl)-substituted chlorin was identified as a privileged molecule to explore imaging...