Article
Chemistry, Organic
Haiwen Li, Junhu Xin, Yuhang Xue, Cunde Wang
Summary: A pseudo-three-component annulation reaction was investigated to access polysubstituted 5H-chromeno[2,3-b]pyridines. This reaction involved a sequential intermolecular addition/cyclization/epoxidation/ring opening/aromatization sequence, providing an efficient and atom economical approach for the synthesis of 3-hydroxy-5H-chromeno[2,3-b]pyridines from readily available substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Thiago Anjos, Elba L. L. Gutterres, Daniela A. A. Barancelli, Roberta Cargnelutti, Benhur Godoi, Thiago Barcellos, Ricardo F. F. Schumacher
Summary: A synthetic method for organochalcogen-functionalized chromenones has been developed using diorganyl dichalcogenides and alkynyl aryl ketones. Selectfluor(R) mediates the cyclization/organochalcogenation reactions under mild and open-to-air conditions. The versatile methodology allows for the synthesis of organochalcogen-substituted thiochromenone and isocromenone derivatives.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Amr Elagamy, Ranjay Shaw, Chandan Shah, Ramendra Pratap
Summary: An efficient iodine-mediated method has been developed for the synthesis of functionalized 2-(methylthio)-4H-chromen-4-ones, which serve as key precursors for various chemical reactions. Mechanistically, the intramolecular cyclization of ketene dithioacetal was observed to proceed through a radical pathway. 3-Halo-2-(methylthio)-4H-chromen-4-ones were obtained via various two- or one-pot halogenation approaches.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hua-Feng He, Yuwan Wang, Chun Zou, Zheng Tu, Yongquan Xu, Junfeng Yin
Summary: In this study, a series of aryl cyclolactones bearing an exocyclized C=C bond were successfully constructed using aryl propargyl ether and o-iodibenzoic acid as substrates. The reaction showed excellent compatibility and moderate to good yields. A concise mechanism was proposed based on substrate expansion and theoretical analysis.
Article
Chemistry, Multidisciplinary
Hua-Feng He, Yuwan Wang, Chun Zou, Zheng Tu, Yongquan Xu, Junfeng Yin
Summary: A series of aryl cyclolactones bearing an exocyclized C=C bond were successfully constructed from aryl propargyl ether and o-iodibenzoic acid with moderate to good yields. The reaction showed excellent compatibility with diverse substituent groups and a concise mechanism was proposed based on substrate expansion and theoretical analysis.
Article
Chemistry, Organic
Min-Qi Hu, Ying Zhang, Kai-Li Dai, Li-Fang Yu, Ting Liu, Jie Tang, Fan Yang
Summary: A convenient method for constructing 3-(2-methoxypyridin-3-yl)-4H-chromen-4-ones has been successfully developed, with high yields and good functional group compatibility. Further derivatization was achieved through Suzuki-Miyaura cross-coupling reaction, potentially opening up new possibilities for exploring the biological activity of these compounds.
Article
Chemistry, Organic
Yongzhu Liu, Xinxin Qi, Xiao-Feng Wu
Summary: This study presents a palladium-catalyzed straightforward procedure for the synthesis of 3-arylquinolin-2(1H)-ones, which demonstrates moderate to good yields with very good functional group compatibility. The synthesis proceeds through a palladium-catalyzed reductive aminocarbonylation reaction, utilizing benzylic ammonium triflates and o-nitrobenzaldehydes as starting materials.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hai-Tao Yang, Su-Qing Zhou, Dan-Mei Chen, Zi-Jun Hu, Xiao-Qi Qiang, Xiao-Qing Song, Sheng Tan, Wei-Hua Jiang, Yong-Qiang Sun, Chun-Bao Miao
Summary: A copper-catalyzed annulation of O-acyl oximes with cyclic 1,3-diones has been developed, providing a concise synthesis of 7,8-dihydroindolizin-5(6H)-ones and cyclohexanone-fused furans through substituent-controlled selective radical coupling. 2-Alkyl cyclic 1,3-diones undergo C-C radical coupling, while 2-unsubstituted cyclic 1,3-diones undergo C-O radical coupling.
Article
Chemistry, Organic
Sourav Das, Suvam Paul, Tathagata Choudhuri, Papiya Sikdar, Avik Kumar Bagdi
Summary: A simple and efficient visible-light-induced methodology has been developed for the selective synthesis of dihydro-4H-furo[3,2-c]chromen-4-one derivatives via dehydrogenative coupling reaction. The methodology is highly useful for the synthesis of various dihydro-4H-furo[3,2-c]chromen-4-ones from readily accessible reactants under an oxygen atmosphere. Importantly, the study also demonstrates the additive-free approach for this transformation. Mechanistic investigation reveals that the dehydrogenative reaction proceeds via a radical pathway. Additionally, the synthesized dihydro-4H-furo[3,2-c]chromen-4-one can be transformed into different 4H-furo[3,2-c]chromen-4-ones through simple protocols.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Tuan Anh Nguyen Tien, Mariia Miliutina, Jan Radolko, Richard Thom, Tuan T. Dang, Peter Ehlers, Peter Langer
Summary: The domino reaction of amino acid esters with 2-chlorophenylpropynones, which are readily available through Sonogashira reactions, produces novel chromeno[2,3-c]pyrrol-9(2H)-ones. This multi-step reaction involves Michael, Claisen, and SNAr reactions. Some intermediates were isolated, providing insights into the mechanism.
Article
Chemistry, Organic
Reda A. Haggam
Summary: Microwave irradiation is an effective tool for organic reactions, allowing for shorter reaction times and higher yields. In this study, substituted 2-iodobenzophenones were transformed into substituted fluoren-9-ones with yields of 56-92% using microwave irradiation.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Alexey V. Nizovtsev, Anatolii I. Sokolov, Alexander Yu. Smirnov, Andrey A. Mikhaylov, Ivan N. Myasnyanko, Olga A. Belozerova, Nadezhda S. Baleeva, Liliia Usmanova, Mikhail S. Baranov
Summary: A short and general protocol for synthesizing potentially biologically active pyridine-2,6-diones is reported, involving O-alkylation of 5-hydroxy-1,2-oxazine-6-ones to redirect their condensation with primary amines. This manipulation allows the synthesis of a library of over 30 previously undescribed derivatives in yields ranging from 37% to 89%.
Article
Chemistry, Inorganic & Nuclear
Sundarraman Balaji, Gunasekaran Balamurugan, Rengan Ramesh, David Semeril
Summary: A convenient protocol for the one-pot synthesis of quinazolin-4(3H)-ones using palladium(II) complexes via dehydrogenative coupling of benzyl alcohols and 2-aminobenzamide has been described. New structurally related Pd(II) N and O chelating complexes were designed and synthesized, with their formation confirmed by analytical and spectral methods. The study also confirmed the square-planar geometry around the palladium(II) ion and successfully achieved a wide range of substituted quinazolinones.
Article
Chemistry, Organic
Narjes Baharvand, Enayatollah Mottaghinejad, Mohsen Sargordan Fardarani, Reza Hosseini Doust
Summary: In this study, a series of novel compounds were successfully synthesized and characterized. The synthesized compounds exhibited antibacterial activity, suggesting their potential application as antibacterial agents.
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sergey Gritsevich, Alexander Sapegin, Mikhail Krasavin
Summary: In this study, 5,11-Dihydro-6H-dibenzo[b,e]azepin-6-ones were successfully expanded into 5,7,8,14-tetrahydrodibenzo[e,h][1,4]diazecin-9(6H)-ones using the hydrated imidazoline ring expansion (HIRE) method.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Medicinal
Jose X. Soares, Daniela R. P. Loureiro, Ana Laura Dias, Salete Reis, Madalena M. M. Pinto, Carlos M. M. Afonso
Summary: This work provides a comprehensive review of marine xanthones, including their structures, biological activities, and natural sources. Molecular descriptors were used to analyze the chemical space occupied by marine-derived xanthones. Marine xanthone derivatives are rewarding bioactive compounds and hold promise for the design of novel bioactive molecules.
Review
Chemistry, Multidisciplinary
Sandra Mota, Claudia Pinto, Sara Cravo, Joana Rocha e Silva, Carlos Afonso, Jose Manuel Sousa Lobo, Maria Elizabeth Tiritan, Honorina Cidade, Isabel Filipa Almeida
Summary: The cosmetic industry is moving towards the development of more sustainable products, such as utilizing cork and its by-products, which not only meet consumer demand but also contain bioactive compounds with antioxidant activity that can be used in cosmetic products such as anti-aging.
APPLIED SCIENCES-BASEL
(2022)
Article
Chemistry, Medicinal
Ana R. Neves, Luciana C. Gomes, Sara I. Faria, Joao Sousa, Raquel Ruivo, Ines Pascoa, Madalena Pinto, Emilia Sousa, Miguel M. Santos, Elisabete R. Silva, Marta Correia-da-Silva, Filipe Mergulhao
Summary: The development of harmless substances to replace biocide-based coatings used to prevent or manage marine biofouling is urgent. In this study, the anti-biofilm properties of a synthetic polyphenolic compound were explored and found to effectively prevent biofilm formation and reduce pre-formed biofilms. Applying this compound to a marine coating resulted in reduced biofilm cell number, biovolume, and thickness. Furthermore, the compound was found to have no transcriptional activation of selected nuclear receptors, suggesting its eco-friendliness towards marine ecosystems.
Article
Pharmacology & Pharmacy
Sandra Barreiro, Barbara Silva, Solida Long, Madalena Pinto, Fernando Remiao, Emilia Sousa, Renata Silva
Summary: This study suggests that fiscalins have neuroprotective effects against neurodegenerative diseases and potential as new drugs for treatment and prevention.
Article
Biochemistry & Molecular Biology
Ana Rita Neves, Catia Vilas Boas, Catarina Goncalves, Vitor Vasconcelos, Madalena Pinto, Elisabete R. Silva, Emilia Sousa, Joana R. Almeida, Marta Correia-da-Silva
Summary: The researchers successfully improved the antifouling performance of synthesized compounds by optimization while maintaining low ecotoxicity, which could be promising for replacing harmful biocides for antifouling purposes.
BIOORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Marialucia Gallorini, Simone Carradori, Diana I. S. P. Resende, Luciano Saso, Alessia Ricci, Andreia Palmeira, Amelia Cataldi, Madalena Pinto, Emilia Sousa
Summary: Natural products have gained attention for their safety and potential effectiveness as anti-inflammatory drugs. Xanthones, particularly alpha- and gamma-mangostin, have shown antioxidant and anti-inflammatory activities, but their mechanism of action is still only partially understood. Studies on synthesized xanthone derivatives have revealed a close relationship between the xanthone scaffold and Nrf2 activation, which plays a role in the cell's response to oxidative stress and inflammation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Review
Biochemical Research Methods
Carla Fernandes, Rita Lima, Madalena M. M. Pinto, Maria Elizabeth Tiritan
Summary: This review presents the latest advancements in chromatographic supports used for the development of chiral stationary phases (CSPs) in liquid chromatography (LC), with a focus on the advantages and drawbacks of different materials used as chromatographic supports. Recent application examples are also highlighted, emphasizing innovative trends in LC.
JOURNAL OF CHROMATOGRAPHY A
(2022)
Article
Chemistry, Medicinal
Catia Vilas-Boas, Virginia Goncalves, Paolo De Marco, Emilia Sousa, Madalena Pinto, Elisabete R. Silva, Maria Elizabeth Tiritan, Marta Correia-da-Silva
Summary: This study developed a method for quantifying gallic acid persulfate (GAP) in seawater and ultrapure water matrix and evaluated its stability and release performance. The results showed that GAP had good stability and low leaching in different water matrices, highlighting its promising potential as an antifouling coating.
Review
Biochemistry & Molecular Biology
Joana Moreira, Lucilia Saraiva, Madalena M. Pinto, Honorina Cidade
Summary: This article reviews the research progress of diarylpentanoids in the past two decades, including their wide range of biological activities and synthetic methods. The article highlights the diarylpentanoid scaffold as a promising starting point for the development of new therapeutic agents.
Review
Biochemistry & Molecular Biology
Carla Fernandes, Ricardo Ribeiro, Madalena Pinto, Anake Kijjoa
Summary: Cyclopeptides derived from marine sources are important due to their structural diversity and biological activities. The determination of their absolute configurations is challenging, but can be achieved through acidic hydrolysis and liquid chromatography (LC) analysis. Recent works have identified 91 previously unreported marine-derived cyclopeptides, with many displaying anticancer or antimicrobial activities. LC analysis using Marfey's method was the most frequently employed technique for absolute stereochemical assignment.
Review
Biochemistry & Molecular Biology
Carolina Morais Carrico, Maria Elizabeth Tiritan, Honorina Cidade, Carlos Afonso, Joana Rocha e Silva, Isabel F. Almeida
Summary: The growing concerns over climate crisis and depletion of fossil fuels have led to a surge in sustainability trends. Consumer demand for eco-friendly products has been steadily increasing, driven by the desire for environmental protection and preservation for future generations. Cork, a natural product with centuries of history, is primarily used in the wine industry for cork stoppers. However, this process generates by-products such as cork powder and waste that have potential applications in the cosmetic and pharmaceutical industries. This study aims to explore the potential of cork by-products and compile the available methods for their extraction, isolation, identification, and quantification, providing new opportunities for their utilization.
Article
Biochemistry & Molecular Biology
Jose X. Soares, Ines Afonso, Adaleta Omerbasic, Daniela R. P. Loureiro, Madalena M. M. Pinto, Carlos M. M. Afonso
Summary: The emergence of multiresistant bacteria and shortage of antibacterials drives the search for novel agents. Marine natural products, specifically polyketides, have shown promising antibacterial activity. This study identified a dataset of 246 marine polyketides and characterized their chemical space and molecular similarity.
Article
Biochemistry & Molecular Biology
Bruno Horta, Joana Freitas-Silva, Jani Silva, Francisca Dias, Ana Luisa Teixeira, Rui Medeiros, Honorina Cidade, Madalena Pinto, Fatima Cerqueira
Summary: Chalcones have been extensively studied as anticancer agents. Among them, chalcone 16 showed the highest inhibitory effect on tumor cell viability and was selected for further investigation. The results suggest that chalcone 16 may influence macrophage polarization to inhibit cancer.
Article
Infectious Diseases
Mariana C. Almeida, Nikoletta Szemeredi, Fernando Duraes, Solida Long, Diana I. S. P. Resende, Paulo Martins da Costa, Madalena Pinto, Gabriella Spengler, Emilia Sousa
Summary: Drug resistance is becoming a major global health threat, with overexpression of efflux pumps and formation of biofilms being common mechanisms. Therefore, it is crucial to develop antimicrobial agents that can counteract resistance. Pyrazino[2,1-b]quinazoline-3,6-diones have recently been discovered to have relevant antimicrobial properties.
Article
Chemistry, Medicinal
Joana Moreira, Patricia M. A. Silva, Matilde Barros, Lucilia Saraiva, Madalena Pinto, Hassan Bousbaa, Honorina Cidade
Summary: This article reports the design and synthesis of a new chalcone-trimethoxycinnamide hybrid (7) based on two promising antiproliferative compounds (CM-M345 and BP-M345). A new series of 7-analogues was also designed and synthesized to expand the structure-activity relationship (SAR) knowledge. The antitumor activity of these compounds was evaluated against melanoma, breast adenocarcinoma, colorectal carcinoma, and non-tumor cells. Compound 7 showed potent antiproliferative activity on colorectal tumor cells, and its mechanism of action was found to be p53-independent and involved inducing mitotic arrest and cell death.